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Oxacillin

Clinical data
ATC code	J01CF04 (WHO) QJ51CF04 (WHO)
Identifiers
IUPAC name (2S,5R,6R)-3,3-dimethyl-6--7-oxo-4-thia-1- azabicycloheptane-2-carboxylic acid
CAS Number	66-79-5
PubChem CID	6098
ChemSpider	5873
UNII	UH95VD7V76
KEGG	D08307
ChEMBL	ChEMBL891
CompTox Dashboard (EPA)	DTXSID8023397
ECHA InfoCard	100.000.577
Chemical and physical data
Formula	C19H19N3O5S
Molar mass	401.436 g/mol g·mol
3D model (JSmol)	Interactive image
Density	1.49 g/cm
Boiling point	686.8 °C (1,268.2 °F)
SMILES O=C(O)3N4C(=O)(NC(=O)c2c(onc2c1ccccc1Cl)C)4SC3(C)C
InChI InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1 Key:LQOLIRLGBULYKD-JKIFEVAISA-N
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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.

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.

References

1. David Greenwood (2008). Antimicrobial drugs: chronicle of a twentieth century medical triumph. Oxford University Press US. pp. 124–. ISBN 9780199534845. Retrieved 18 November 2010.

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