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.

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

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

Mass: 401.105

Show 5 more facts

chemical formula: C₁₉H₁₉N₃O₅S
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
Commons category: Oxacillin

Sources (4)

via Wikidata · CC0

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