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 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
9,546 papersArticle
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.