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Ampicillin



Ampicillin
Systematic (IUPAC) name
7-(2-amino-2-phenyl-acetyl)amino-3,3
-dimethyl-6-oxo-2-thia-5-azabicyclo
[3.2.0]heptane-4-carboxylic acid
Identifiers
CAS number 69-53-4
ATC code J01CA01
PubChem 6249
DrugBank APRD00320
Chemical data
Formula C16H19N3O4S 
Mol. mass 349.406 g/mol
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

Ampicillin is a beta-lactam antibiotic that has been used extensively to treat bacterial infections since 1961. It is considered part of the aminopenicillin family and is roughly equivalent to amoxicillin in terms of spectrum and level of activity.[1] It can sometimes result in allergic reactions that range in severity from a rash (e.g. patients with mononucleosis) to potentially lethal anaphylaxis.

Additional recommended knowledge

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. The amino group helps the drug penetrate the outer membrane of gram-negative bacteria. Ampicillin acts as a competitive inhibitor of the enzyme transpeptidase. Transpeptidase is needed by bacteria to make their cell walls.[1] It inhibits the third and final stage of bacterial cell wall synthesis, which ultimately leads to cell lysis.

Indications

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.[2]

Use in research

Ampicillin is often used as a selective agent in molecular biology 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 on a medium containing ampicillin. Only the bacteria that successfully take up the desired genes become ampicillin resistant, and therefore contain the other desired gene as well.

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Ampicillin". A list of authors is available in Wikipedia.
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