Flucloxacillin

Flucloxacillin
Clinical data
Trade names	Floxapen, others
Other names	BRL-2039
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth, intramuscular, intravenous, intrapleural, intraarticular
ATC code	J01CF05 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); NZ: Prescription only; UK: POM (Prescription only); EU: Rx-only;
Pharmacokinetic data
Bioavailability	50–70%
Metabolism	Liver
Elimination half-life	0.75–1 hour
Excretion	Kidney
Identifiers
	IUPAC name (2S,5R,6R)-6-({[3-(2-chloro-5-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	5250-39-5 ;
PubChem CID	21319;
IUPHAR/BPS	10910;
DrugBank	DB00301;
ChemSpider	20037;
UNII	43B2M34G2V;
KEGG	D04196;
ChEBI	CHEBI:5098;
ChEMBL	ChEMBL222645;
CompTox Dashboard (EPA)	DTXSID8023056 ;
ECHA InfoCard	100.023.683
Chemical and physical data
Formula	C19H17ClFN3O5S
Molar mass	453.87 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1c(F)cccc1Cl)C)[C@H]4SC3(C)C;
	InChI InChI=1S/C19H17ClFN3O5S/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28)/t13-,14+,17-/m1/s1 ; Key:UIOFUWFRIANQPC-JKIFEVAISA-N ;
	(verify)

Flucloxacillin, also known as floxacillin, is an antibiotic used to treat skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone. It may be used together with other medications to treat pneumonia, and endocarditis. It may also be used prior to surgery to prevent Staphylococcus infections. It is not effective against methicillin-resistant Staphylococcus aureus (MRSA). It is taken by mouth or given by injection into a vein or muscle.

Common side effects include an upset stomach. Other side effects may include muscle or joint pains, shortness of breath, and liver problems. It appears to be safe during pregnancy and breastfeeding. It should not be used in those who are allergic to penicillin. It is a narrow-spectrum beta-lactam antibiotic of the penicillin class. It is similar in effect to cloxacillin and dicloxacillin, being active against penicillinase forming bacteria.

Flucloxacillin was patented in 1961.

Flucloxacillin is not available in the United States.