| 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 | |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| MedlinePlus | a685013 |
| Pregnancy cat. | B(US) |
| Legal status | ℞ Prescription only |
| Routes | parenteral |
| Pharmacokinetic data | |
| Protein binding | 60 % |
| Metabolism | hepatic |
| Half-life | 30 min |
| Excretion | renal |
| Identifiers | |
| CAS number | 61-33-6 (free acid) 69-57-8 (sodium salt) |
| ATC code | J01CE01 S01AA14 QJ51CE01 |
| PubChem | CID 5904 |
| DrugBank | DB01053 |
| ChemSpider | 5693 |
| UNII | Q42T66VG0C |
| KEGG | D02336 |
| ChEBI | CHEBI:18208 |
| ChEMBL | CHEMBL29 |
| Chemical data | |
| Formula | C16H18N2O4S |
| Mol. mass | 334.4 g/mol |
| SMILES | eMolecules & PubChem |
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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.
Contents |
Specific indications for benzylpenicillin include:[1]
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).
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]