Oxacillin

Structural formula
General
Non-proprietary name	Oxacillin
other names	(2 S , 5 R , 6 R ) -3,3-Dimethyl-6- (5-methyl-3-phenyl-isoxazol-4-ylcarboxamido) -7-oxo-4-thia-1-azabicyclo [3.2.0 ] -heptane-2-carboxylic acid ( IUPAC ) Oxacillinum ( Latin )
Molecular formula	C 19 H 19 N 3 O 5 S (oxacillin) C 19 H 18 N 3 NaO 5 S · H 2 O ( monosodium salt mono hydrate )
External identifiers / databases
CAS number 66-79-5 (oxacillin) 1173-88-2 (monosodium salt) 7240-38-2 (monosodium salt monohydrate) EC number 200-635-5 ECHA InfoCard 100,000,577 PubChem 6196 ChemSpider 5961 DrugBank DB00713 Wikidata Q418725
Drug information
ATC code	J01 CF04
Drug class	Antibiotics staphylococci - penicillins
properties
Molar mass	401.44 g · mol -1
Physical state	firmly
Melting point	188 ° C (oxacillin monosodium salt monohydrate)
pK s value	2.72
solubility	Water: 27.8 mg l −1 (25 ° C)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Sodium salt monohydrate danger H and P phrases H: 315-317-319-334-335 P: 261-280-305 + 351 + 338-342 + 311
Toxicological data	1490 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Oxacillin is an antibiotic from the group of β-lactam antibiotics , which belongs to the class of isoxazolyl penicillins. It belongs to the penicillinase- resistant penicillins , the so-called staphylococcal penicillins.

The clinical area of ​​action of oxacillin is penicillinase- producing staphylococci strains. Here it serves as the key antibiotic. Nosocomial infections are, however, increasingly multi-resistant Staphylococcus aureus caused strains, one speaks in this case of O xacillin- R esistenten- S taphylococcus a ureus strains in short ORSA. The more commonly used term as methicillin-resistant Staphylococcus aureus , or MRSA for short, is synonymous. The background to these different names is the approval of methicillin in the USA and oxacillin in Europe.

Other penicillinase-resistant antibiotics are cloxacillin , dicloxacillin , flucloxacillin and methicillin , although methicillin is nowadays used neither therapeutically nor for testing sensitivity.

Trade names

• InfectoStaph (D), Stapenor Salbe ad us.vet. (Cattle) (D))

Individual evidence

1. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 1190.
2. ↑ ^{a b c} Entry on oxacillin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
3. ↑ ^{a b} Datasheet Oxacillin sodium salt monohydrate from Sigma-Aldrich , accessed on November 7, 2016 ( PDF ).
4. ↑ ABDA database (as of December 10, 2009).

Web links

• Entry on Oxacillin at Vetpharm

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !