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
Clinical data
Trade names Principen
AHFS/Drugs.com monograph
MedlinePlus a685002
Pregnancy cat. A (Au), B (U.S.)
Legal status  ?
Routes Oral, intravenous
Pharmacokinetic data
Bioavailability 40% (oral)
Protein binding 15 to 25%
Metabolism 12 to 50%
Half-life approx 1 hour
Excretion 75 to 85% renal
Identifiers
CAS number 69-53-4 YesY
ATC code J01CA01 S01AA19 QJ51CA01
PubChem CID 6249
DrugBank DB00415
ChemSpider 6013 YesY
UNII 7C782967RD YesY
KEGG D00204 YesY
ChEBI CHEBI:28971 YesY
ChEMBL CHEMBL174 YesY
Chemical data
Formula C16H19N3O4S 
Mol. mass 349.41 g·mol−1
SMILES eMolecules & PubChem
 YesY(what is this?)  (verify)

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.[1] 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 rarely.

Contents

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.[1] It inhibits the third and final stage of bacterial cell wall synthesis in binary fission, which ultimately leads to cell lysis. Ampicillin has received FDA approval for its mechanism of action.

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).[2]

Application

Ampicillin is closely related to amoxicillin, another type of penicillin, and both are used to treat urinary tract infections, otitis media, 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.[3]

An ampicillin resistance gene (abbreviated bla) is commonly used as a selectable marker in routine biotechnology. Due to concerns over horizontal gene transfer to pathogenic organisms in the wild, the European Food Safety Authority restricts use of this gene (among other resistance genes) in commercial genetically modified organisms. The enzyme responsible for degrading ampicillin is called beta-lactamase, in reference to the beta-lactam structure of ampicillin and related drugs.

References

  1. ^ a b AHFS DRUG INFORMATION 2006 (2006 ed.). American Society of Health-System Pharmacists. 2006. 
  2. ^ 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. [1]
  3. ^ Mosby's Drug Consult 2006 (16 ed.). Mosby, Inc.. 2006. 

External links


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Look at other dictionaries:

  • ampicillin — n. 1. a semisynthetic penicillin which can be considered as the common benzylpenicillin containing an amino group at the alpha benzyl position. Note: It is more active against certain gram negative bacteria than is benzylpenicillin. It found wide …   The Collaborative International Dictionary of English

  • Ampicillin — См. Ампициллин (Источник: «Словарь терминов микробиологии») …   Словарь микробиологии

  • ampicillin — [am΄pə sil′in] n. a synthetic antibiotic, C16H19N3O4S, derived from penicillin, having resistance to acids so that it can be taken orally to fight a wide range of bacterial infections …   English World dictionary

  • Ampicillin — Strukturformel Allgemeines Freiname Ampicillin …   Deutsch Wikipedia

  • ampicillin — /am peuh sil in/, n. Pharm. a broad spectrum semisynthetic penicillin, C16H19N3O4S, effective against certain susceptible Gram positive and Gram negative bacteria. [1965 70; prob. am(inobenzyl)p(en)icillin, an alternate chemical name] * * * ▪… …   Universalium

  • ampicillin — Penicillin derivative with broad spectrum activity; ampicillin resistance is often used as a marker for plasmid transfer in genetic engineering (eg. pBR322 is ampicillin resistant) …   Dictionary of molecular biology

  • Ampicillin — Am|pi|cil|lin [Kurzw. aus 6 (α Amino α phenylacetamido)penicillansäure], das; s: Freiname für ein halbsynthetisches Derivat des Penicillins. * * * Ampicillin   das, s, Penicilline …   Universal-Lexikon

  • ampicillin — noun Etymology: amino + penicillin Date: 1961 a penicillin C16H19N3O4S that is effective against gram negative and gram positive bacteria and is used to treat various infections of the urinary, respiratory, and …   New Collegiate Dictionary

  • ampicillin — noun /æm.pɪ sɪ lɪn/lang=en A broad spectrum antibiotic having a beta lactam structure …   Wiktionary

  • ampicillin — An acid stable semisynthetic penicillin derived from 6 aminopenicillanic acid; it has a broader spectrum of antimicrobial action than penicillin G, inhibits the growth of Gram positive and Gram negative bacteria, and is not resist …   Medical dictionary

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