Structure via PubChem · Public domain (PubChem)
oxacillin
Sign in to saveAlso 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 Ų
- 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
~5 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- Pharmacology
- Mechanism of action
- Chemistry
- History
- Society and culture
- U.S. Food and Drug Administration approval history
- Pricing
- References
Oxacillin (trade name Bactocill) is a narrow-spectrum second-generation beta-lactam antibiotic of the penicillin class developed by Beecham.
It was patented in 1960 and approved for medical use in 1962.
Excerpted from Wikipedia’s “oxacillin” article, available under the CC BY-SA 4.0 licence.