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Oxacillin sodium

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/10/28 22:09:36」(JST)

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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
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	66-79-5 Y
ATC code	J01CF04 QJ51CF04
PubChem	CID 6098
DrugBank	DB00713
ChemSpider	5873 Y
UNII	UH95VD7V76 Y
KEGG	D08307 Y
ChEBI	CHEBI:49566 N
ChEMBL	CHEMBL891 Y
Chemical data
Formula	C19H19N3O5S
Mol. mass	401.436 g/mol
SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1ccccc1Cl)C)[C@H]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 Y Key:LQOLIRLGBULYKD-JKIFEVAISA-N Y
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.

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

Further information: Penicillin drug reaction

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

References

English Journal

• High performance liquid chromatography for the simultaneous analysis of penicillin residues in beef and milk using ion-paired extraction and binary water-acetonitrile mixture.

• Kukusamude C, Burakham R, Chailapakul O, Srijaranai S.SourceDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen 40002, Thailand.
• Talanta.Talanta.2012 Apr 15;92:38-44. Epub 2012 Jan 25.
• An ion-paired extraction (IPE) has been developed for the analysis of penicillin antibiotics (penicillin G, oxacillin and cloxacillin) in beef and milk samples using tetrabutylammonium bromide (TBABr) as ion-pairing agent and binary water-acetonitrile as extractant. The factors affecting the IPE eff
• PMID 22385805

• Detection and analysis of Staphylococcus aureus isolates found in ambulances in the Chicago metropolitan area.

• Rago JV, Buhs LK, Makarovaite V, Patel E, Pomeroy M, Yasmine C.SourceDepartment of Biology, Lewis University, Romeoville, IL.
• American journal of infection control.Am J Infect Control.2012 Apr;40(3):201-5.
• BACKGROUND: Given the frequency with which many different strains of Staphylococcus aureus are found in various prehospital settings, this study sought to characterize S aureus isolates taken from one such environment. The objectives were to determine the frequency of S aureus in front-line, advance
• PMID 22440671

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