Benzylpenicillin

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[[]]
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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:

• Cellulitis
• Bacterial endocarditis
• Gonorrhea
• Meningitis
• Aspiration pneumonia, lung abscess
• Community-acquired pneumonia
• Syphilis
• Septicemia in children
• Septic Arthritis

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.

Compendial status

• British Pharmacopoeia

References

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