Name Amoxicillin

Accession
DB01060 (APRD00248)
Number
Type Small Molecule
Groups Approved
A broad-spectrum semisynthetic antibiotic similar to ampicillin except that its
resistance to gastric acid permits higher serum levels with oral administration.
Description
Amoxicillin is commonly prescribed with clauvanic acid (a beta lactamase
inhibitor) as it is susceptible to beta-lacatamase degradation. [PubChem]

Structure

Brand mixtures

Brand Name Ingredients

Augmentin amoxicillin + clavulanic acid
Co-
amoxicillin + clavulanic acid
amoxiclav
Prevpac amoxicillin + clarithromycin + lansoprazole
 Anti-Bacterial Agents
Categories  Penicillins

CAS number 26787-78-0

Average: 365.404
Weight
Monoisotopic: 365.104541423
Chemical Formula C16H19N3O5S
InChI Key LSQZJLSUYDQPKJ-NJBDSQKTSA-N
InChI=1S/C16H19N3O5S/c1-
16(2)11(15(23)24)19-13(22)10(14(19)25-
InChI 16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-
11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-
,10-,11+,14-/m1/s1
(2S,5R,6R)-6-[(2R)-2-amino-2-(4-
hydroxyphenyl)acetamido]-3,3-dimethyl-7-
IUPAC Name
oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-
carboxylic acid
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@
SMILES H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(
O)=O
Mass Spec Not Available
Taxonomy
 Kingdom Organic Compounds
Superclass Heterocyclic Compounds
Class Lactams
Subclass Beta Lactams
Direct parent Penicillins
N-acyl-alpha Amino Acids and Derivatives;
Alpha Amino Acid Amides; Phenols and
Derivatives; Tertiary Carboxylic Acid Amides;
Thiazolidines; Polyols; Hemiaminals;
Alternative parents
Secondary Carboxylic Acid Amides; Tertiary
Amines; Azetidines; Polyamines; Enols;
Enolates; Carboxylic Acids; Aminals;
Thioethers; Monoalkylamines
n-acyl-alpha amino acid or derivative; alpha-
amino acid amide; alpha-amino acid or
derivative; phenol derivative; benzene;
thiazolidine; tertiary carboxylic acid amide;
carboxamide group; tertiary amine; polyol;
Substituents
hemiaminal; azetidine; secondary carboxylic
acid amide; polyamine; aminal; carboxylic acid
derivative; enolate; thioether; enol; carboxylic
acid; primary amine; primary aliphatic amine;
amine; organonitrogen compound
This compound belongs to the penicillins.
These are organic compounds containing the
penicillin core structure, which is structurally
Classification description characterized by a penam ring bearing two
methyl groups at position 2, and an amide
group at position 6 [starting from the sulfur
atom at position 1].
Pharmacology
For the treatment of infections of the ear, nose,
and throat, the genitourinary tract, the skin and
skin structure, and the lower respiratory tract
due to susceptible (only b-lactamase-negative)
strains of Streptococcus spp. (a- and b-
Indication hemolytic strains only), S. pneumoniae,
Staphylococcus spp., H. influenzae, E. coli, P.
mirabilis, or E. faecalis. Also for the treatment
of acute, uncomplicated gonorrhea (ano-genital
and urethral infections) due to N. gonorrhoeae
(males and females).
Amoxicillin is a moderate-spectrum antibiotic
active against a wide range of Gram-positive,
and a limited range of Gram-negative
Pharmacodynamics
organisms. It is usually the drug of choice
within the class because it is better absorbed,
following oral administration, than other beta-
 lactam antibiotics. Amoxicillin is susceptible to
degradation by β-lactamase-producing bacteria,
and so may be given with clavulanic acid to
increase its susceptability. The incidence of β-
lactamase-producing resistant organisms,
including E. coli, appears to be increasing.
Amoxicillin is sometimes combined with
clavulanic acid, a β-lactamase inhibitor, to
increase the spectrum of action against Gram-
negative organisms, and to overcome bacterial
antibiotic resistance mediated through β-
lactamase production.
Amoxicillin binds to penicillin-binding protein
1A (PBP-1A) located inside the bacterial cell
well. Penicillins acylate the penicillin-sensitive
transpeptidase C-terminal domain by opening
the lactam ring. This inactivation of the
enzyme prevents the formation of a cross-link
Mechanism of action
of two linear peptidoglycan strands, inhibiting
the third and last stage of bacterial cell wall
synthesis. Cell lysis is then mediated by
bacterial cell wall autolytic enzymes such as
autolysins; it is possible that amoxicllin
interferes with an autolysin inhibitor.
Absorption Rapidly absorbed after oral administration.
Volume of distribution Not Available
In blood serum, amoxicillin is approximately
Protein binding
20% protein-bound
Hepatic metabolism accounts for less than 30%
Metabolism
of the biotransformation of most penicillins
Most of the amoxicillin is excreted unchanged
Route of elimination in the urine; its excretion can be delayed by
concurrent administration of probenecid.
Half life 61.3 minutes
Clearance Not Available
Serious toxicity is unlikely following large
doses of amoxicillin. Acute ingestion of large
doses of amoxicillin may cause nausea,
Toxicity
vomiting, diarrhea and abdominal pain. Acute
oliguric renal failure and hematuria may occur
following large doses.
 Enteric bacteria and other eubacteria
Affected organisms
Pathways Not Available
SNP Mediated Effects Not Available
SNP Mediated Adverse Drug Reactions Not Available
ADMET
 Property Value Probability
Human Intestinal
- 0.9008
Absorption
Blood Brain
- 0.9967
Barrier
Caco-2
- 0.8722
permeable
P-glycoprotein
Substrate 0.5741
substrate
P-glycoprotein
Non-inhibitor 0.9665
inhibitor I
P-glycoprotein
Non-inhibitor 0.9968
inhibitor II
Renal organic
cation Non-inhibitor 0.9636
transporter
CYP450 2C9
Non-substrate 0.843
substrate
CYP450 2D6
Non-substrate 0.8446
substrate
CYP450 3A4
Non-substrate 0.5478
substrate
Predicted ADMET features CYP450 1A2
Non-inhibitor 0.9045
substrate
CYP450 2C9
Non-inhibitor 0.907
substrate
CYP450 2D6
Non-inhibitor 0.9231
substrate
CYP450 2C19
Non-inhibitor 0.915
substrate
CYP450 3A4
Non-inhibitor 0.8309
substrate
CYP450 Low CYP
inhibitory Inhibitory 0.9767
promiscuity Promiscuity
Non AMES
Ames test 0.9099
toxic
Non-
Carcinogenicity 0.5439
carcinogens
Not ready
Biodegradation 0.9606
biodegradable
Rat acute 1.7036 LD50, Not
toxicity mol/kg applicable
hERG inhibition
Weak inhibitor 0.9996
(predictor I)
 hERG inhibition
Non-inhibitor 0.8761
(predictor II)
Pharmacoeconomics
 American antibiotics llc
 Aurobindo pharma ltd
 Dava pharmaceuticals inc
 Hikma pharmaceuticals
 Laboratorios atral sarl
 Mylan pharmaceuticals inc
 Ranbaxy pharmaceuticals inc
 Sandoz inc
 Teva pharmaceuticals usa inc
Manufacturers  Glaxosmithkline
 Apothecon inc div bristol myers squibb
 Apothecon sub bristol myers squibb co
 Parke davis div warner lambert co
 Wyeth ayerst laboratories
 Wockhardt eu operations (swiss) ag
 Ranbaxy laboratories ltd
 Middlebrook pharmaceuticals inc
 Draximage inc

 Altura Pharmaceuticals Inc.

 American Antibiotics LLC
 Apotheca Inc.
 A-S Medication Solutions LLC
 Aurobindo Pharma Ltd.
 Blenheim Pharmacal
 Bristol-Myers Squibb Co.
 Bryant Ranch Prepack
 C.O. Truxton Inc.
 Cardinal Health
 Carlisle Laboratories Inc.
 Casa De Amigos Pharmacy
 Clonmel Healthcare Ltd.
Packagers  Comprehensive Consultant Services
Inc.
 Darby Dental Supply Co. Inc.
 DAVA Pharmaceuticals
 Dept Health Central Pharmacy
 Direct Dispensing Inc.
 Dispensing Solutions
 Diversified Healthcare Services Inc.
 DNA Pharmaceuticals
 E.R. Squibb and Sons LLC
 GlaxoSmithKline Inc.
 Golden State Medical Supply Inc.
 Greenstone LLC
 H.J. Harkins Co. Inc.
  Hikma Pharmaceuticals
 Innoviant Pharmacy Inc.
 International Ethical Labs Inc.
 Keltman Pharmaceuticals Inc.
 Laboratorios Atral Sarl
 Lake Erie Medical and Surgical Supply
 Liberty Pharmaceuticals
 Major Pharmaceuticals
 Medpharm Inc.
 Medvantx Inc.
 Middlebrook Pharmaceuticals
 Mississippi State Dept Health
 Murfreesboro Pharmaceutical Nursing
Supply
 Novopharm Ltd.
 Nucare Pharmaceuticals Inc.
 Okasa Pvt Ltd.
 Palmetto Pharmaceuticals Inc.
 Par Pharmaceuticals
 Patient First Corp.
 PCA LLC
 PD-Rx Pharmaceuticals Inc.
 Pharmedix
 Physicians Total Care Inc.
 Poli Industria Chimica SPA
 Preferred Pharmaceuticals Inc.
 Prepackage Specialists
 Prepak Systems Inc.
 Prescription Dispensing Service Inc.
 Putney Inc.
 Qualitest
 Ranbaxy Laboratories
 Rebel Distributors Corp.
 Redpharm Drug
 Reid Provident Laboratories Inc.
 Sandhills Packaging Inc.
 Sandoz
 Signal Health Ltd.
 Southwood Pharmaceuticals
 St Mary's Medical Park Pharmacy
 Stat Rx Usa
 Stat Scripts LLC
 Talbert Medical Management Corp.
 Teva Pharmaceutical Industries Ltd.
 Tya Pharmaceuticals
 UDL Laboratories
 Veratex Corp.
 West-Ward Pharmaceuticals

Dosage forms Show

entries
Form Route Strength
Capsule Oral
Powder, for solution Oral
Powder, for suspension Oral
Suspension Oral
Tablet Oral

Patents Show

Patent Expires
Countr Approve
Numbe (estimate
y d
r d)
United 654455 2000-10- 2020-10-
States 5 13 13
Properties
State solid
Property Value Source
melting point 194 °C Not Available
3430
water solubility Not Available
Experimental Properties mg/L
logP 0.87 SANGSTER (1994)
Caco2 ADME Research,
-6.1
permeability USCD
Property Value Source
Water Solubility 0.958 ALOGPS
logP 0.75 ALOGPS
logP -2.3 ChemAxon
logS -2.6 ALOGPS
pKa (Strongest Acidic) 3.23 ChemAxon
pKa (Strongest Basic) 7.43 ChemAxon
Predicted Properties Physiological Charge 0 ChemAxon
Hydrogen Acceptor
6 ChemAxon
Count
Hydrogen Donor Count 4 ChemAxon
2
Polar Surface Area 132.96 Å ChemAxon
Rotatable Bond Count 4 ChemAxon
3 -
89.5 m ·mol
Refractivity 1 ChemAxon
Polarizability 35.53 Å3 ChemAxon
 Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five Yes ChemAxon
Ghose Filter No ChemAxon
Veber's Rule No ChemAxon
MDDR-like Rule No ChemAxon
Spectra
Spectra Not Available
References
Joan Cabre, Jose Diago, Asuncion Esteve, Johannes
Ludescher, “Production of a crystalline salt of
amoxicillin.” U.S. Patent US6103897, issued April,
Synthesis Reference
1971.

US6103897
1. Drawz SM, Bonomo RA: Three decades of
beta-lactamase inhibitors. Clin Microbiol
General Reference
Rev. 2010 Jan;23(1):160-201. Pubmed

Resource Link
KEGG
C06827
Compound
PubChem
33613
Compound
PubChem
46507578
Substance
ChemSpid
31006
er
ChEBI 2676
ChEMBL CHEMBL1082
External Links Therapeuti
c Targets DAP000443
Database
PharmGK
PA448406
B
Drug
Product 2262886
Database
http://www.rxlist.com/cgi/generic/amox
RxList
.htm
Drugs.com http://www.drugs.com/amoxicillin.html
Wikipedia Amoxicillin
ATC Codes J01CA04
  J — ANTIINFECTIVES FOR SYSTEMIC
USE
 J01 — ANTIBACTERIALS FOR
SYSTEMIC USE
 J01C — BETA-LACTAM
ANTIBACTERIALS, PENICILLINS
 J01CA — Penicillins with extended spectrum

 08:12.16.08
AHFS Codes
PDB Entries Not Available
FDA label show(49.6 KB)
MSDS show(38.1 KB)
Interactions
Drug
Demeclocycline Possible antagonism of action
Doxycycline Possible antagonism of action
This anti-infectious agent could
Ethinyl
decrease the effect of the oral
Estradiol
contraceptive
This anti-infectious agent could
Mestranol decrease the effect of the oral
Drug Interactions contraceptive
Methacycline Possible antagonism of action
The penicillin increases the effect
Methotrexate
and toxicity of methotrexate
Minocycline Possible antagonism of action
Oxytetracycline Possible antagonism of action
Rolitetracycline Possible antagonism of action
Tetracycline Possible antagonism of action
 Take without regard to meals.
Food Interactions

Targets

1. Penicillin-binding protein 1A

Kind: protein

Organism: Clostridium perfringens (strain 13 / Type A)

Pharmacological action: yes

Actions: inhibitor
Components

Name UniProt ID Details

Penicillin-binding protein 1A Q8XJ01

References:

1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat
Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of
drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
3. Okamoto T, Yoshiyama H, Nakazawa T, Park ID, Chang MW, Yanai H, Okita K,
Shirai M: A change in PBP1 is involved in amoxicillin resistance of clinical isolates
of Helicobacter pylori. J Antimicrob Chemother. 2002 Dec;50(6):849-56. Pubmed

Enzymes

1. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details

Cytochrome P450 2C19 P33261

References:

1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S,

Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on
Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions.
Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24.
Pubmed

Transporters
 Name UniProt ID Details
1. Solute carrier family 15 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details

Solute carrier family 15 member 1 P46059

References:

1. Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport

characteristics of differently charged cephalosporin antibiotics in oocytes expressing
the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J
Pharmacol Exp Ther. 1996 May;277(2):831-9. Pubmed
2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide
symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J
Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed
3. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat
peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997
Nov;273(5 Pt 2):F706-11. Pubmed
4. Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions
between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter
hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. Pubmed
5. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of
amoxicillin and cefaclor with human renal organic anion and peptide transporters.
Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed

2. Solute carrier family 15 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor
 Name UniProt ID Details
Components

Name UniProt ID Details

Solute carrier family 15 member 2 Q16348

References:

1. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat

peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997
Nov;273(5 Pt 2):F706-11. Pubmed
2. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide
symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J
Pharm Biopharm. 2005 Jan;59(1):17-24. Pubmed
3. Li M, Anderson GD, Phillips BR, Kong W, Shen DD, Wang J: Interactions of
amoxicillin and cefaclor with human renal organic anion and peptide transporters.
Drug Metab Dispos. 2006 Apr;34(4):547-55. Epub 2006 Jan 24. Pubmed

3. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details

Solute carrier family 22 member 6 Q4U2R8

References:

1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H:

The interaction and transport of beta-lactam antibiotics with the cloned rat renal
organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. Pubmed