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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17ClFN3O5S
Molecular Weight 453.872
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUCLOXACILLIN

SMILES

CC1=C(C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)C(=NO1)C4=C(Cl)C=CC=C4F

InChI

InChIKey=UIOFUWFRIANQPC-JKIFEVAISA-N
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

HIDE SMILES / InChI

Description

Flucloxacillin is an isoxazolyl penicillin of the β-lactam group of antibiotics, which exerts a bactericidal effect upon many Gram-positive organisms including β-lactamase-producing staphylococci and streptococci. While no longer used in the United States, Flucloxacillin is supplied under a variety of trade names in other countries, including Floxapen, Flopen, Staphylex. Floxapen is indicated for the treatment of infections due to sensitive Gram-positive organisms, including β-lactamase-producing staphylococci and streptococci. Typical indications including, skin and soft tissue infections; respiratory tract infections; other infections caused by floxapen-sensitive organisms, like example, osteomyelitis, urinary tract infection, septicaemia, endocarditis. Floxapen is also indicated for use as a prophylactic agent during major surgical procedures when appropriate; for example cardiothoracic and orthopaedic surgery. Flucloxacillin, by its action on the synthesis of the bacterial wall, exerts a bactericidal effect on streptococci except those of group D (Enterococcus faecalis) staphylococci. It is not active against methicillin-resistant staphylococci. There is evidence that the risk of flucloxacillin induced liver injury is increased in subjects carrying the HLA-B*5701 allele. Despite this strong association, only 1 in 500-1000 carriers will develop liver injury. Consequently, the positive predictive value of testing the HLA-B*5701 allele for liver injury is very low (0.12%) and routine screening for this allele is not recommended. Flucloxacillin diffuses well into most tissue. Specifically, active concentrations of flucloxacillin have been recovered in bones: 11.6 mg/L (compact bone) and 15.6 mg/L (spongy bone), with a mean serum level of 8.9 mg/L. Flucloxacillin diffuses in only small proportion into the cerebrospinal fluid of subjects whose meninges are not inflamed. It is also excreted in small quantities in mother's milk. In normal subjects approximately 10% of the flucloxacillin administered is metabolised to penicilloic acid. The elimination half-life of flucloxacillin is in the order of 53 minutes.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Economic evaluation of linezolid, flucloxacillin and vancomycin in the empirical treatment of cellulitis in UK hospitals: a decision analytical model.
2001 Dec
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
Staphylococcus aureus bacteremia, Australia.
2005 Apr
Flucloxacillin-induced aplastic anaemia and liver failure.
2005 Apr
Quantitative determination method for trace amount of penicillin contaminants in commercially available drug product by HPLC coupled with tandem mass spectrometry.
2005 Feb
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland.
2005 Feb
An isocratic ion exchange HPLC method for the simultaneous determination of flucloxacillin and amoxicillin in a pharmaceutical formulation for injection.
2005 Feb 23
Cutaneous adverse drug reaction to oral chlorphenamine detected with patch testing.
2005 Jan
Acute osteomyelitis and septic arthritis in children.
2005 Jan-Feb
Bactericidal activity of flucloxacillin against Staphylococcus aureus in primary keratinocyte cultures of lesional and unaffected skin of patients suffering from atopic dermatitis.
2005 Mar
Flucloxacillin alone or combined with benzylpenicillin to treat lower limb cellulitis: a randomised controlled trial.
2005 May
The role of antibiotic prophylaxis in clean incised hand injuries: a prospective randomized placebo controlled double blind trial.
2005 May
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Usual adult dosage (including elderly patients): Oral - 250 mg four times a day. Osteomyelitis, endocarditis - Up to 8 g daily, in divided doses six to eight hourly. Usual children's dosage: 2-10 years: half adult dose. Under 2 years: quarter adult dose.
Route of Administration: Oral
In Vitro Use Guide
Flucloxacillin showed less activity, with MICs up to 32 ug/ml against of methicillin-resistant Staphylococcus aureus.
Name Type Language
FLUCLOXACILLIN
INN   MART.   WHO-DD  
INN  
Official Name English
BRL 2039
Code English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((3-(2-CHLORO-6-FLUOROPHENYL)-5-METHYL-4-ISOXAZOLYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, (2S(2.ALPHA.,5.ALPHA.,6.BETA.))
Common Name English
FLOXACILLIN [USAN]
Common Name English
BRL-2039
Code English
FLUCLOXACILLIN [INN]
Common Name English
FLOXACILLIN
MI   USAN  
USAN  
Official Name English
FLOXACILLIN [MI]
Common Name English
6-(3-(2-CHLORO-6-FLUOROPHENYL)-5-METHYL-4-ISOXAZOLECARBOXAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
FLUCLOXACILLIN [WHO-DD]
Common Name English
FLUCLOXACILLIN [MART.]
Common Name English
3-(2-CHLORO-6-FLUOROPHENYL)-5-METHYL-4-ISOXAZOLYLPENICILLIN
Common Name English
Classification Tree Code System Code
WHO-VATC QJ51CF05
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
WHO-ATC J01CF05
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
WHO-VATC QJ01CF05
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
LIVERTOX 419
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
Code System Code Type Description
PUBCHEM
21319
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY SWITZERF
LactMed
5250-39-5
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
RXCUI
4448
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY RxNorm
CAS
5250-39-5
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
EPA CompTox
5250-39-5
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
ChEMBL
CHEMBL222645
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
INN
2308
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
MERCK INDEX
M5413
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY Merck Index
MESH
D005436
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
ECHA (EC/EINECS)
226-051-0
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
NCI_THESAURUS
C80591
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
WIKIPEDIA
FLUCLOXACILLIN
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
DRUG BANK
DB00301
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY
EVMPD
SUB07673MIG
Created by admin on Tue Mar 06 11:20:24 UTC 2018 , Edited by admin on Tue Mar 06 11:20:24 UTC 2018
PRIMARY