Olanzapine

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Olanzapine

Systematic (IUPAC) name

2-methyl-4-(4-methyl-1-piperazinyl)-

10H-thieno[2,3-b][1,5]benzodiazepine

Identifiers

CAS number 132539-06-1

ATC code N05AH03

PubChem CID 4585

IUPHAR ligand 47
ID

DrugBank DB00334

ChemSpider 10442212

Chemical data

Formula C17H20N4S

Mol. mass 312.439

SMILES eMolecules & PubChem

Physical data

Melt. point 195 °C (383 °F)

Solubility in Practically insoluble in water mg/mL

water (20 °C)

Pharmacokinetic data

Bioavailability 87% [1]

Metabolism Hepatic (direct glucuronidation and CYP

mediated oxidation)

Half-life 21–54 hours

Excretion urine 57%, feces 30%

Therapeutic considerations

Pregnancy cat. C
 Legal status ℞ Prescription only

Routes oral, intramuscular

Y(what is this?) (verify)

Zyprexa 10 mg tablets (AU)

Olanzapine (trade names Zyprexa, Zalasta, Zolafren, Olzapin, Rexapin, Zypadhera or in
combination with fluoxetine Symbyax) is an atypical antipsychotic, approved by the FDA for
the treatment of schizophrenia and bipolar disorder.[2] The olanzapine formulations are
manufactured and marketed by the pharmaceutical company Eli Lilly and Company, whose
patent for olanzapine proper expires in 2011 (in October 2009 a Canadian judge ruled that the
1991 patent was invalid).[3] Sales of Zyprexa in 2008 were $2.2B in the US alone, and $4.7B in
total.[4]

Contents
[hide]
• 1 Indications and Usage
○ 1.1 Off-label uses
 1.1.1 Prevention of psychosis
 1.1.2 Use in elderly
• 2 Dosage and administration
• 3 Pharmacology
• 4 Metabolism
• 5 Side effects, adverse reactions
○ 5.1 Metabolic effects
○ 5.2 Animal Toxicology
• 6 Overdose
 • 7 Controversy, lawsuits and settlements
• 8 Chemistry
• 9 See also
• 10 Notes and references
• 11 External links
○ 11.1 Manufacturer site
○ 11.2 Consumer information
○ 11.3 Controversy

[edit] Indications and Usage

• oral formulation: acute and maintenance treatment of Schizophrenia in adults, acute
treatment of manic or mixed episodes associated with Bipolar I Disorder (monotherapy
and in combination with lithium or valproate)
• intramuscular formulation: acute agitation associated with Schizophrenia and Bipolar I
Mania in adults
• oral formulation combined with fluoxetine: acute treatment of depressive episodes
associated with Bipolar I Disorder in adults, or acute treatment of treatment resistant
depression in adults [5]
Known FDA approvals are as follows:
• approved for the treatment of the manifestations of psychotic disorders on September 6,
1996[6]
• approved in combination with fluoxetine for the treatment of depressive episodes
associated with Bipolar disorder on December 24, 2003[7]
• approved for the long-term treatment of bipolar I disorder on January 14, 2004[8]
• approved in combination with fluoxetine for treatment resistant depression on March 19,
2009.[9]
[edit] Off-label uses
Case-reports, open-label, and small pilot studies suggest efficacy of olanzapine for the treatment
of some anxiety spectrum disorders (e.g. generalized anxiety disorder,[10] panic disorder,[11] post-
traumatic stress disorder);[12] however, olanzapine has not been rigorously evaluated in
randomized, placebo-controlled trials for this use and is not FDA approved for these indications.
Other common off-label uses of olanzapine include the treatment of eating disorders (e.g.
anorexia nervosa) and as an adjunctive treatment for major depressive disorder without psychotic
features. It has also been used for Tourette syndrome and stuttering.[13] Olanzapine is also used in
many addiction clinics as a sleep aid (usually 2.5–5 mg) due to its low abuse profile and zero
addictive properties.[14]
[edit] Prevention of psychosis
Olanzapine has been considered as part of an early psychosis approach for schizophrenia. The
Prevention through Risk Identification, Management, and Education (PRIME) study, funded by
the National Institute of Mental Health and Eli Lilly, tested the hypothesis that olanzapine might
prevent the onset of psychosis in people at very high risk for schizophrenia. The study examined
60 patients with prodromal schizophrenia, who were at an estimated risk of 36–54% of
developing schizophrenia within a year, and treated half with olanzapine and half with placebo.
[15]
In this study, patients receiving olanzapine had a lower risk of progressing to psychosis,
although the difference did not reach statistical significance. Olanzapine was effective for
treating the prodromal symptoms, but was associated with significant weight gain.[16]
[edit] Use in elderly
Citing an increased risk of stroke, in 2004 the Committee on the Safety of Medicines (CSM) in
the UK issued a warning that olanzapine and risperidone, both atypical antipsychotic
medications, should not be given to elderly patients with dementia. In the U.S., olanzapine
comes with a black box warning for increased risk of death in elderly patients. It is not approved
for use in patients with dementia-related psychosis.[17] However, a BBC investigation in June
2008 found that this advice was being widely ignored by British doctors.[18]
[edit] Dosage and administration
Olanzapine is available as a tablet in strengths of 2.5 mg, 5 mg, 7.5 mg, 10 mg, 15 mg and
20 mg. It also comes as an orally disintegrating wafer (known as Zydis), which dissolves on the
tongue, in strengths of 5 mg, 10 mg, 15 mg and 20 mg. It is also available as a 10 mg vial for a
rapid-acting intramuscular injection for short-term acute use.
Dose may be adjusted depending on the person' response to the drug. The dose also will depend
on certain medical problems the person may have. It is generally recommended to be taken once
daily before bed as it is highly sedating. However, sedation tends to diminish as treatment is
pursued.
[edit] Pharmacology
Olanzapine is structurally similar to clozapine, but is classified as a thienobenzodiazepine.
Olanzapine has a higher affinity for 5-HT2 serotonin receptors than D2 dopamine receptors.
Like most atypical antipsychotics, compared to the older typical ones, olanzapine has a lower
affinity for histamine, cholinergic muscarinic and alpha adrenergic receptors. Olanzapine also
exhibits weak affinity for GABAA, BZD receptor site[19] which may contribute slightly to its
sedating properties.[20] The mode of action of olanzapine's antipsychotic activity is unknown. It
may involve antagonism at serotonin receptors. Antagonism of dopamine receptors is associated
with extrapyramidal effects such as tardive dyskinesia, and with therapeutic effects.
Antagonizing H1 histamine receptors causes sedation and may cause weight gain, although
antagonistic actions at 5-HT2C receptors have also been implicated in weight gain.
[edit] Metabolism
Olanzapine is metabolized by the cytochrome P450 system isoenzymes 1A2 and 2D6 (minor
pathway). Drug metabolism may be decreased or increased by agents that induce (e.g. cigarette
smoke) or inhibit (e.g. fluvoxamine or ciprofloxacin) CYP1A2 activity respectively.
[edit] Side effects, adverse reactions
This article may contain original research. Please improve it by verifying the claims
made and adding references. Statements consisting only of original research may be
removed. More details may be available on the talk page. (September 2009)
As with all neuroleptic drugs, olanzapine can cause tardive dyskinesia and rare, but life-
threatening, neuroleptic malignant syndrome.
Other recognised side effects may include:
• Restlessness
• akathisia inability to remain still[21]
• dry mouth
• dizziness
• irritability
• sedation
• insomnia
• constipation
• urinary retention
• orthostatic hypotension
• weight gain
• increased appetite
• runny nose
• low blood pressure
• impaired judgment, thinking, and motor skills
• impaired spatial orientation
• impaired responses to senses
• seizure
• trouble swallowing
• dental problems and discoloration of teeth
• missed periods
• problems with keeping body temperature regulated
• apathy, lack of emotion
• Endocrine side effects have included hyperprolactinemia, hyperglycemia, and diabetes
mellitus
• Hyperprolactinemia causing sexual dysfunction, menstrual irregularities, and
osteoporosis
[edit] Metabolic effects
The Food and Drug Administration requires all atypical antipsychotics to include a warning
about the risk of developing hyperglycemia and diabetes, both of which are factors in the
metabolic syndrome. These effects may be related to the drugs' ability to induce weight gain,
although there are some reports of metabolic changes in the absence of weight gain.[citation needed] Of
all the atypical antipsychotics, olanzapine is one of the most likely to induce weight gain based
on various measures.[22][23][24][25] The effect is not dose dependent. [dubious – discuss] Olanzapine may
directly affect adipocyte function, promoting fat deposition.[26] There are some case reports of
olanzapine-induced diabetic ketoacidosis.[27] Olanzapine may decrease insulin sensitivity[28]
though one 3-week study seems to refute this.[29] It may also increase triglyceride levels.[23]
Despite weight gain, a large multi-center randomized National Institute of Mental Health study
found that olanzapine was better at controlling symptoms because patients were more likely to
remain on olanzapine than the other drugs.[30] One small, open-label, non-randomized study
suggest that taking olanzapine by orally dissolving tablets may induce less weight gain,[31] but
this has not been substantiated in a blinded experimental setting.
[edit] Animal Toxicology
In a placebo-compared study of six Macaque monkeys receiving olanzapine between 17 and 27
months, a significant brain volume and weight decreases (8-11%) were detected.[32] In latter
studies of the stored samples, the changes were attributed to astrocyte and oligodendrocyte loss,
[33]
with the neurons spared but positioned more closely compared to the controls. [clarification needed]
However according to this study the neurons does not seem to be completeley spared. The gray
matter shrinking found was 14.6%, but the neuron density increase was only 10.2% which
corresponds to approximately a loss of 5% of the neurons.[citation needed]
Olanzapine has demonstrated carcinogenic effects in multiple studies when exposed chronically
to female mice and rats, but not male mice and rats. The tumors found were in either the liver or
mammary glands of the animals.[34]
[edit] Overdose
Symptoms of an overdose include tachycardia, agitation, dysarthria, decreased consciousness
and coma. Death has been reported after an acute overdose of 450 mg, but also survival after an
acute overdose of 1500 mg.[35] There is no known specific antidote for olanzapine overdose, and
even physicians are recommended to call a certified poison control center for information on the
treatment of such a case.[35]
[edit] Controversy, lawsuits and settlements
Further information: Eli Lilly Controversy
According to a New York Times article published on December 17, 2006,[36] "Eli Lilly has
engaged in a decade-long effort to play down the health risks of Zyprexa, its best-selling
medication for schizophrenia, according to hundreds of internal Lilly documents and e-mail
messages among top company managers", most of which had been disclosed as the result of
lawsuits by individuals who had taken the drug against the company though some had been
stolen.[37] These had been sent to a number of journalists by a lawyer advocate for individuals
with a psychiatric diagnosis opposed to forced psychiatric treatment. Eli Lilly filed a protection
order to stop the dissemination of certain Eli Lilly documents about Zyprexa which they, and the
judge, believed to be confidential and "not generally appropriate for public consumption".[37]
Temporary injunctions required those who had been received the documents to return them and
that the documents be removed from websites which had posted them.[38] In his final judgement,
Judge Weinstein issued a permanent judgement against further dissemination of the documents
and requiring their return by a number of parties named by Lilly.[37] These health risks include an
increased risk for diabetes through Zyprexa's links to obesity and its tendency to raise blood
sugar. Zyprexa is Lilly’s top-selling drug, with sales of $4.2 billion last year.
The documents, given to The New York Times by Jim Gottstein, show that Lilly executives kept
important information from doctors about Zyprexa’s links to obesity and its tendency to raise
blood sugar — both known risk factors for diabetes. The Times of London also obtained copies
of the documents and reported that as early as October 1998, Lilly considered the risk of drug-
induced obesity to be a "top threat" to Zyprexa sales.[39] In another document, dated October 9,
2000, senior Lilly research physician Robert Baker noted that an academic advisory board he
belonged to was "quite impressed by the magnitude of weight gain on olanzapine and
implications for glucose."[39]
Lilly’s own published data, which it told its sales representatives to play down in conversations
with doctors, has shown that 30 percent of patients taking Zyprexa gain 22 pounds or more after
a year on the drug, another study showed 16% of Zyprexa patients gained at least 30 kg (66
pounds) in one year, and some patients have reported gaining 100 pounds or more. But Lilly was
concerned that Zyprexa’s sales would be hurt if the company was more forthright about the fact
that the drug might cause unmanageable weight gain or diabetes, according to the documents,
which cover the period 1995 to 2004. In 2006, Lilly paid $700 million to settle 8,000 lawsuits
from people who said they had developed diabetes or other diseases after taking Zyprexa.
Thousands more suits are still pending.[40]
In 2002, British and Japanese regulatory agencies warned that Zyprexa may be linked to
diabetes, but even after the FDA issued a similar warning in 2003, Lilly did not publicly disclose
their own findings.
Eli Lilly agreed on January 4, 2007 to pay up to $500 million to settle 18,000 lawsuits from
people who claimed they developed diabetes or other diseases after taking Zyprexa. Including
earlier settlements over Zyprexa, Lilly has now agreed to pay at least $1.2 billion to 28,500
people who claim they were injured by the drug. At least 1,200 suits are still pending, the
company said. About 20 million people worldwide have taken Zyprexa since its introduction in
1996.[41] On January 8, 2007, Judge Jack B. Weinstein refused the Electronic Frontier
Foundation's motion to stay his order.[42]
On January 15, 2009 Eli Lilly plead guilty to a misdemeanor charge of illegally marketing
Zyprexa for off-label use, and agreed to pay $1.4 billion.[43] Although Lilly had evidence that it is
not effective for dementia, Zyprexa was marketed for elderly Alzheimer's patients.[44] The drug
carries an F.D.A. warning that it increases the risk of death in older patients with dementia-
related psychosis.[45]
In order to make up for the costs for settling the lawsuits and shrinking sales figures for Zyprexa
in the U.S.A. the company increased the prices for this medication in Germany in May 2007 by
18 percent. [46][47]
[edit] Chemistry
http://www.google.com/patents/about?id=ZGYeAAAAEBAJ&dq=US+5229382

[edit] See also

• Antipsychotics
• Eli Lilly and Company
[edit] Notes and references
1. ^ Burton, Michael E.; Shaw, Leslie M.; Schentag, Jerome J.; Evans, William E. (May 1, 2005).
Applied Pharmacokinetics & Pharmacodynamics: Principles of Therapeutic Drug Monitoring.
Lippincott Williams & Wilkins; Fourth Edition edition. pp. 815. ISBN 978-0781744317.
2. ^ "Olanzapine Prescribing Information" (PDF). Eli Lilly and Company. 2009-03-19.
http://pi.lilly.com/us/zyprexa-pi.pdf. Retrieved 2009-09-06.
3. ^ Pharmalot.com
4. ^ "Lilly 2008 Annual Report" (PDF). Lilly. 2009.
http://files.shareholder.com/downloads/LLY/696621960x0x296463/611E167A-61C9-4C03-
8866-ACF5FA7C8953/English.PDF. Retrieved 2009-08-06.
5. ^ treatment resistant depression defined as Major Depressive Disorder in adult patients who do
not respond to two separate trials of different antidepressants of adequate dose and duration in the
current episode
6. ^ "NDA 20-592" (PDF). Food and Drug Administration. 1996-09-06.
http://www.accessdata.fda.gov/drugsatfda_docs/nda/96/020592_Original_Approval_Pkg%20.pdf.
Retrieved 2009-09-06.
7. ^ "NDA 21-520" (PDF). Food and Drug Administration. 2003-12-24.
http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2003/21520ltr.pdf. Retrieved 2009-09-
06.
8. ^ "NDA 20-592 / S-019" (PDF). Food and Drug Administration. 2004-01-14.
http://www.accessdata.fda.gov/drugsatfda_docs/appletter/2004/20592se1-019ltr.pdf. Retrieved
2009-09-06.
9. ^ Forbes.com
10.^ Pollack MH, Simon NM, Zalta AK, Worthington JJ, Hoge EA, Mick E, Kinrys G,
Oppenheimer J. (2006). "Olanzapine augmentation of fluoxetine for refractory generalized
anxiety disorder: a placebo controlled study.". Biol Psychiatry. 59 (3): 211–5.
doi:10.1016/j.biopsych.2005.07.005. PMID 16139813.
11.^ Sepede G, De Berardis D, Gambi F, Campanella D, La Rovere R, D'Amico M, Cicconetti A,
Penna L, Peca S, Carano A, Mancini E, Salerno RM, Ferro FM. (2003). "Olanzapine
augmentation in treatment-resistant panic disorder: a 12-week, fixed-dose, open-label trial.". J
Clin Psychopharmacol. 107 (5): 394–6. PMID 16415705.
12.^ Jakovljević M, Sagud M, Mihaljević-Peles A. (2006). "Olanzapine in the treatment-resistant,
combat-related PTSD—a series of case reports.". Acta Psychiatrica Scandinavica 26 (1): 45–9.
doi:10.1111/j.1600-0447.1951.tb10961.x. PMID 12752037.
13.^ Stuttering Foundation of America - A look at genetic and neurological correlates of stuttering
14.^ "Antiphyscotic used as sleeping pill".
http://www.forbes.com/2004/09/08/cx_mh_0908seroquel.html. Retrieved 2005-12-11.
15.^ McGlashan, T.H.; et al. (1 May 2003). "The PRIME North America randomized double-blind
clinical trial of olanzapine versus placebo in patients at risk of being prodromally symptomatic
for psychosis. I. Study rationale and design". Schizophrenia Research (Amsterdam: Elsevier) 61
(1): 7–18. doi:10.1016/S0920-9964(02)00439-5. PMID 12648731.
16.^ McGlashan, Thomas H.; et al. (May 2006). "Randomized, double-blind trial of olanzapine
versus placebo in patients prodromally symptomatic for psychosis". American Journal of
Psychiatry (Arlington, VA: American Psychiatric Association) 163 (5): 790–99.
doi:10.1176/appi.ajp.163.5.790. PMID 16648318.
http://ajp.psychiatryonline.org/cgi/content/full/163/5/790. Retrieved 2007-12-03.
17.^ "Important Safety Information for Olanzapine". Zyprexa package insert. Eli Lilly & Company.
2007. http://zyprexa.com/common_pages/safety.jsp. Retrieved 2007-12-03. "Elderly patients with
dementia-related psychosis treated with atypical antipsychotic drugs are at an increased risk of
death compared to placebo. [...] ZYPREXA (olanzapine) is not approved for the treatment of
elderly patients with dementia-related psychosis."
18.^ "Doctors 'ignoring drugs warning'". BBC News. 17 June 2008.
http://news.bbc.co.uk/1/hi/programmes/file_on_4/7457132.stm. Retrieved 2008-06-22.
19.^ RXlist.com
20.^ Cancer.gov Definition of Olanzapine - National Cancer Institute
21.^ Makkos Z, Csonka A (December 2006). "[Akathisia in the course of olanzapine treatment]" (in
Hungarian). Neuropsychopharmacol Hung 8 (4): 215–7. PMID 17211056.
22.^ Moyer, Paula (2005-10-25). "CAFE Study Shows Varying Benefits Among Atypical
Antipsychotics". Medscape Medical News (WebMD).
http://www.medscape.com/viewarticle/515435. Retrieved 2007-12-03.
23.^ a b AstraZeneca Pharmaceuticals (4 April 2006). "Efficacy and Tolerability of Olanzapine,
Quetiapine and Risperidone in the Treatment of First Episode Psychosis: A Randomised Double
Blind 52 Week Comparison". AstraZeneca Clinical Trials. AstraZeneca PLC.
http://www.astrazenecaclinicaltrials.com/Article/526695.aspx. Retrieved 2007-12-03. "At week
12, the olanzapine-treated group had more weight gain, a higher increase in [ body mass index ],
and a higher proportion of patients with a BMI increase of at least 1 unit compared with the
quetiapine and risperidone groups (p<=0.01)."
24.^ Wirshing DA, Wirshing WC, Kysar L, Berisford MA. (1999) Novel antipsychotics: comparison
of weight gain liabilities. Journal of Clinical Psychology 60 358-63
25.^ National Institute of Mental Health (19 September 2005). "NIMH study to guide treatment
choices for schizophrenia". Press release. http://www.eurekalert.org/pub_releases/2005-09/niom-
nst091905.php. Retrieved 2006-12-18.
26.^ Engl J, Rettenbacher M, Fleischhacker WW, Ebenbichler CF (2007). "Atypical antipsychotic
drugs directly impair insulin action in adipocytes: effects on glucose transport, lipogenesis, and
antilipolysis.". Neuropsychopharmacology. Nov;32(11):2431-2; author reply 2433-4. 32 (11):
2431–2.
27.^ Fulbright, April R.; Breedlove, K. T. (2006). "Complete Resolution of Olanzapine-Induced
Diabetic Ketoacidosis" (abstract). Journal of Pharmacy Practice (Thousand Oaks, CA: SAGE
Publications) 19 (4): 255–258. doi:10.1177/0897190006294180.
http://jpp.sagepub.com/cgi/content/abstract/19/4/255. Retrieved 2007-12-02. "Olanzapine has
been associated with diabetic ketoacidosis and also with weight gain, lipid abnormalities, and the
development of type 2 diabetes.".
28.^ Sacher J, Mossaheb N, Spindelegger C, Klein N, Geiss-Granadia T, Sauermann R, Lackner E,
Joukhadar C, Müller M, Kasper S., J; Mossaheb, N; Spindelegger, C; Klein, N; Geiss-Granadia,
T; Sauermann, R; Lackner, E; Joukhadar, C et al. (2008). "Effects of olanzapine and ziprasidone
on glucose tolerance in healthy volunteers.". Neuropsychopharmacology 33 (7): 1633–41.
doi:10.1038/sj.npp.1301541. PMID 17712347.
29.^ Sowell, Margaret; et al. (August 8, 2003). "Evaluation of Insulin Sensitivity in Healthy
Volunteers Treated with Olanzapine, Risperidone, or Placebo: A Prospective, Randomised Study
Using the Two-Step Hyperinsulinemic, Euglycemic Clamp". Journal of Clinical Endocrinology
& Metabolism (The Endocrine Society) 88 (12): 5875–5880. doi:10.1210/jc.2002-021884.
PMID 14671184. http://jcem.endojournals.org/cgi/content/full/88/12/5875. Retrieved 2007-12-
02. "In summary, this study did not demonstrate significant changes in insulin sensitivity in
healthy subjects after 3 wk of treatment with olanzapine or risperidone.".
30.^ Carey, Benedict (September 20, 2005). "Little Difference Found in Schizophrenia Drugs". New
York Times (The New York Times Company).
http://www.nytimes.com/2005/09/20/health/psychology/20drug.html. Retrieved 2007-12-03.
31.^ de Haan L, van Amelsvoort T, Rosien K, Linszen D (2004). "Weight loss after switching from
conventional olanzapine tablets to orally disintegrating olanzapine tablets". Psychopharmacology
(Berl) 175 (3): 389–90. doi:10.1007/s00213-004-1951-2. PMID 15322727.
32.^ Dorph-Petersen KA, Pierri JN, Perel JM, Sun Z, Sampson AR, Lewis DA (September 2005).
"The influence of chronic exposure to antipsychotic medications on brain size before and after
tissue fixation: a comparison of haloperidol and olanzapine in macaque monkeys".
Neuropsychopharmacology 30 (9): 1649–61. doi:10.1038/sj.npp.1300710. PMID 15756305.
33.^ Konopaske GT, Dorph-Petersen KA, Sweet RA, Pierri JN, Zhang W, Sampson AR, Lewis DA
(April 2008). "Effect of chronic antipsychotic exposure on astrocyte and oligodendrocyte
numbers in macaque monkeys". Biol. Psychiatry 63 (8): 759–65.
 doi:10.1016/j.biopsych.2007.08.018. PMID 17945195. PMC 2386415.
http://linkinghub.elsevier.com/retrieve/pii/S0006-3223(07)00847-5.
34.^ Giovanni Brambilla, Francesca Mattioli, Antonietta Martelli (June 2009). "Genotoxic and
carcinogenic effects of antipsychotics and antidepressants". Toxicology 261 (3): 77–88.
doi:10.1016/j.tox.2009.04.056. PMID 19410629.
http://linkinghub.elsevier.com/retrieve/pii/S0300-483X(09)00232-7.
35.^ a b "Symbyax (Olanzapine and fluoxetine) drug overdose and contraindication information".
RxList: The Internet Drug Index. WebMD. 2007.
http://www.rxlist.com/cgi/generic/symbyax_od.htm. Retrieved 2007-12-03.
36.^ The New York Times December 17, 2006
37.^ a b c U:\Cases\Civil L-Z\In re Zyprexa\Documents Leak\Injunction Memo & Order\FINAL
INJUNCTION MEMO 2.13.07.wpd
38.^ EFF.org
39.^ a b Eli Lilly was Concerned by Zyprexa Side-Effects from 1998, The Times (London), January
23, 2007
40.^ NYtimes.com Mother Wonders if Psychosis Drug Helped Kill Son, New York Times, January
4, 2007
41.^ NYtimes.com Lilly to Pay Up to $500 Million to Settle Claims. The New York Times, January
4, 2007
42.^ Press Releases: January, 2007 | Electronic Frontier Foundation
43.^ MSN.com Lilly settles Zyprexa suit for $1.42 billion. The Associated Press, January 15, 2009
44.^ Cronin Fisk, Martha, Lopatto, Elizabeth and Feeley, Jef (June 1, 2009). "Lilly Sold Drug for
Dementia Knowing It Didn’t Help, Files Show". Bloomberg L.P..
http://www.bloomberg.com/apps/news?pid=20601109&sid=aTLcF3zT1Pdo. Retrieved 2009-09-
03.
45.^ Berenson, Alex (December 18, 2006). "Drug Files Show Maker Promoted Unapproved Use".
The New York Times. http://www.nytimes.com/2006/12/18/business/18drug.ht. Retrieved 2009-
09-03.
46.^ Frontal21.ZDF.de, Tödliche Nebenwirkungen? - Umstrittenes Medikament bringt satte
Gewinne
47.^ YouTube.com, Zyprexa - Umstrittenes Medikament bringt satte Gewinne

[edit] External links

[edit] Manufacturer site
• Zyprexa.com - official Zyprexa brand website from Eli Lilly
• Zyprexa package insert
[edit] Consumer information
• MedLibrary.org - 'Information on Zyprexa and How to Use It, Precautions and Other
Medications to Avoid While Taking, MedLibrary
• NIH.gov - 'Olanzapine (Systemic)' Drug Information, MedlinePlus
[edit] Controversy
 • nytyimes.com - Lilly Settles With 18,000 Over Zyprexa, Alex Berenson, New York
Times (December 17, 2006)
[show]
v•d•e
Antipsychotics/Neuroleptics (N05A)

Benzamides: Levosulpiride • Nemonapride • Sulpiride • Sultopride • Tiapride •

Veralipride; Butyrophenones: Azaperone • Benperidol • Bromperidol • Droperidol •
Fluanisone • Haloperidol • Lenperone • Moperone • Pipamperone • Spiperone •
Trifluperidol; Diphenylbutylpiperidines: Clopimozide • Fluspirilene • Penfluridol •
T
Pimozide; Phenothiazines: Acepromazine • Acetophenazine • Butaperazine •
y
Carphenazine • Chloracizine • Chlorproethazine • Chlorpromazine • Cyamemazine •
p
Dixyrazine • Fluacizine • Fluphenazine • Levomepromazine/Methotrimeprazine •
i
Mesoridazine • Perazine • Periciazine • Perphenazine • Piperacetazine • Pipotiazine •
c
Prochlorperazine • Promazine • Promethazine • Propiomazine • Sulforidazine •
a
Thiethylperazine • Thiopropazate • Thioproperazine • Thioridazine • Trifluoperazine •
l
Triflupromazine; Thioxanthenes: Chlorprothixene • Clopenthixol • Flupentixol •
Thiothixene • Zuclopenthixol; Tricyclics: Amoxapine • Butaclamol • Carpipramine •
Clocapramine • Fluotracen • Loxapine • Metitepine/Methiothepin • Octoclothiepin •
Trimipramine; Others: Prothipendyl

A Benzamides: Amisulpride • Remoxipride; Butyrophenones: Cinuperone • Setoperone;

t Benzo(iso)oxazolepiperidines: Iloperidone • Ocaperidone • Paliperidone • Risperidone;
y Benzo(iso)thiazolepiperazines: Lurasidone • Perospirone • Revospirone • Tiospirone •
p Ziprasidone; Diphenylbutylpiperazines: Amperozide; Phenylpiperazines: Aripiprazole •
i Bifeprunox • Elopiprazole • Umespirone; Tricyclics: Asenapine • Clotiapine • Clozapine •
c Fluperlapine • Gevotroline • Metitepine/Methiothepin • Mosapramine • NDMC •
a Olanzapine • Piquindone • Quetiapine • Tenilapine • Zotepine; Others: Blonanserin •
l Cariprazine • Molindone • Pimavanserin • Roxindole • Sarizotan • Sertindole • Spiramide

O
t
h Azacyclonol • Cannabidiol • D-Cycloserine • Lithium • Mifepristone • Oxypertine •
e Reserpine • Rimcazole • Secretin • Talnetant • Tetrabenazine • Vabicaserin
r
s
#
WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III
M: PSO/PSI mepr dsrd (o, p, m, p, a, d, proc,
s), sysi/epon, spvo drug(N5A/5B/5C/6A/6B/6D)

[show]
v•d•e
Cholinergics

R mAChAgonists: 77-LH-28-1 • AC-42 • AC-260,584 • Aceclidine • Acetylcholine • AF30

e
c • AF150(S) • AF267B • AFDX-384 • Alvameline • AQRA-741 • Arecoline •
e Bethanechol • Butyrylcholine • Carbachol • CDD-0034 • CDD-0078 • CDD-0097
p • CDD-0098 • CDD-0102 • Cevimeline • cis-Dioxolane • Ethoxysebacylcholine •
t LY-593,039 • L-689,660 • LY-2,033,298 • McNA343 • Methacholine •
o Milameline • Muscarine • NGX-267 • Ocvimeline • Oxotremorine • PD-151,832 •
r Pilocarpine • RS86 • Sabcomeline • SDZ 210-086 • Sebacylcholine •
Suberylcholine • Talsaclidine • Thiopilocarpine • Vedaclidine • VU-0029767 •
L VU-0090157 • VU-0152099 • VU-0152100 • VU-0238429 • WAY-132,983 •
i Xanomeline • YM-796
g Antagonists: 3-Quinuclidinyl Benzilate • 4-DAMP • Aclidinium Bromide •
a Anisodamine • Anisodine • Atropine • Atropine Methonitrate • Benactyzine •
n Benzatropine (Benztropine) • Benzydamine • BIBN 99 • Biperiden • Bornaprine •
d CAR-226,086 • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 •
s CAR-302,537 • CAR-302,668 • CS-27349 • Cyclobenzaprine • Cyclopentolate •
Darifenacin • DAU-5884 • Dimethindene • Dexetimide • DIBD • Dicyclomine
(Dicycloverine) • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • Elemicin •
R
Etanautine • Etybenzatropine (Ethylbenztropine) • Flavoxate • Himbacine • HL-
031,120 • Ipratropium • J-104,129 • Hyoscyamine • Mamba Toxin 3 • Mamba
Toxin 7 • Mazaticol • Mebeverine • Methoctramine • Metixene • Myristicin • N-
Ethyl-3-Piperidyl Benzilate • N-Methyl-3-Piperidyl Benzilate • Orphenadrine •
Otenzepad • Oxybutynin • PBID • PD-102,807 • Phenglutarimide •
Phenyltoloxamine • Pirenzepine • Piroheptine • Procyclidine • Profenamine • RU-
47,213 • SCH-57,790 • SCH-72,788 • SCH-217,443 • Scopolamine (Hyoscine) •
Solifenacin • Telenzepine • Tiotropium • Tolterodine • Trihexyphenidyl •
Tripitamine • Tropatepine • Tropicamide • WIN-2299 • Zamifenacin; Others: 1st
Generation Antihistamines (Brompheniramine, Chlorpheniramine,
Cyproheptadine, Dimenhydrinate, Diphenhydramine, Doxylamine,
Mepyramine/Pyrilamine, Phenindamine, Pheniramine, Tripelennamine,
Triprolidine, etc) • Tricyclic Antidepressants (Amitriptyline, Doxepin,
Trimipramine, etc) • Tetracyclic Antidepressants (Amoxapine, Maprotiline, etc) •
Typical Antipsychotics (Chlorpromazine, Thioridazine, etc) • Atypical
Antipsychotics (Clozapine, Olanzapine, Quetiapine, etc)

nAChRAgonists: 5-HIAA • A-84,543 • A-366,833 • A-582,941 • A-867,744 • ABT-202 •

ABT-418 • ABT-560 • ABT-894 • Acetylcholine • Altinicline • Anabasine • AR-
R17779 • Butyrylcholine • Carbachol • Cotinine • Cytisine • Decamethonium •
Desformylflustrabromine • Dianicline • Dimethylphenylpiperazinium •
Epibatidine • Epiboxidine • Ethanol • Ethoxysebacylcholine • EVP-4473 • EVP-
6124 • Galantamine • GTS-21 • Ispronicline • Lobeline • MEM-63,908 (RG-3487)
• Nicotine • NS-1738 • PHA-543,613 • PHA-709,829 • PNU-120,596 • PNU-
282,987 • Pozanicline • Rivanicline • Sazetidine A • Sebacylcholine • SIB-1508Y
• SIB-1553A • SSR-180,711 • Suberylcholine • TC-1698 • TC-1734 • TC-1827 •
TC-2216 • TC-5214 • TC-5619 • TC-6683 • Tebanicline • Tropisetron • UB-165 •
Varenicline • WAY-317,538 • XY-4083
Antagonists: 18-Methoxycoronaridine • α-Bungarotoxin • α-Conotoxin •
Alcuronium • Amantadine • Anatruxonium • Atracurium • Bupropion
(Amfebutamone) • Chandonium • Chlorisondamine • Cisatracurium • Coclaurine •
Coronaridine • Dacuronium • Decamethonium • Dextromethorphan •
 Dextropropoxyphene • Dextrorphan • Diadonium • DHβE • Dimethyltubocurarine
(Metocurine) • Dipyrandium • Dizocilpine (MK-801) • Doxacurium • Duador •
Esketamine • Fazadinium • Gallamine • Hexafluronium • Hexamethonium
(Benzohexonium) • Ibogaine • Isoflurane • Ketamine • Kynurenic Acid •
Laudexium (Laudolissin) • Levacetylmethadol • Malouetine • Mecamylamine •
Memantine • Methadone • Methorphan (Racemethorphan) • Methyllycaconitine •
Metocurine • Mivacurium • Morphanol (Racemorphanol) • Neramexane • Nitrous
Oxide • Pancuronium • Pempidine • Pentamine • Pentolinium • Phencyclidine •
Pipecuronium • Radafaxine • Rapacuronium • Rocuronium • Surugatoxin •
Suxamethonium (Succinylcholine) • Thiocolchicoside • Toxiferine • Trimethaphan
• Tropeinium • Tubocurarine • Vecuronium • Xenon

R PlasmalemmaCHT InhibitorsHemicholinium-3 (Hemicholine)

e l
u
p VesicularVAChT InhibitorsVesamicol
t
a
k
e

I
n
h
i
b
i
t
o
r
s

E 1-(-Benzoylethyl)pyridinium • 2-(α-
n Naphthoyl)ethyltrimethylammonium • 3-Chloro-4-stillbazole
z • 4-(1-Naphthylvinyl)pyridine • Acetylseco Hemicholinium-
y AnabolismChAT Inhibitors3 • Acryloylcholine • AF64A • B115 • BETA • CM-54,903 •
m N,N-Dimethylaminoethylacrylate • N,N-
e Dimethylaminoethylchloroacetate
I CatabolisAChE InhibitorsReversible: Carbamates: Aldicarb • Bendiocarb • Bufencarb
n m • Carbaryl • Carbendazim • Carbetamide • Carbofuran •
h Chlorbufam • Chloropropham • Ethienocarb • Ethiofencarb •
i Fenobucarb • Fenoxycarb • Formetanate • Furadan •
b Ladostigil • Methiocarb • Methomyl • Miotine • Oxamyl •
i Phenmedipham • Pinmicarb • Pirimicarb • Propamocarb •
t Propham • Propoxur; Stigmines: Ganstigmine • Neostigmine
o • Phenserine • Physostigmine • Pyridostigmine •
r
 Rivastigmine; Others: Acotiamide • Ambenonium •
Donepezil • Edrophonium • Galantamine • Huperzine A •
Minaprine • Tacrine • Zanapezil
Irreversible: Organophosphates: Acephate • Azinphos-
Methyl • Bensulide • Cadusafos • Chlorethoxyfos •
Chlorfenvinphos • Chlorpyrifos • Chlorpyrifos-Methyl •
Coumaphos • Cyclosarin (GF) • Demeton • Demeton-S-
Methyl • Diazinon • Dichlorvos • Dicrotophos • Diisopropyl
Fluorophosphate (Guthion) • Diisopropylphosphate •
Dimethoate • Dioxathion • Disulfoton • EA-3148 •
Echothiophate • Ethion • Ethoprop • Fenamiphos •
s Fenitrothion • Fenthion • Fosthiazate • GV • Isofluorophate •
Isoxathion • Malaoxon • Malathion • Methamidophos •
Methidathion • Metrifonate • Mevinphos • Monocrotophos •
Naled • Novichok Agent • Omethoate • Oxydemeton-Methyl
• Paraoxon • Parathion • Parathion-Methyl • Phorate •
Phosalone • Phosmet • Phostebupirim • Phoxim • Pirimiphos-
Methyl • Sarin (GB) • Soman (GD) • Tabun (GA) • Temefos
• Terbufos • Tetrachlorvinphos • Tribufos • Trichlorfon • VE
• VG • VM • VR • VX; Others: Demecarium • Onchidal
(Onchidella Binneyi)

* Many of the acetylcholinesterase inhibitors listed above act as

BChE Inhibitorsbutyrylcholinesterase inhibitors.

Choline (Lecithin) • Citicoline • Cyprodenate • Dimethylethanolamine (DMAE;

PrecursorDeanol) • Glycerophosphocholine • Meclofenoxate (Centrophenoxine) •
sPhosphatidylcholine • Phosphatidylethanolamine • Phosphorylcholine •
O Pirisudanol
t
h
Acetic Acid • Acetyl-L-Carnitine • Acetyl-Coenzyme A • Vitamin B5
e Cofactors
(Pantothenic Acid, Pantethine, Pantetheine, Panthenol)
r
s
Acetylcholine Releasing Agents: α-Latrotoxin • β-Bungarotoxin; Acetylcholine
OthersRelease Inhibitors: Botulinum Toxin (Botox); Acetylcholinesterase
Reactivators: Pralidoxime • obidoxime

[show]
v•d•e
Dopaminergics

R AgonistsAdamantanes: Amantadine • Memantine • Rimantadine; Aminotetralins: 7-

e OH-DPAT • 8-OH-PBZI • Rotigotine • UH-232; Benzazepines: 6-Br-APB •
c Fenoldopam • SKF-38,393 • SKF-77,434 • SKF-81,297 • SKF-82,958 • SKF-
e 83,959; Ergolines: Bromocriptine • Cabergoline • Dihydroergocryptine •
p Lisuride • LSD • Pergolide; Dihydrexidine-derivatives: 2-OH-NPA • A-86,929
t • Ciladopa • Dihydrexidine • Dinapsoline • Dinoxyline • Doxanthrine; Others:
 A-68,930 • A-77,636 • A-412,997 • ABT-670 • ABT-724 • Aplindore •
Apomorphine • Aripiprazole • Bifeprunox • BP-897 • CY-208,243 •
Dizocilpine • Etilevodopa • Flibanserin • Ketamine • Melevodopa • Modafinil
• Pardoprunox • Phencyclidine • PD-128,907 • PD-168,077 • PF-219,061 •
Piribedil • Pramipexole • Propylnorapomorphine • Pukateine • Quinagolide •
Quinelorane • Quinpirole • RDS-127 • Ro10-5824 • Ropinirole • Rotigotine •
Roxindole • Salvinorin A • SKF-89,145 • Sumanirole • Terguride •
Umespirone • WAY-100,635
o
Typical Antipsychotics: Acepromazine • Azaperone • Benperidol •
r
Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol
• Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine •
L
Mesoridazine • Methotrimeprazine • Nemonapride • Penfluridol • Perazine •
i
Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine •
g
Sulforidazine • Sulpiride • Sultopride • Thioridazine • Thiothixene •
a
Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; Atypical
n
Antipsychotics: Amisulpride • Asenapine • Blonanserin • Clozapine •
d
AntagonistGevotroline • Iloperidone • Lurasidone • Melperone • Molindone •
s
sMosapramine • Ocaperidone • Olanzapine • Paliperidone • Perospirone •
Piquindone • Quetiapine • Remoxipride • Risperidone • Sertindole • Tiospirone
• Ziprasidone • Zotepine; Antiemetics: AS-8112 • Alizapride • Bromopride •
Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others:
Amoxapine • Buspirone • Butaclamol • Ecopipam • EEDQ • Eticlopride •
Fananserin • L-745,870 • Nafadotride • Nuciferine • PNU-99,194 • Raclopride
• Sarizotan • SB-277,011-A • SCH-23,390 • SKF-83,566 • SKF-83,959 •
Sonepiprazole • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine
• Tiapride • UH-232 • Yohimbine

R PlasmalemmaDAT InhibitorsPiperazines: DBL-583 • GBR-12,935 • Nefazodone •

e l Vanoxerine; Piperidines: BTCP • Desoxypipradrol •
u Dextromethylphenidate • Difemetorex • Ethylphenidate •
p Methylnaphthidate • Methylphenidate • Phencyclidine •
t Pipradrol; Pyrrolidines: Diphenylprolinol •
a Methylenedioxypyrovalerone (MDPV) • Naphyrone •
k Prolintane • Pyrovalerone; Tropanes: β-CPPIT • Altropane
e • Brasofensine • CFT • Cocaine • Dichloropane •
Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (123I)
I • Iometopane • RTI-112 • RTI-113 • RTI-121 • RTI-126 •
n RTI-150 • RTI-177 • RTI-229 • RTI-336 • Tenocyclidine •
h Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 •
i WF-31 • WF-33; Others: Adrafinil • Armodafinil •
b Amfonelic Acid • Amineptine • Benzatropine
i (Benztropine) • Bromantane • BTQ • BTS-74,398 •
t Bupropion (Amfebutamone) • Ciclazindol • Diclofensine •
o Dimethocaine • Diphenylpyraline • Dizocilpine • DOV-
r 102,677 • DOV-21,947 • DOV-216,303 • Etybenzatropine
s (Ethylbenztropine) • EXP-561 • Fencamine •
 Fencamfamine • Fezolamine • GYKI-52,895 • Indatraline •
Ketamine • Lefetamine • Levophacetoperane • LR-5182 •
Manifaxine • Mazindol • Medifoxamine • Mesocarb •
Modafinil • Nefopam • Nomifensine • NS-2359 • O-2172 •
Pridefrine • Propylamphetamine • Radafaxine • SEP-
225,289 • SEP-227,162 • Sibutramine • Tametraline •
Tripelennamine

VesicularVMAT InhibitorsDeserpidine • Ibogaine • Reserpine • Tetrabenazine

R Morpholines: Fenbutrazate • Morazone • Phendimetrazine • Phenmetrazine; Oxazolines: 4-

e Methylaminorex (4-MAR, 4-MAX) • Aminorex • Clominorex • Cyclazodone • Fenozolone
l • Fluminorex • Pemoline • Thozalinone; Phenethylamines (also Amphetamines, Cathinones,
e Phentermines, etc): 2-Hydroxyphenethylamine (2-OH-PEA) • 4-CAB • 4-
a Methylamphetamine (4-MA) • 4-Methylmethamphetamine (4-MMA) • Alfetamine •
s Amfecloral • Amfepentorex • Amfepramone • Amphetamine (Dextroamphetamine,
i Levoamphetamine) • Amphetaminil • β-Methylphenethylamine (β-Me-PEA) •
n Benzodioxolylbutanamine (BDB) • Benzodioxolylhydroxybutanamine (BOH) •
g Benzphetamine • Buphedrone • Butylone • Cathine • Cathinone • Clobenzorex •
Clortermine • D-Deprenyl • Dimethoxyamphetamine (DMA) •
A Dimethoxymethamphetamine (DMMA) • Dimethylamphetamine • Dimethylcathinone
g (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Ethylamphetamine •
e Ethylbenzodioxolylbutanamine (EBDB) • Ethylone • Fenethylline • Fenproporex •
n Flephedrone • Fludorex • Furfenorex • Hordenine • Lophophine (Homomyristicylamine) •
t Mefenorex • Mephedrone • Methamphetamine (Desoxyephedrine, Methedrine;
s Dextromethamphetamine, Levomethamphetamine) • Methcathinone (Methylpropion) •
Methedrone • Methoxymethylenedioxyamphetamine (MMDA) •
Methoxymethylenedioxymethamphetamine (MMDMA) • Methylbenzodioxolylbutanamine
(MBDB) • Methylenedioxyamphetamine (MDA; Tenamfetamine) •
Methylenedioxyethylamphetamine (MDEA) • Methylenedioxyhydroxyamphetamine
(MDOH) • Methylenedioxymethamphetamine (MDMA) •
Methylenedioxymethylphenethylamine (MDMPEA; Homarylamine) •
Methylenedioxyphenethylamine (MDPEA; Homopiperonylamine) • Methylone •
Ortetamine • Parabromoamphetamine (PBA) • Parachloroamphetamine (PCA) •
Parafluoroamphetamine (PFA) • Parafluoromethamphetamine (PFMA) •
Parahydroxyamphetamine (PHA) • Paraiodoamphetamine (PIA) • Paredrine
(Norpholedrine, Oxamphetamine) • Phenethylamine (PEA) • Pholedrine •
Phenpromethamine • Prenylamine • Propylamphetamine • Tiflorex (Flutiorex) • Tyramine
(TRA) • Xylopropamine • Zylofuramine; Piperazines: 2,5-Dimethoxy-4-
bromobenzylpiperazine (2C-B-BZP) • Benzylpiperazine (BZP) • Methoxyphenylpiperazine
(MeOPP; Paraperazine) • Methylbenzylpiperazine (MBZP) •
Methylenedioxybenzylpiperazine (MDBZP; Piperonylpiperazine); Others: 2-Amino-1,2-
dihydronaphthalene (2-ADN) • 2-Aminoindane (2-AI) • 2-Aminotetralin (2-AT) • 4-
Benzylpiperidine (4-BP) • 5-IAI • Clofenciclan • Cyclopentamine • Cypenamine •
Cyprodenate • Feprosidnine • Gilutensin • Heptaminol • Hexacyclonate •
Indanylaminopropane (IAP) • Indanorex • Isometheptene • Methylhexanamine •
Naphthylaminopropane (NAP) • Octodrine • Phthalimidopropiophenone • Propylhexedrine
 (Levopropylhexedrine) • Tuaminoheptane (Tuamine)

PAH Inhibitors3,4-Dihydroxystyrene

3-Iodotyrosine • Aquayamycin • Bulbocapnine •

Anabolism TH Inhibitors
Metirosine • Oudenone

AAAD / DDC InhibitorsBenserazide • Carbidopa • Genistein • Methyldopa

E
n
z Nonselective: Benmoxin • Caroxazone • Echinopsidine •
y Furazolidone • Hydralazine • Indantadol • Iproclozide •
m Iproniazid • Isocarboxazid • Isoniazid • Linezolid •
e Mebanazine • Metfendrazine • Nialamide • Octamoxin •
Paraxazone • Phenelzine • Pheniprazine • Phenoxypropazine
I • Pivalylbenzhydrazine • Procarbazine • Safrazine •
n Tranylcypromine; MAO-A Selective: Amiflamine •
h Bazinaprine • Befloxatone • Befol • Brofaromine •
MAO Inhibitors
i Cimoxatone • Clorgiline • Esuprone • Harmala alkaloids
b (Harmine, Harmaline, Tetrahydroharmine, Harman,
Catabolis Norharman, etc) • Methylene Blue • Metralindole •
i m
t Minaprine • Moclobemide • Pirlindole • Sercloremine •
o Tetrindole • Toloxatone • Tyrima; MAO-B Selective: D-
r Deprenyl • L-Deprenyl (Selegiline) • Ladostigil •
s Lazabemide • Milacemide • Mofegiline • Pargyline •
Rasagiline

COMT InhibitorsEntacapone • Tolcapone

Bupicomide • Disulfiram • Dopastin • Fusaric Acid •

DBH Inhibitors
Nepicastat • Phenopicolinic Acid • Tropolone

Precursor
L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa)
s
O
Ferrous Iron (Fe2+) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide
t
→ NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal
h Cofactors
Phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic Acid) • Vitamin C
e
(Ascorbic Acid) • Zinc (Zn2+)
r
s
Activity Enhancers: Benzofuranylpropylaminopentane (BPAP) •
OthersPhenylpropylaminopentane (PPAP); Toxins: Oxidopamine (6-
Hydroxydopamine)

[show]
v•d•e
Histaminergics
 Agonists: 2-Pyridylethylamine • Betahistine • Histamine • HTMT • UR-AK49
Antagonists: 1st Generation: 4-Methyldiphenhydramine • Alimemazine • Antazoline •
Azatadine • Bamipine • Benzatropine (Benztropine) • Bepotastine • Bromazine •
Brompheniramine • Buclizine • Captodiame • Carbinoxamine • Chlorcyclizine •
Chloropyramine • Chlorothen • Chlorpheniramine • Chlorphenoxamine • Cinnarizine •
Clemastine • Clobenzepam • Clocinizine • Cyclizine • Cyproheptadine • Dacemazine •
Deptropine • Dexbrompheniramine • Dexchlorpheniramine • Dimenhydrinate •
Dimetindene • Diphenhydramine • Diphenylpyraline • Doxylamine • Embramine •
Etybenzatropine (Ethylbenztropine) • Etymemazine • Histapyrrodine •
Homochlorcyclizine • Hydroxyethylpromethazine • Hydroxyzine • Isopromethazine •
Isothipendyl • Meclizine • Mepyramine (Pyrilamine) • Mequitazine • Methafurylene •
Methapyrilene • Methdilazine • Moxastine • Niaprazine • Orphenadrine • Oxatomide •
R H1Oxomemazine • Phenindamine • Pheniramine • Phenyltoloxamine • Pimethixene •
e Piperoxan • Promethazine • Propiomazine • Pyrrobutamine • Talastine • Thenalidine •
c Thenyldiamine • Thiazinamium • Thonzylamine • Tolpropamine • Tripelennamine •
e Triprolidine; 2nd Generation: Acrivastine • Astemizole • Azelastine • Cetirizine •
p Clemizole • Clobenztropine • Ebastine • Emedastine • Epinastine • Ketotifen •
t Latrepirdine • Levocabastine • Loratadine • Mebhydrolin • Mizolastine • Olopatadine •
o Rupatadine • Setastine • Terfenadine; 3rd Generation: Desloratadine • Fexofenadine •
r Levocetirizine; Miscellaneous: Tricyclic Antidepressants (Amitriptyline, Doxepin,
Trimipramine, etc) • Tetracyclic Antidepressants (Mianserin, Mirtazapine, etc) •
L Serotonin Antagonists and Reuptake Inhibitors (Trazodone, Nefazodone) • Typical
i Antipsychotics (Chlorpromazine, Thioridazine, etc) • Atypical Antipsychotics
g (Clozapine, Olanzapine, Quetiapine, etc)
a
n
Agonists: Amthamine • Betazole • Dimaprit • Histamine • HTMT • Impromidine • UR-
d
AK49
s H2
Antagonists: Cimetidine • Famotidine • Lafutidine • Lavoltidine • Metiamide •
Niperotidine • Nizatidine • Ranitidine • Roxatidine

Agonists: α-Methylhistamine • Cipralisant • Histamine • Imetit • Immepip •

Immethridine • Methimepip • Proxyfan
Antagonists: A-349,821 • A-423,579 • ABT-239 • Betahistine • Burimamide •
H3
Ciproxifan • Clobenpropit • Conessine • GSK-189,254 • Impentamine • Iodophenpropit •
JNJ-5,207,852 • MK-0249 • NNC-38-1,049 • PF-03654746 • SCH-79,687 •
Thioperamide • Tiprolisant • VUF-5,681

Agonists: 4-Methylhistamine • Histamine • VUF-8,430

H4
Antagonists: JNJ-7,777,120 • Thioperamide • VUF-6,002

R Plasmalemma
e .....
l
u
p VesicularVMAT InhibitorsIbogaine • Reserpine • Tetrabenazine
t
a
k
e

I
n
h
i
b
i
t
o
r
s

E α-FMH • Brocresine • Catechin • Cyanidanol-3 • McN-A-

n AnabolismHDC Inhibitors1293 • ME • Meciadanol • Naringenin • Thiazol-4-
z yimethoxyamine • Tritoqualine • Zy-15,029
y
m Amodiaquine • BW-301U • Diphenhydramine • Harmaline •
e CatabolisHNMT InhibitorsMetoprine • Quinacrine • SKF-91,488 • Tacrine
m
I DAO Inhibitors1,4-Diamino-2-butyne • Aminoguanidine
n
h
i
b
i
t
o
r
s

O Precursor
t L-Histidine
s
h
e CofactorsVitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate)
r
s

[show]
v•d•e
Serotonergics

R Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Enilospirone •

e Eptapirone • Gepirone • Ipsapirone • Perospirone • Revospirone • Tandospirone •
c 5-HT1ATiospirone • Umespirone • Zalospirone; Antidepressants: Etoperidone •
e Nefazodone • Trazodone; Antipsychotics: Aripiprazole • Asenapine • Clozapine •
p Quetiapine • Ziprasidone; Ergolines: Dihydroergotamine • Ergotamine • Lisuride •
t
 Methysergide • LSD; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • Bufotenin •
DMT • Psilocin • Psilocybin; Others: 8-OH-DPAT • Adatanserin • Befiradol •
BMY-14802 • Dimemebfe • Ebalzotan • Eltoprazine • F-11,461 • F-12,826 • F-
13,714 • F-14,679 • F-15,063 • F-15,599 • Flesinoxan • Flibanserin • Lesopitron •
Lu AA21004 • LY-293,284 • LY-301,317 • MKC-242 • NBUMP • Osemozotan •
Oxaflozane • Pardoprunox • Piclozotan • Rauwolscine • Repinotan • Roxindole •
RU-24969 • S-15535 • Sarizotan • SSR-181,507 • Sunepitron • U-92016A •
Urapidil • Vilazodone • Xaliproden • Yohimbine
Antagonists: Antipsychotics: Iloperidone • Risperidone • Sertindole; Beta Blockers:
Alprenolol • Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind •
Pindolol • Propranolol • Tertatolol; Others: AV965 • BMY-7378 • Dotarizine •
Flopropione • GR-46611 • Isamoltane • Lecozotan • Metitepine/Methiothepin •
MPPF • NAN-190 • PRX-00023 • Robalzotan • S-15535 • SB-649915 • SDZ 216-
525 • Spiperone • Spiramide • Spiroxatrine • UH-301 • WAY-100,135 • WAY-
100,635 • Xylamidine

Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Methysergide;

Piperazines: Eltoprazine • TFMPP; Triptans: Avitriptan • Eletriptan • Sumatriptan •
Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CGS-12066A • CP-93,129 • CP-
o 5-HT 94,253 • CP-135,807 • RU-24969
1B
r Antagonists: Lysergamides: Metergoline; Others: AR-A000002 • Elzasonan • GR-
127,935 • Isamoltane • Metitepine/Methiothepin • SB-216,641 • SB-224,289 • SB-
l 236,057 • Yohimbine
i
g
Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans:
a
Almotriptan • Avitriptan • Eletriptan • Frovatriptan • Naratriptan • Rizatriptan •
n
Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CP-135,807 • CP-
d
5-HT1D286,601 • GR-46611 • L-694,247 • L-772,405 • PNU-109,291 • PNU-142,633
s
Antagonists: Lysergamides: Metergoline; Others: Alniditan • BRL-15572 •
Elzasonan • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 •
LY-456,220 • Metitepine/Methiothepin • Ritanserin • Yohimbine • Ziprasidone

Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-

5-HT1E54443 • Tryptamine
Antagonists: Metitepine/Methiothepin

Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT;

5-HT1FOthers: BRL-54443 • LY-334,370
Antagonists: Metitepine/Methiothepin

5-HT2AAgonists: Lysergamides: ALD-52 • Ergonovine • Lisuride • LA-SS-Az • LSD •

LSD-Pip • Lysergic acid 2-butyl amide • Methysergide; Phenethylamines: 25I-
NBMD • 25I-NBOH • 25I-NBOMe • 2C-B • 2C-B-FLY • 2CB-Ind • 2C-E • 2C-I •
2C-T-2 • 2C-T-7 • 2C-T-21 • 2CBCB-NBOMe • 2CBFly-NBOMe • Bromo-
DragonFLY • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • TCB-2 •
TFMFly; Piperazines: BZP • Quipazine • TFMPP; Tryptamines: 5-CT • 5-MeO-α-
ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT •
 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT •
Psilocin • Psilocybin; Others: AL-34662 • AL-37350A • Dimemebfe •
Medifoxamine • Oxaflozane • PNU-22394 • RH-34
Antagonists: Atypical Antipsychotics: Amperozide • Aripiprazole • Clozapine •
Gevotroline • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide •
Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical
Antipsychotics: Loxapine • Pipamperone; Antidepressants: Amitriptyline •
Amoxapine • Etoperidone • Mianserin • Mirtazapine • Nefazodone • Trazodone;
Others: 5-I-R91150 • AC-90179 • Adatanserin • Altanserin • AMDA • APD-215 •
Blonanserin • Cinanserin • Cyproheptadine • Deramciclane • Dotarizine •
Eplivanserin • Esmirtazapine • Fananserin • Flibanserin • Ketanserin • KML-010 •
Lubazodone • Mepiprazole • Metitepine/Methiothepin • Nantenine • Pimavanserin •
Pizotifen • Pruvanserin • Rauwolscine • Ritanserin • Sarpogrelate • Setoperone •
Spiperone • Spiramide • SR-46349B • Volinanserin • Xylamidine • Yohimbine

Agonists: Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines:

Chlorphentermine • Cloforex • DOB • DOC • DOI • DOM • Fenfluramine • MDA •
MDMA • Norfenfluramine; Tryptamines: 5-CT • 5-MT • α-Methyl-5-HT; Others:
BW-723C86 • Cabergoline • mCPP • Pergolide • PNU-22394 • Ro60-0175
5-HT2B
Antagonists: Agomelatine • Asenapine • EGIS-7625 • Ketanserin • Lisuride • LY-
272,015 • Metitepine/Methiothepin • Rauwolscine • Ritanserin • RS-127,445 •
Sarpogrelate • SB-200,646 • SB-204,741 • SB-206,553 • SB-215,505 • SB-
221,284 • SB-228,357 • SDZ SER-082 • Tegaserod • Yohimbine

Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 •

DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline; Piperazines:
Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-
MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET •
α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin •
Psilocybin; Others: A-372,159 • AL-38022A • CP-809,101 • Dimemebfe •
Lorcaserin• Medifoxamine • MK-212 • ORG-37,684 • Oxaflozane • PNU-22394 •
Ro60-0175 • Vabicaserin • WAY-629 • WAY-161,503 • YM-348
Antagonists: Atypical Antipsychotics: Clozapine • Iloperidone • Melperone •
5-HT2C
Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole •
Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine •
Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine •
Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Nortriptyline •
Trazodone; Others: Adatanserin • Cinanserin • Cyproheptadine • Deramciclane •
Dotarizine • Eltoprazine • Esmirtazapine • FR-260,010 • Ketanserin • Ketotifen •
Latrepirdine • Lu AA24530 • Metitepine/Methiothepin • Methysergide • Pizotifen •
Ritanserin • RS-102,221 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 •
SB-242,084 • SB-243,213 • SDZ SER-082 • Xylamidine

Agonists: Piperazines: BZP • Quipazine; Tryptamines: 2-Methyl-5-HT • 5-CT;

Others: Chlorophenylbiguanide • Butanol • Ethanol • Halothane • Isoflurane • RS-
5-HT356812 • SR-57,227 • SR-57,227-A • Toluene • Trichloroethane • Trichloroethanol •
Trichloroethylene • YM-31636
Antagonists: Antiemetics: AS-8112 • Alosetron • Azasetron • Batanopride •
 Bemesetron • Cilansetron • Dazopride • Dolasetron • Granisetron • Lerisetron •
Ondansetron • Palonosetron • Ramosetron • Renzapride • Tropisetron • Zacopride •
Zatosetron; Atypical Antipsychotics: Clozapine • Olanzapine • Quetiapine;
Tetracyclic Antidepressants: Amoxapine • Mianserin • Mirtazapine; Others: ICS-
205,930 • Lu AA21004 • Lu AA24530 • MDL-72,222 • Memantine • Nitrous
Oxide • Ricasetron • Sevoflurane • Thujone • Xenon

Agonists: Gastroprokinetic Agents: Cinitapride • Cisapride • Dazopride •

Metoclopramide • Mosapride • Prucalopride • Renzapride • Tegaserod • Zacopride;
Others: 5-MT • BIMU-8 • CJ-033,466 • PRX-03140 • RS-67333 • RS-67506 •
5-HT4
SL65.0155 • TD-5108
Antagonists: GR-113,808 • GR-125,487 • L-Lysine • Piboserod • RS-39604 • RS-
67532 • SB-203,186

Agonists: Lysergamides: Ergotamine • LSD; Tryptamines: 5-CT; Others: Valerenic

Acid
5-HT5AAntagonists: Asenapine • Latrepirdine • Metitepine/Methiothepin • Ritanserin •
SB-699,551
* Note that the 5-HT5B receptor is not functional in humans.

Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Lisuride • LSD •

Mesulergine • Metergoline • Methysergide; Tryptamines: 2-Methyl-5-HT • 5-BT •
5-CT • 5-MT • Bufotenin • E-6801 • E-6837 • EMD-386,088 • EMDT • LY-
586,713 • N-Methyl-5-HT • Tryptamine; Others: WAY-181,187 • WAY-208,466
Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine •
Doxepin • Mianserin • Nortriptyline; Atypical Antipsychotics: Aripiprazole •
5-HT6
Asenapine • Clozapine • Fluperlapine • Iloperidone • Olanzapine • Tiospirone;
Typical Antipsychotics: Chlorpromazine • Loxapine; Others: BGC20-760 • BVT-
5182 • BVT-74316 • EGIS-12233 • GW-742,457 • Ketanserin • Latrepirdine • Lu
AE58054 • Metitepine/Methiothepin • MS-245 • PRX-07034 • Ritanserin • Ro 04-
6790 • Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 • SB-
742,457

Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT • Bufotenin; Others: 8-

OH-DPAT • AS-19 • Bifeprunox • LP-12 • LP-44 • RU-24,969 • Sarizotan
Antagonists: Lysergamides: 2-Bromo-LSD • Bromocriptine • Dihydroergotamine •
Ergotamine • Mesulergine • Metergoline • Methysergide; Antidepressants:
Amitriptyline • Amoxapine • Clomipramine • Imipramine • Maprotiline •
5-HT7Mianserin; Atypical Antipsychotics: Amisulpride • Aripiprazole • Clozapine •
Olanzapine • Risperidone • Sertindole • Tiospirone • Ziprasidone • Zotepine;
Typical Antipsychotics: Chlorpromazine • Loxapine; Others: Butaclamol • EGIS-
12233 • Ketanserin • LY-215,840 • Metitepine/Methiothepin • Pimozide •
Ritanserin • SB-258,719 • SB-258,741 • SB-269,970 • SB-656,104 • SB-656,104-
A • SB-691,673 • SLV-313 • SLV-314 • Spiperone • SSR-181,507

R SERTSelective Serotonin Reuptake Inhibitors (SSRIs): Alaproclate • Citalopram •

e Dapoxetine • Desmethylcitalopram • Desmethylsertraline • Escitalopram •
 Femoxetine • Fluoxetine • Fluvoxamine • Indalpine • Ifoxetine • Litoxetine • Lu
AA21004 • Lubazodone • Paroxetine • Pirandamine • RTI-353 • Seproxetine •
u
Sertraline • Vilazodone • Zimelidine; Serotonin-Norepinephrine Reuptake
p
Inhibitors (SNRIs): Bicifadine • Desvenlafaxine • Duloxetine • Levomilnacipran •
t
Milnacipran • Sibutramine • Venlafaxine; Serotonin-Norepinephrine-Dopamine
a
Reuptake Inhibitors (SNDRIs): Brasofensine • Diclofensine • DOV-102,677 •
k
DOV-21,947 • DOV-216,303 • NS-2359 • SEP-225,289 • SEP-227,162 •
e
Tesofensine; Tricyclic Antidepressants (TCAs): Amitriptyline • Butriptyline •
Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine •
I
Lofepramine • Nortriptyline • Pipofezine • Protriptyline • Trimipramine;
n
Tetracyclic Antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone •
h
Trazodone; Antihistamines: Brompheniramine • Chlorpheniramine •
i
Diphenhydramine • Mepyramine/Pyrilamine • Pheniramine • Tripelennamine;
b
Opioids: Meperidine (Pethidine) • Methadone • Propoxyphene; Others: Cocaine •
i
CP-39,332 • Cyclobenzaprine • Dextromethorphan • Dextrorphan • EXP-561 •
t
Fezolamine • Mesembrine • Nefopam • PIM-35 • Pridefrine • Roxindole • SB-
o
649,915 • Ziprasidone
r
s
VMA
Ibogaine • Reserpine • Tetrabenazine
T

R
e Aminoindanes: 5-IAI • ETAI • MDAI • MDMAI • MMAI • TAI; Aminotetralins: 6-CAT •
l 8-OH-DPAT • MDAT • MDMAT; Oxazolines: 4-Methylaminorex • Aminorex •
e Clominorex • Fluminorex; Phenethylamines (also Amphetamines, Cathinones,
a Phentermines, etc): 2-Methyl-MDA • 4-CAB • 4-FA • 4-FMA • 4-HA • 4-MTA • 5-
s APDB • 5-Methyl-MDA • 6-APDB • 6-Methyl-MDA • Amiflamine • BDB • BOH •
i Brephedrone • Butylone • Chlorphentermine • Cloforex • Diethylcathinone •
n Dimethylcathinone • DMA • DMMA • EBDB • EDMA • Ethylone • Etolorex •
g Fenfluramine (Dexfenfluramine) • Flephedrone • IAP • IMP • Lophophine • MBDB •
MDA • MDEA • MDHMA • MDMA • MDMPEA • MDOH • MDPEA • Mephedrone •
A Methedrone • Methylone • MMA • MMDA • MMDMA • NAP • Norfenfluramine • pBA •
g pCA • pIA • PMA • PMEA • PMMA • TAP; Piperazines: 2C-B-BZP • BZP • MBZP •
e mCPP • MDBZP • MeOPP • Mepiprazole • pFPP • TFMPP; Tryptamines: 4-Methyl-αET •
n 4-Methyl-αMT • 5-CT • 5-MeO-αET • 5-MeO-αMT • 5-MT • αET • αMT • DMT •
t Tryptamine (itself); Others: Indeloxazine • Tramadol • Viqualine
s

E TPHAGN-2979 • Fenclonine
n Anabolism
z AAADBenserazide • Carbidopa • Genistein • Methyldopa
y
m CatabolisMAONonselective: Benmoxin • Caroxazone • Echinopsidine • Furazolidone •
e m Hydralazine • Indantadol • Iproclozide • Iproniazid • Isocarboxazid •
Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide •
I Octamoxin • Paraxazone • Phenelzine • Pheniprazine •
n Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine •
h
i Tranylcypromine; MAO-A Selective: Amiflamine • Bazinaprine •
b Befloxatone • Befol • Brofaromine • Cimoxatone • Clorgiline •
i Esuprone • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine,
t Harman, Norharman, etc) • Methylene Blue • Metralindole • Minaprine •
o Moclobemide • Pirlindole • Sercloremine • Tetrindole • Toloxatone •
r Tyrima
s

Precursor
L-Tryptophan → 5-HTP
s
O
t
Ferrous iron (Fe2+) • Magnesium (Mg2+) • Tetrahydrobiopterin • Vitamin B3
h
(Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine,
e Cofactors
Pyridoxal → Pyridoxal phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic
r
acid) • Vitamin C (Ascorbic acid) • Zinc (Zn2+)
s
OthersActivity Enhancers: BPAP • PPAP; Reuptake Enhancers: Tianeptine

[show]
v•d•e
Piperazines

S 1-Cyclohexylpiperazine • Aminoethylpiperazine • Diethylcarbamazine • HEPPS •

i Midafotel • Piperazine • PIPES
m
p
l
e

p
i
p
e
r
a
z
i
n
e
s

(
n
o

a
d
d
i
t
i
o
n
a
l

r
i
n
g
s
)

P
h
e
n
y Acaprazine • Antrafenine • Aripiprazole • Batoprazine • Bifeprunox • BRL-15,572 •
l Ciprofloxacin • Dapiprazole • DCPP • DMPP • Dropropizine • EGIS-12,233 • Elopiprazole
p • Eltoprazine • Enpiprazole • Ensaculin • Etoperidone • Flesinoxan • Flibanserin •
i Fluprazine • Itraconazole • Ketoconazole • Levodropropizine • Lorpiprazole • mCPP •
p MeOPP • Mepiprazole • Naftopidil • Naphthylpiperazine • Nefazodone • Niaprazine •
e Oxypertine • Pardoprunox • pCPP • pFPP • Posaconazole • PRX-00023 • S-15,535 • SB-
r 258,585 • SB-271,046 • SB-357,134 • SB-399,885 • Sonepiprazole • TFMPP •
a Tolpiprazole • Trazodone • Urapidil • Vesnarinone • Vilazodone • WAY-100,135 • WAY-
z 100,635
i
n
e
s

B
e
n
z
y
l
p
i 2C-B-BZP • Befuraline • Bifeprunox • Buclizine • BZP • Chlorbenzoxamine • DBZP •
p Fipexide • Imatinib • MBZP • MDBZP • Meclizine • Piberaline • Piribedil • Trimetazidine •
e Vesnarinone
r
a
z
i
n
e
s
D Almitrine • Amperozide • BRL-15,572 • Buclizine • BW373U86 • Cetirizine •
i Chlorbenzoxamine • Chlorcyclizine • Cinnarizine • Clocinizine • Cyclizine • DBL-583 •
p Diphenylmethylpiperazine • Dotarizine • DPI-221 • DPI-287 • DPI-3290 • GBR-12,783 •
h GBR-12,935 • GBR-13,069 • GBR-13,098 • GBR-13,119 • Hydroxyzine • Lidoflazine •
e Manidipine • Meclizine • Oxatomide • SNC-80 • Vanoxerine
n
y
l
a
l
k
y
l
p
i
p
e
r
a
z
i
n
e
s

(
b
e
n
z
h
y
d
r
y
l
a
l
k
y
l
p
i
p
e
r
a
z
i
n
e
s
)

P
y
r
i
m
i
d
i
n
y
Buspirone • Dasatinib • Eptapirone • Gepirone • Ipsapirone • Piribedil •
l
Pyrimidinylpiperazine • Revospirone • Tandospirone • Tirilazad • Trimazosin •
p
Umespirone • Zalospirone
i
p
e
r
a
z
i
n
e
s

P
y
r
i
d
i
n
y
l
p
Atevirdine • Azaperone • Pyridinylpiperazine
i
p
e
r
a
z
i
n
e
s

B
Lurasidone • Perospirone • Revospirone • Tiospirone • Ziprasidone
e
n
z
o
(
i
s
o
)
t
h
i
a
z
o
l
y
l
p
i
p
e
r
a
z
i
n
e
s

T Amoxapine • Clopenthixol • Clozapine • Flupentixol • Fluphenazine • Loxapine •

r Olanzapine • Opipramol • Perazine • Perphenazine • Pirenzepine • Prochlorperazine •
i Thiethylperazine • Thiothixene • Trifluoperazine • Zuclopenthixol
c
y
c
l
i
c
s

(
p
i
p
e
r
a
z
i
n
e

a
t
t
a
c
h
e
d

v
i
a

s
i
d
e

c
h
a
i
n
)

O
t
6-Nitroquipazine • Azimilide • Cinepazet • Cyclohexylpiperazine • Hexocyclium •
h
Indinavir • JNJ-7777120 • Lodenafil • Mirodenafil • PB-28 • Quipazine • Ranolazine • SA-
e
4503 • Sildenafil • Tadalafil • Vardenafil • VUF-6002 • Zipeprol
r
s

[show]
v•d•e
Tricyclics

C
l
a Acridine • Anthracene • Dibenzazepine • Dibenzocycloheptene • Dibenzodiazepine •
s Dibenzothiazepine • Dibenzothiepin • Dibenzoxazepine • Dibenzoxepin • Phenothiazine •
s Pyridazinobenzoxazine • Pyridinobenzodiazepine • Thioxanthene
e
s

A 7-OH-Amoxapine • Amineptine • Amitriptyline • Amitriptylinoxide • Amoxapine •

n Azepindole • Butriptyline • Cianopramine • Ciclazindol • Clomipramine • Cotriptyline •
t Cyanodothiepin • Demexiptiline • Desipramine • Dibenzepine • Dimetacrine •
i Dosulepin/Dothiepin • Doxepin • Esmirtazapine • Fluotracen • Hepzidine •
d Homopipramol • Imipramine • Imipraminoxide • Intriptyline • Iprindole • Ketipramine •
 e
p
r Litracen • Lofepramine • Lortalamine • Losindole • Loxapine • Maprotiline • Mariptiline •
e Mazindol • Melitracen • Metapramine • Mezepine • Mianserin • Mirtazapine • Naranol •
s Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Oxaprotiline •
s Pipofezine • Pirandamine • Propizepine • Protriptyline • Quinupramine •
a Setiptiline/Teciptiline • Tandamine • Tampramine • Tianeptine • Tienopramine •
n Trimipramine
t
s

A
n
t
i
h
Alimemazine • Azatadine • Clobenzepam • Cyproheptadine • Dacemazine • Deptropine •
i
Desloratadine • Epinastine • Etymemazine • Hydroxyethylpromethazine •
s
Isopromethazine • Isothipendyl • Ketotifen • Latrepirdine • Loratadine • Mebhydrolin •
t
Mequitazine • Methdilazine • Olopatadine • Oxomemazine • Phenindamine • Pimethixene •
a
Promethazine • Propiomazine • Rupatadine • Thiazinamium
m
i
n
e
s

A
n
t
Acetophenazine • Amoxapine • Asenapine • Butaclamol • Butaperazine • Carphenazine •
i
Carpipramine • Chlorpromazine • Chlorprothixene • Ciclindole • Clocapramine •
p
Clomacran • Clotiapine • Clozapine • Flucindole • Fluotracen • Flupentixol •
s
Fluphenazine • Gevotroline • Homopipramol • Levomepromazine/Methotrimeprazine •
y
Loxapine • Maroxepin • Mesoridazine • Metitepine/Methiothepin • Mosapramine •
c
Naranol • Olanzapine • Perazine • Perphenazine • Periciazine • Piperacetazine •
h
Pipotiazine • Piquindone • Prochlorperazine • Promazine • Prothipendyl • Quetiapine •
o
Sulforidazine • Thiethylperazine • Thiopropazate • Thioridazine • Thiothixene •
t
Trifluoperazine • Triflupromazine • Zotepine • Zuclopenthixol
i
c
s

O
t
Atiprosin • Carbamazepine • Carvedilol • Cyclobenzaprine • Licarbazepine • Methylene
h
Blue • Monatepil • Oxcarbazepine • Pirenzepine • Pirolate • Pitrazepin • Pizotifen •
e
Profenamine
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