Benzylpenicillin

Benzylpenicillin
Clinical data


Trade names	Pfizerpen, other
AHFS/Drugs.com	International Drug Names
MedlinePlus	a685013
Pregnancy category	AU: A US: B (No risk in non-human studies)
Routes of administration	IV, IM
ATC code	J01CE01 (WHO) S01AA14 (WHO) QJ51CE01 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	60 %
Metabolism	Liver
Biological half-life	30 min
Excretion	Kidney
Identifiers
IUPAC name (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms	penicillin G potassium, penicillin G sodium
CAS Number	61-33-6^Y
PubChem CID	5904
IUPHAR/BPS	4796
DrugBank	DB01053^Y
ChemSpider	5693^Y
UNII	Q42T66VG0C
KEGG	D02336^N
ChEBI	CHEBI:18208^N
ChEMBL	CHEMBL29^N
E number	E705 (antibiotics)
ECHA InfoCard	100.000.461
Chemical and physical data
Formula	C₁₆H₁₈N₂O₄S
Molar mass	334.4 g/mol
3D model (Jmol)	Interactive image
SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C
InChI InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1^Y Key:JGSARLDLIJGVTE-MBNYWOFBSA-N^Y
^NY (what is this?)

Benzylpenicillin, also known as penicillin G, is an antibiotic used to treat a number of bacterial infections. This includes pneumonia, , syphilis, necrotizing enterocolitis, diphtheria, gas gangrene, leptospirosis, cellulitis, and tetanus. It is not a first-line agent for pneumococcal meningitis. Benzylpenicillin is given by injection into a vein or muscle. Two long acting forms benzathine benzylpenicillin and procaine benzylpenicillin are available for use by injection into a muscle.

Side effects include diarrhea, seizures, and allergic reactions including anaphylaxis. When used to treat syphilis a reaction known as Jarisch–Herxheimer may occur. It is not recommended in those with a history of penicillin allergy. Use during pregnancy is generally safe. It is in the penicillin and β-lactam class of medications.

Benzylpenicillin was discovered in 1929 and came into commercial use in 1942. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 0.24 to 2.72 USD per day. In the United States a course of treatment costs 100 to 200 USD.

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