oxacillin

Also known as 5-methyl-3-phenyl-4-isoxazolyl-penicillin, (2S,5R,6R)-3,3-dimethyl-6-{[(5-methyl-3-phenylisoxazol-4-yl)carbonyl]amino}-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, (5-methyl-3-phenyl-4-isoxazolyl)penicillin, 6beta-(5-methyl-3-phenylisoxazol-4-yl)penicillanic acid

Oxacillin (trade name Bactocill) is a narrow-spectrum second-generation beta-lactam antibiotic of the penicillin class developed by Beecham.

In the Vinony graph

Within Vinony's link graph, oxacillin is referenced by 219 other articles, and connects out to cephalosporin antibiotic, β-lactam antibiotic and ceftolozane/tazobactam.

Vinony files it under Drugboxes which contain changes to verified fields, Drugboxes which contain changes to watched fields and Drugs with no legal status.

Its subject is documented across 27 Wikipedia language editions.

Chemical data

Formula: C19H19N3O5S
Molecular weight: 401.4 g/mol
IUPAC name: (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
InChIKey: UWYHMGVUTGAWSP-JKIFEVAISA-N
XLogP: 2.4
Polar surface area: 138 Å²
H-bond donors: 2
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1971
Admin. routes: oral, parenteral
Indications: infection, bacteriemia, osteomyelitis, bacterial disease

via ChEMBL · EBI

Research

9,546 papers

Oxacillin-associated hepatitis.The American journal of gastroenterology · 1976
[The spread of oxacillin-resistant Staphylococcus aureus].Recenti progressi in medicina · 1995
Oxacillin-induced granulocytopenia.Acta haematologica · 1979
Regulation of bla system in ST59-related oxacillin-susceptible mecA-positive Staphylococcus aureus.The Journal of antimicrobial chemotherapy · 2022
Reversible oxacillin hepatotoxicity.The Journal of pediatrics · 1976

via PubMed

Wikidata facts

Subclass of: penicillin
Mass: 401.105
Has use: medication

Show 8 more facts

chemical formula: C₁₉H₁₉N₃O₅S
medical condition treated: staphylococcal infection
World Health Organisation international non-proprietary name: oxacillin
canonical SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O
isomeric SMILES: CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O
subject has role: bactericide
Commons category: Oxacillin
found in taxon: Pseudoalteromonas