Oxacillin

Oxacillin

Clinical data
Trade names	Bactocill
AHFS/Drugs.com
MedlinePlus	a685020
ATC code	J01CF04 (WHO) QJ51CF04 (WHO)
Identifiers
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
CAS Number	66-79-5 Y
PubChem CID	6196
DrugBank	DB00713 N
ChemSpider	5961 N
UNII	UH95VD7V76
KEGG	D08307 Y
ChEBI	CHEBI:7809 N
ChEMBL	CHEMBL819 N
ECHA InfoCard	100.000.577
Chemical and physical data
Formula	C19H19N3O5S
Molar mass	401.436 g/mol
3D model (Jmol)	Interactive image
Density	1.49 g/cm3
Boiling point	686.8 °C (1,268.2 °F)
SMILES Cc1c(c(no1)c2ccccc2)/C(N/[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O)=O
InChI InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1 N Key:UWYHMGVUTGAWSP-JKIFEVAISA-N N
NY (what is this?)

Oxacillin sodium (trade name Bactocill) is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.

Oxacillin is a penicillinase-resistant β-lactam. It is similar to methicillin, and has replaced methicillin in clinical use. Other related compounds are nafcillin, cloxacillin, dicloxacillin, and flucloxacillin. 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, with the introduction and widespread use of both oxacillin and methicillin, antibiotic-resistant strains called methicillin-resistant and oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) have become increasingly prevalent worldwide. MRSA/ORSA is treated using vancomycin.

Side effects include hypersensitivity and local reactions. In high doses, renal, hepatic, or nervous system effects can occur.