U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Hepatitis from 5-methoxypsoralen occurring in a patient with previous flucloxacillin hepatitis.
1999 Nov
Sub-inhibitory concentrations of vancomycin prevent quinolone-resistance in a penicillin-resistant isolate of Streptococcus pneumoniae.
2001
Percutaneous treatment of chronic MRSA osteomyelitis with a novel plant-derived antiseptic.
2001
Bacterial endocarditis: a rare complication following orthotopic cardiac transplantation.
2001 Apr
Supraglottitis complicated by mediastinitis.
2001 Apr
Fulminant orbital cellulitis with complete loss of vision.
2001 Aug
Pyrocatechol violet in pharmaceutical analysis. Part I. A spectrophotometric method for the determination of some beta-lactam antibiotics in pure and in pharmaceutical dosage forms.
2001 Mar
Complicated infective endocarditis necessitating ICU admission: clinical course and prognosis.
2002 Apr
3: Community-acquired pneumonia.
2002 Apr 1
Cervical discitis in a patient with an oesophageal stent for carcinoma.
2002 Dec
Localised necrosis of scrotum (Fournier's gangrene) in a spinal cord injury patient - a case report.
2002 Dec 5
Chronic relapsing salmonella osteomyelitis in an immunocompetent patient: case report and literature review.
2002 Jan
Efficacy and safety of linezolid in the treatment of skin and soft tissue infections.
2002 Jul
Staphylococcus aureus endocarditis in preterm neonates.
2002 Jul
Mitral valve endocarditis in hypertrophic cardiomyopathy: case report and literature review.
2002 Jun
Selective spectrophotometric determination of phenolic beta-lactam antibiotics.
2002 Jun 15
Catheter-related epidural abscesses -- don't wait for neurological deficits.
2002 May
Home intravenous antimicrobial service--twelve months experience in Christchurch.
2002 May 10
5: Hospital-in-the-home treatment of infectious diseases.
2002 May 6
Docetaxel-induced nail dystrophy.
2002 Nov
Necrotising fasciitis in neonates: a multidisciplinary approach.
2003 Aug 22
Unilateral submandibular suppurative sialadenitis in a premature infant.
2003 Dec
[Optimalization of antibiotic policy in the Netherlands. VII. SWAB-guidelines for antimicrobial therapy in adults patients with infectious endocarditis].
2003 Dec 6
Ringworm causing childhood preseptal cellulitis.
2003 May
Small colony variants of Staphylococcus aureus and pacemaker-related infection.
2003 Oct
The use of prophylactic flucloxacillin in treatment of open fractures of the distal phalanx within an accident and emergency department: a double-blind randomized placebo-controlled trial.
2003 Oct
Early interventions in CF.
2004
[Diagnostic image (185). A man with a pimple on the upper lip. Carbuncle of the upper lip].
2004 Apr 17
Pharmacokinetics of intravenous flucloxacillin and amoxicillin in neonatal and infant cardiopulmonary bypass surgery.
2004 Feb
Purpura fulminans due to E. coli septicemia.
2004 Feb 16
Congenital cyanotic heart disease and headache.
2004 Jan-Feb
Acute and clinically relevant drug-induced liver injury: a population based case-control study.
2004 Jul
Effects of duplicate and screening isolates on surveillance of community and hospital antibiotic resistance.
2004 Jul
Imported cutaneous diphtheria, United Kingdom.
2004 Mar
[Cutaneous nocardiosis as an opportunistic infection].
2004 Mar 13
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.
2004 Oct
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 Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
WHO-ATC J01CF05
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
WHO-VATC QJ01CF05
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
NCI_THESAURUS C1500
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
LIVERTOX 419
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
Code System Code Type Description
PUBCHEM
21319
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
LactMed
5250-39-5
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
RXCUI
4448
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY RxNorm
CAS
5250-39-5
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
EPA CompTox
5250-39-5
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
ChEMBL
CHEMBL222645
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
INN
2308
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
MERCK INDEX
M5413
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY Merck Index
MESH
D005436
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
ECHA (EC/EINECS)
226-051-0
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
NCI_THESAURUS
C80591
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
WIKIPEDIA
FLUCLOXACILLIN
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
DRUG BANK
DB00301
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY
EVMPD
SUB07673MIG
Created by admin on Mon Oct 21 19:48:58 UTC 2019 , Edited by admin on Mon Oct 21 19:48:58 UTC 2019
PRIMARY