Benzylpenicillin
Systematic (IUPAC) name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Clinical data
Trade names BenPen
AHFS/Drugs.com
MedlinePlus
Pregnancy
category
  • AU: A
  • US: B (No risk in non-human studies)
Legal status
  • (Prescription only)
Routes of
administration
Intravenous, Intramuscular, formerly used orally
Pharmacokinetic data
Protein binding 60 %
Metabolism hepatic
Biological half-life 30 min
Excretion renal
Identifiers
CAS Registry Number  YesY (free acid)
69-57-8 (sodium salt)
ATC code J01 S01 QJ51
PubChem CID:
IUPHAR/BPS
DrugBank  YesY
ChemSpider  YesY
UNII  YesY
KEGG  N
ChEBI  N
ChEMBL  N
Chemical data
Formula C16H18N2O4S
Molecular mass 334.4 g/mol
 N   
2,400,000 units of Bicillin L-A brand of benzylpenicillin, for deep intramuscular injection

Benzylpenicillin (health system.[2]

Medical uses

Specific indications for benzylpenicillin include:[3]

Antimicrobial potency

As an antibiotic, Penicillin G is noted to possess effectiveness mainly against Neisseria gonorrhoeae and Neisseria meningitidis are also reported to be susceptible to Penicillin G.[4]

Adverse effects

Adverse effects 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).


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 person 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.[5][6]

Compendial status

References

  1. ^
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  5. ^ Fossieck B Jr, Parker RH. Neurotoxicity during intravenous infusion of penicillin. A review. J. Clin. Pharmacol. 14: 504- 512, 1974.
  6. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1195-1196.
  7. ^