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.
In the Vinony graph
Vinony's link graph records 422 inbound references to benzylpenicillin, and connects out to ginkgolide, picrotoxin and antibiotic.
Vinony files it under Benzyl compounds, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.
Vinony links it to 41 Wikipedia language editions.
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
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1947
- Admin. routes
- oral, parenteral
- Indications
- osteomyelitis, rheumatic heart disease, syphilis, bacterial disease
via ChEMBL · EBI
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.