File:Benzylpenicillin.svg · Wikimedia Commons · See Wikimedia Commons
benzylpenicillin
Sign in to saveAlso known as penicillin G sodium, penicillin-G potassium, (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-(2-phenylacetamido)penicillanic acid, free penicillin II, benzylpenicillinic acid, PG, bensylpenicillin
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 b
OverviewAI-generated
Benzylpenicillin is a chemical compound with the formula C₁₆H₁₈N₂O₄S. Its IUPAC name is (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid. The substance has a mass of 334.099 and a weight of 334.4.
Chemical properties include an xlogp of 1.8 and a topological polar surface area of 112. The molecule contains two hydrogen bond donors and five hydrogen bond acceptors, with a charge of 0. It is referenced by 422 other encyclopedia articles and has 123512 associated PubMed entries.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Chemical data
- Formula
- C16H18N2O4S
- Molecular weight
- 334.4 g/mol
- IUPAC name
- (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
- InChIKey
- JGSARLDLIJGVTE-MBNYWOFBSA-N
- XLogP
- 1.8
- Polar surface area
- 112 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
123,512 papers- Treatment outcomes with benzylpenicillin and non-benzylpenicillin antibiotics, and the performance of the penicillin zone-edge test versus molecular detection of blaZ in penicillin-susceptible Staphylococcus aureus (PSSA) bacteraemia.The Journal of antimicrobial chemotherapy · 2023
- Benzylpenicillin-induced prolonged cholestasis.The Annals of pharmacotherapy · 2001
- ENZYMATIC DEACYLATION OF S35-BENZYLPENICILLIN.Journal of bacteriology · 1965
- SYNTHETIC benzylpenicillin.American professional pharmacist · 1947
- SYNTHESIS of benzylpenicillin.Journal of the American Pharmaceutical Association. American Pharmaceutical Association · 1946
via PubMed
Wikidata facts
- Has part
- carbon
- Mass
- 334.099
- Has use
- medication
Show 8 more facts
- chemical formula
- C₁₆H₁₈N₂O₄S
- canonical SMILES
- CC1(C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
- isomeric SMILES
- CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CC=C3)C(=O)O)C
- World Health Organisation international non-proprietary name
- benzylpenicillin
- medical condition treated
- botulism
- Commons category
- Benzylpenicillin
- subject has role
- bactericide
- found in taxon
- Penicillium rubrum
Sources (6)
via Wikidata · CC0
~4 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Antimicrobial potency
- Adverse effects
- Manufacture
- Synonyms
- References
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.
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.
Excerpted from Wikipedia’s “benzylpenicillin” article, available under the CC BY-SA 4.0 licence.