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

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C19H16ClFN3O5S.Mg
Molecular Weight 930.033
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUCLOXACILLIN MAGNESIUM ANHYDROUS

SMILES

[Mg++].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.CC5=C(C(=O)N[C@H]6[C@H]7SC(C)(C)[C@@H](N7C6=O)C([O-])=O)C(=NO5)C8=C(Cl)C=CC=C8F

InChI

InChIKey=LYQDZCZZTPNAIP-VZHMHXRYSA-L
InChI=1S/2C19H17ClFN3O5S.Mg/c2*1-7-10(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;/h2*4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);/q;;+2/p-2/t2*13-,14+,17-;/m11./s1

HIDE SMILES / InChI

Molecular Formula C19H16ClFN3O5S
Molecular Weight 452.864
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Mg
Molecular Weight 24.305
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Percutaneous treatment of chronic MRSA osteomyelitis with a novel plant-derived antiseptic.
2001
[Chronic fistulating wound infection after Lichtenstein repair of inguinal hernia, caused by a small colony variant of Staphylococcus aureus].
2001 Apr
Supraglottitis complicated by mediastinitis.
2001 Apr
Fulminant orbital cellulitis with complete loss of vision.
2001 Aug
The efficacy of continuous infusion flucloxacillin in home therapy for serious staphylococcal infections and cellulitis.
2001 Aug
Spectrophotometric determination of ampicillin, dicluxacillin, flucloxacillin and amoxicillin antibiotic drugs: ion-pair formation with molybdenum and thiocyanate.
2001 Feb
Indirect cytotoxicity of flucloxacillin toward human biliary epithelium via metabolite formation in hepatocytes.
2001 Jun
Management of extravasation injuries.
2001 May
3: Community-acquired pneumonia.
2002 Apr 1
Cervical discitis in a patient with an oesophageal stent for carcinoma.
2002 Dec
The role of the Australian Adverse Drug Reactions Advisory Committee (ADRAC) in monitoring drug safety.
2002 Dec 27
Staphylococcus aureus endocarditis in preterm neonates.
2002 Jul
Catheter-related epidural abscesses -- don't wait for neurological deficits.
2002 May
An unusual intraorbital abscess in a neonate.
2002 Sep-Oct
Unilateral submandibular suppurative sialadenitis in a premature infant.
2003 Dec
Bartonella henselae infective endocarditis in north Queensland.
2003 Jan-Feb
Clinicopathological case 3: pemphigus foliaceus; bullous impetigo; subcorneal pustular dermatoses.
2003 Jul
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
Panton-valentine leukocidin and staphyloccoccal skin infections in schoolchildren.
2004 Jan
Acute and clinically relevant drug-induced liver injury: a population based case-control study.
2004 Jul
Treatment of bullous impetigo and the staphylococcal scalded skin syndrome in infants.
2004 Jun
Osteomyelitis of the accessory navicular bone in the foot. A case report.
2004 Jun
[Cutaneous nocardiosis as an opportunistic infection].
2004 Mar 13
Percutaneous closure of interatrial communications in adults - prospective embolism prevention study with two- and three-dimensional echocardiography.
2004 May 19
Allogenic blood transfusion does not predispose to infection after cardiac surgery.
2004 Nov
Therapeutic impact of percutaneous spinal biopsy in spinal infection.
2004 Oct
Methicillin-resistant Staphylococcus aureus in Europe, 1999-2002.
2004 Sep
Thoracic spondylitis from a mycotic (Streptococcus pneumoniae) aortic aneurysm: a case report.
2004 Sep 1
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
Flucloxacillin associated neutropenia in children treated for bone and joint infections.
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.
Substance Class Chemical
Created
by admin
on Tue Oct 22 13:27:08 UTC 2019
Edited
by admin
on Tue Oct 22 13:27:08 UTC 2019
Record UNII
1L80I8UP9C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUCLOXACILLIN MAGNESIUM ANHYDROUS
Common Name 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-, MAGNESIUM COMPLEX, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-
Common Name English
FLUCLOXACILLIN MAGNESIUM [WHO-DD]
Common Name 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.)), MAGNESIUM SALT
Common Name English
FLOXACILLIN MAGNESIUM ANHYDROUS
Common Name English
Code System Code Type Description
EPA CompTox
40182-54-5
Created by admin on Tue Oct 22 13:27:08 UTC 2019 , Edited by admin on Tue Oct 22 13:27:08 UTC 2019
PRIMARY
CAS
40182-54-5
Created by admin on Tue Oct 22 13:27:08 UTC 2019 , Edited by admin on Tue Oct 22 13:27:08 UTC 2019
PRIMARY
PUBCHEM
44250927
Created by admin on Tue Oct 22 13:27:08 UTC 2019 , Edited by admin on Tue Oct 22 13:27:08 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY