Benzylpenicillin

Benzylpenicillin, also known as penicillin G (PenG) or BENPEN, is an antibiotic used to treat a number of bacterial infections. This includes pneumonia, strep throat, syphilis, necrotizing enterocolitis, diphtheria, gas gangrene, leptospirosis, cellulitis, and tetanus. It is not a first-line agent for pneumococcal meningitis. Due to benzylpenicillin's limited bioavailability for oral medications, it is generally taken as an injection in the form of a sodium, potassium, benzathine, or procaine salt. 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 only.

Benzylpenicillin
Ball and stick model. Legend:
Blue=nitrogen; red=oxygen; yellow=sulfur
grey=carbon and carbon bonds; white=hydrogen.
Clinical data
Trade namesPfizerpen, other
Other namesPenicillin G potassium, penicillin G sodium
AHFS/Drugs.comInternational Drug Names
MedlinePlusa685013
Pregnancy
category
  • AU: A
Routes of
administration		Intravenous therapy, intramuscular injection
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30% oral
Protein binding60%
MetabolismLiver
Elimination half-life30 min
ExcretionKidney
Identifiers
  • (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E numberE705 (antibiotics)
CompTox Dashboard (EPA)
ECHA InfoCard100.000.461
Chemical and physical data
FormulaC16H18N2O4S
Molar mass334.39 g·mol−1
3D model (JSmol)
SMILES
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C
  • 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?)  (verify)

Side effects include diarrhea, seizures, and allergic reactions including anaphylaxis. When used to treat syphilis or Lyme disease 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 in the penicillin and β-lactam class of medications.

Benzylpenicillin is on the World Health Organization's List of Essential Medicines.

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