Ampicillin 1

Ampicillin
Ampicillin

Systematic (IUPAC) name

(2S,5R,6R)-6-([(2R)-2-amino-2-phenylacetyl]amino)
-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-
carboxylic acid
Identifiers

CAS number [1]

69-53-4

ATC code [2] [3] [4]

J01 CA01 S01 AA19 QJ51 CA01

PubChem [5]
CID 6249

DrugBank [6]
DB00415

ChemSpider [7]
6013

Chemical data

Formula C16H19N3O4S

Mol. mass 349.41 g·mol−1

SMILES [8] [9]

eMolecules & PubChem

Pharmacokinetic data

Bioavailability 40% (oral)

Protein binding 15 to 25%

Metabolism 12 to 50%

Half-life approx 1 hour

Excretion 75 to 85% renal

Therapeutic considerations

Pregnancy cat. A (Au), B (U.S.)

Legal status

Routes Oral, intravenous

[10]
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Ampicillin 2

Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. Until the
introduction of ampicillin by the British company Beecham, penicillin therapies had only been effective against
Gram-positive organisms such as staphylococci and streptococci. Ampicillin (originally branded as 'Penbritin') also
demonstrated activity against Gram-negative organisms such as H. influenzae, coliforms and Proteus spp. Ampicillin
was the first of a number of so-called broad spectrum penicillins subsequently introduced by Beecham. Ampicillin is
part of the aminopenicillin family and is roughly equivalent to its successor, amoxicillin in terms of spectrum and
level of activity[11] . It can sometimes result in reactions that range in severity from a rash (in the case of patients that
may unwittingly have mononucleosis) to potentially lethal allergic reactions such as anaphylaxis. However, as with
other penicillin drugs, it is relatively non-toxic and adverse effects of a serious nature are encountered only
infrequently.

Mechanism of action
Belonging to the penicillin group of beta-lactam antibiotics, ampicillin is able to penetrate Gram-positive and some
Gram-negative bacteria. It differs from penicillin only by the presence of an amino group. That amino group helps
the drug penetrate the outer membrane of gram-negative bacteria.
Ampicillin acts as a competitive inhibitor of the enzyme transpeptidase, which is needed by bacteria to make their
cell walls.[11] It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately
leads to cell lysis. The holes that appear in the cell walls allow the body’s immune system to take over and fight off
the bacteria. Ampicillin has received FDA approval for its action of mechanism.

Effects on chloroplast division

Ampicillin, like other β-lactam antibiotics, not only blocks the division of bacteria, but also the division of
chloroplasts of the Glaucophytes (called cyanelles) and chloroplasts of the moss Physcomitrella patens, a bryophyte.
In contrast, it has no effect on the plastids of the higher developed vascular plant Lycopersicon esculentum L.
(tomato) [12] .

Application
Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract
infections, otitis media, uncomplicated community-acquired pneumonia, Haemophilus influenzae, salmonellosis and
Listeria meningitis. It is used with flucloxacillin in the combination antibiotic co-fluampicil for empiric treatment of
cellulitis; providing cover against Group A streptococcal infection whilst the flucloxacillin acts against the
Staphylococcus aureus bacterium. Of concern is the number of bacteria that become resistant to Ampicillin
necessitating combination therapy or use of other antibiotics.
All Pseudomonas and most strains of Klebsiella and Aerobacter are considered resistant.[13]

Use in research
Ampicillin is often used as a selective agent in molecular biology to select for and to confirm the uptake of genes
(e.g., of plasmids) by bacteria (e.g., E. coli). A gene that is to be inserted into a bacterium is coupled to a gene coding
for an ampicillin resistance (in E. coli, usually the bla (TEM-1) gene, coding for β-lactamase). The treated bacteria
are then grown in a medium containing ampicillin (typically 50–100 mg/L). Only the bacteria that successfully take
up the desired genes become ampicillin resistant, and therefore contain the other desired gene as well. It can be used
with Cloaxicillin as well. As a powder ampicillin is white with slight yellow cast and is soluble in water
(150 mg/ml).
Ampicillin 3

References
[1] http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2009/ MB_cgi?term=69-53-4& rn=1
[2] http:/ / www. whocc. no/ atc_ddd_index/ ?code=J01CA01
[3] http:/ / www. whocc. no/ atc_ddd_index/ ?code=S01AA19
[4] http:/ / www. whocc. no/ atcvet/ atcvet_index/ ?code=QJ51CA01
[5] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=6249
[6] http:/ / www. drugbank. ca/ cgi-bin/ show_drug. cgi?CARD=DB00415
[7] http:/ / www. chemspider. com/ Chemical-Structure. 6013
[8] http:/ / www. emolecules. com/ cgi-bin/ search?t=ex&
q=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccccc1%29N%29%
[9] http:/ / pubchem. ncbi. nlm. nih. gov/ search/
?smarts=O%3DC%28O%29%5BC%40%40H%5D2N3C%28%3DO%29%5BC%40%40H%5D%28NC%28%3DO%29%5BC%40%40H%5D%28c1ccccc1%29N
[10] http:/ / en. wikipedia. org/ w/ index. php?& diff=cur& oldid=321808428
[11] AHFS DRUG INFORMATION 2006 (2006 ed.). American Society of Health-System Pharmacists. 2006.
[12] Britta Kasten und Ralf Reski (1997): β-lactam antibiotics inhibit chloroplast division in a moss (Physcomitrella patens) but not in tomato
(Lycopersicon esculentum). Journal of Plant Physiology 150, 137-140. (http:/ / cat. inist. fr/ ?aModele=afficheN& cpsidt=2640663)
[13] Mosby's Drug Consult 2006 (16 ed.). Mosby, Inc.. 2006.
Article Sources and Contributors 4

Article Sources and Contributors

Ampicillin  Source: http://en.wikipedia.org/w/index.php?oldid=379888677  Contributors: Alasdair, Alnokta, Anypodetos, Arcadian, AxelBoldt, Badgernet, Beetstra, Benjah-bmm27, Bernfarr,
Casforty, Chowbok, ClockworkSoul, ClockworkTroll, Conversion script, Courcelles, Davidruben, Ddorn 1999, Eakka, ElAmericano, Epbr123, Fvasconcellos, Fythrion, Giorgiogp2, Gogo Dodo,
Grafen, Gutsul, Harbinary, Heegoop, Hehkuviini, Heron, Jfdwolff, Jü, Kappa, Katalaveno, Kpjas, Linefeed, LittleT889, Lucas Duke, Lucubrator Lem, M1ss1ontomars2k4, M3a1xx, Magnus
Manske, MarcoTolo, Mcorazao, Michael Hardy, Mysid, Nikkimaria, Nirmos, Noisy, Nunh-huh, Outriggr, Pcworld08g, Phuzion, Pmaclean, RJHall, Rifleman 82, Rocaveli, Sabedon, Sabisteb,
Sedmic, Selket, Shaggyjacobs, Sirmelle, Slucas, Snow64, Techelf, Thricecube, Vedran12, Welsh, Wickey-nl, ‫طبلا يلع نسح‬, 85 anonymous edits

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