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. 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).

Compendial status

• British Pharmacopoeia

References

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