Oxacillin

Oxacillin

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
Clinical data
Trade names	Bactocill
AHFS/Drugs.com	monograph
MedlinePlus	a685020
Legal status	?
Identifiers
CAS number	66-79-5 Y
ATC code	J01CF04 QJ51CF04
PubChem	CID 6196
DrugBank	DB00713
ChemSpider	5961 N
UNII	UH95VD7V76 Y
KEGG	D08307 Y
ChEBI	CHEBI:49566 N
ChEMBL	CHEMBL819 N
Chemical data
Formula	C19H19N3O5S
Mol. mass	401.436 g/mol
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
Physical data
Density	1.49 g/cm³
Boiling point	686.8 °C (1268 °F)
N (what is this?)  (verify)

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

It was developed by Beecham.^[1]

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, with the introduction and widespread use of both oxacillin and methicillin, antibiotic-resistant strains called oxacillin-resistant Staphylococcus aureus (MRSA/ORSA) have become increasingly prevalent worldwide. MRSA/ORSA is treated using vancomycin.

Adverse effects

Side effects include hypersensitivity and local reactions. In high doses, renal, hepatic, or nervous system effects can occur.^[2]

References