Ampicillin

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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 namesPrincipen
AHFS/Drugs.commonograph
MedlinePlusa685002
Pregnancy cat.A (Au), B (U.S.)
Legal status ?
RoutesOral, intravenous
Pharmacokinetic data
Bioavailability40% (oral)
Protein binding15 to 25%
Metabolism12 to 50%
Half-lifeapprox 1 hour
Excretion75 to 85% renal
Identifiers
CAS number69-53-4 YesY
ATC codeJ01CA01 S01AA19 QJ51CA01
PubChemCID 6249
DrugBankDB00415
ChemSpider6013 YesY
UNII7C782967RD YesY
KEGGD00204 YesY
ChEBICHEBI:28971 YesY
ChEMBLCHEMBL174 YesY
Chemical data
FormulaC16H19N3O4S 
Mol. mass349.41 g·mol−1
 YesY (what is this?)  (verify)
 
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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 namesPrincipen
AHFS/Drugs.commonograph
MedlinePlusa685002
Pregnancy cat.A (Au), B (U.S.)
Legal status ?
RoutesOral, intravenous
Pharmacokinetic data
Bioavailability40% (oral)
Protein binding15 to 25%
Metabolism12 to 50%
Half-lifeapprox 1 hour
Excretion75 to 85% renal
Identifiers
CAS number69-53-4 YesY
ATC codeJ01CA01 S01AA19 QJ51CA01
PubChemCID 6249
DrugBankDB00415
ChemSpider6013 YesY
UNII7C782967RD YesY
KEGGD00204 YesY
ChEBICHEBI:28971 YesY
ChEMBLCHEMBL174 YesY
Chemical data
FormulaC16H19N3O4S 
Mol. mass349.41 g·mol−1
 YesY (what is this?)  (verify)

Ampicillin is a beta-lactam antibiotic that 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.

Mechanism of action[edit]

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 G, or benzylpenicillin, 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 an irreversible 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[edit]

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 Solanum lycopersicum (tomato).[2]

Spectrum of Bacterial Susceptibility and Resistance[edit]

The bacteria Diplococcus pneumoniae and Haemophilus influenzae are susceptible to Ampicillin meanwhile Stenotrophomonas maltophilia developed resistance towards Ampicillin. Some of Neisseria gonorrhoeae are resistant to Ampicillin. For detailed information of Ampicillin, see Ampicillin Susceptibility and Resistance data sheet.[3]

Application[edit]

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 have become resistant to Ampicillin necessitating combination therapy or use of other antibiotics.

All Pseudomonas and most strains of Klebsiella and Aerobacter are considered resistant.[4] Additionally, resistance to ampicillin is seen in enterobacter, citrobacter, serratia, indole-positive proteus species, and other hospital-acquired gram negative infections.[5]

An ampicillin resistance gene (abbreviated ampR) 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.

History[edit]

Ampicillin 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.

References[edit]

  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 (Solanum lycopersicum). Journal of Plant Physiology 150, 137-140. [1]
  3. ^ "Ampicillin Susceptibility and Resistance Data". Retrieved 14 July 2013. 
  4. ^ Mosby's Drug Consult 2006 (16 ed.). Mosby, Inc. 2006. 
  5. ^ Katzung, Bertram G. (2007). Basic and Clinical Pharmacology, 10th edition. New York, NY: McGraw Hill Medical. p. 733. ISBN 978-0-07-145153-6. 

External links[edit]