Difference between revisions of "Benzylpenicillin"

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Benzylpenicillin
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Systematic (IUPAC) name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenylacetyl)amino)- (2S-(2α,5α,6β))-
Clinical data
Pregnancy
category
  • US: B (No risk in non-human studies)
Routes of
administration		 parenteral
Legal status
Legal status
  • ℞ (Prescription only)
Pharmacokinetic data
Protein binding 60 %
Metabolism hepatic
Biological half-life 30 min
Excretion renal
Identifiers
CAS Number 61-33-6 (free acid)
69-57-8 (sodium salt)
ATC code J01CE01 (WHO) S01AA14 QJ51CE01
PubChem CID 5904
DrugBank DB01053
Chemical data
Formula C16H18N2O4S
Molar mass 334.4 g/mol[[Script error: No such module "String".]]
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Benzylpenicillin, commonly known as penicillin G, is the gold standard type of penicillin. 'G' in the name 'Penicillin G' refers to 'Gold Standard'. Penicillin G is typically given by a parenteral route of administration (not orally) because it is unstable in the hydrochloric acid of the stomach. Because the drug is given parenterally, higher tissue concentrations of penicillin G can be achieved than is possible with phenoxymethylpenicillin. These higher concentrations translate to increased antibacterial activity.

Specific indications for benzylpenicillin include:[1]

Side Effects

Adverse affect can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction. Rarely CNS toxicity including convulsions (especially with high doses or in severe renal impairment), interstitial nephritis, haemolytic anaemia, leucopenia, thrombocytopenia, and coagulation disorders. Also reported diarrhoea (including antibiotic-associated colitis).

Toxicology

Benzylpenicillin serum concentrations can be monitored either by traditional microbiological assay or by more modern chromatographic techniques. Such measurements can be useful to avoid central nervous system toxicity in any patient receiving large doses of the drug on a chronic basis, but they are especially relevant to patients with renal failure, who may accumulate the drug due to reduced urinary excretion rates.[2][3]

Compendial status

References

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Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) · DADAL/AR inhibitors (Cycloserine) · bactoprenol inhibitors (Bacitracin)
Glycopeptide
inhibit PG chain elongation: Vancomycin# (Oritavancin, Telavancin) · Teicoplanin (Dalbavancin) · Ramoplanin
β-lactams/
(inhibit PBP
cross-links)
Combinations
Other

M: BAC

drug(J1p, w, n, m, vacc)

da:Benzylpenicillin

de:Benzylpenicillin es:Bencilpenicilina hr:Benzilpenicilin it:Benzilpenicillina hu:Benzilpenicillin nl:Benzylpenicilline pl:Benzylopenicylina pt:Benzilpenicilina sl:Penicilin G fi:G-penisilliini

th:เบนซิลเพนิซิลลิน
  1. ↑ Rossi S, editor, ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook. ISBN 0-9757919-2-3. 
  2. ↑ Fossieck B Jr, Parker RH. Neurotoxicity during intravenous infusion of penicillin. A review. J. Clin. Pharmacol. 14: 504- 512, 1974.
  3. ↑ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1195-1196.
  4. ↑ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Retrieved 26 March 2010. 
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