Oxacillin
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| Systematic (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 |
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| Clinical data | |
| Trade names | Bactocill |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a685020 |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 66-79-5  |
| ATC code | J01CF04 QJ51CF04 |
| PubChem | CID 6098 |
| DrugBank | DB00713 |
| ChemSpider | 5873 |
| UNII | UH95VD7V76 |
| KEGG | D08307 |
| ChEBI | CHEBI:49566  |
| ChEMBL | CHEMBL891 |
| Chemical data | |
| Formula | C19H19N3O5S |
| Mol. mass | 401.436 g/mol |
| SMILES | eMolecules & PubChem |
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| Physical data | |
| Density | 1.49 g/cm³ |
| Boiling point | 686.8 °C (1268 °F) |
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Oxacillin sodium (trade name Bactocill) is a narrow spectrum beta-lactam antibiotic of the penicillin class.
It was developed by Beecham.[1]
[edit] Uses
Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Another related compound is nafcillin. Since it is resistant to penicillinase enzymes, such as that produced by Staphylococcus aureus, it is widely used clinically in the US to treat penicillin-resistant Staphylococcus aureus. However, resistant strains called oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) are highly prevalent in the U.S. and the U.K.
[edit] Adverse effects
Oxacillin can cause hepatitis.
[edit] References
- ^ David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 9780199534845. http://books.google.com/books?id=i4_FZHmzjzwC&pg=PA124. Retrieved 18 November 2010.
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