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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++].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(C)ON=C3C4=C(F)C=CC=C4Cl)C([O-])=O.[H][C@]56SC(C)(C)[C@@H](N5C(=O)[C@H]6NC(=O)C7=C(C)ON=C7C8=C(F)C=CC=C8Cl)C([O-])=O

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 No
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23542420

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

Curator's Comment: Flucloxacillin diffuses in only small proportion into the cerebrospinal fluid of subjects whose meninges are not inflamed.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Floxapen

Approved Use

Floxapen is indicated for the treatment of infections due to sensitive Gram-positive organisms, including β-lactamase-producing staphylococci and streptococci. Typical indications include: 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.
Curative
Floxapen

Approved Use

Floxapen is indicated for the treatment of infections due to sensitive Gram-positive organisms, including β-lactamase-producing staphylococci and streptococci. Typical indications include: 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.
Curative
Floxapen

Approved Use

Floxapen is indicated for the treatment of infections due to sensitive Gram-positive organisms, including β-lactamase-producing staphylococci and streptococci. Typical indications include: 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.
Curative
Floxapen

Approved Use

Floxapen is indicated for the treatment of infections due to sensitive Gram-positive organisms, including β-lactamase-producing staphylococci and streptococci. Typical indications include: 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.
PubMed

PubMed

TitleDatePubMed
Acute adduction deficit in a 7-week-old infant.
2002 Dec
Mechanical characteristics of antibiotic-laden bone cement.
2002 Dec
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
Efficacy and safety of linezolid in the treatment of skin and soft tissue infections.
2002 Jul
Docetaxel-induced nail dystrophy.
2002 Nov
PKQuest: capillary permeability limitation and plasma protein binding - application to human inulin, dicloxacillin and ceftriaxone pharmacokinetics.
2002 Sep 26
An unusual intraorbital abscess in a neonate.
2002 Sep-Oct
How to calculate clearance of highly protein-bound drugs during continuous venovenous hemofiltration demonstrated with flucloxacillin.
2003
Staphylococcal scalded skin syndrome: diagnosis and management.
2003
Stability and in vitro efficacy of antibiotic-heparin lock solutions potentially useful for treatment of central venous catheter-related sepsis.
2003 Apr
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
Bartonella henselae infective endocarditis in north Queensland.
2003 Jan-Feb
Clinicopathological case 3: pemphigus foliaceus; bullous impetigo; subcorneal pustular dermatoses.
2003 Jul
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
A systematic review and meta-analysis of treatments for impetigo.
2003 Jun
[Diagnostic image (128). A boy who refused to walk. Spondylodiscitis LIV-LV].
2003 Mar 1
Spectrophotometric determination of flucloxacillin in pharmaceutical preparations using some nitrophenols as a complexing agent.
2003 Mar 1
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
Methicillin-resistant Staphylococcus aureus in children with cystic fibrosis: An eradication protocol.
2003 Sep
Early interventions in CF.
2004
Is the MIC useful in deciding to treat endocarditis surgically?
2004 Apr
Streptococcal necrotising fasciitis from diverse strains of Streptococcus pyogenes in tropical northern Australia: case series and comparison with the literature.
2004 Dec 16
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
Osteomyelitis of the accessory navicular bone in the foot. A case report.
2004 Jun
Dermoscopy of tungiasis.
2004 Jun
[Cutaneous nocardiosis as an opportunistic infection].
2004 Mar 13
Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates.
2004 May
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
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.
2004 Oct
Methicillin-resistant Staphylococcus aureus in Europe, 1999-2002.
2004 Sep
Osteomyelitis complicating pyomyositis in HIV disease.
2004 Sep
Determination of certain drugs in binary mixtures formulations by second derivative ratio spectrophotometry and LC.
2004 Sep
Investigation of microenvironmental factors influencing the longitudinal relaxation times of drugs and other compounds.
2004 Sep
Thoracic spondylitis from a mycotic (Streptococcus pneumoniae) aortic aneurysm: a case report.
2004 Sep 1
Staphylococcus aureus bacteremia, Australia.
2005 Apr
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

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
Flucloxacillin showed less activity, with MICs up to 32 ug/ml against of methicillin-resistant Staphylococcus aureus.
Substance Class Chemical
Created
by admin
on Fri Dec 15 21:48:45 GMT 2023
Edited
by admin
on Fri Dec 15 21:48:45 GMT 2023
Record UNII
1L80I8UP9C
Record Status Validated (UNII)
Record Version
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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
FDA UNII
1L80I8UP9C
Created by admin on Fri Dec 15 21:48:45 GMT 2023 , Edited by admin on Fri Dec 15 21:48:45 GMT 2023
PRIMARY
SMS_ID
100000086990
Created by admin on Fri Dec 15 21:48:45 GMT 2023 , Edited by admin on Fri Dec 15 21:48:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID60193184
Created by admin on Fri Dec 15 21:48:45 GMT 2023 , Edited by admin on Fri Dec 15 21:48:45 GMT 2023
PRIMARY
CAS
40182-54-5
Created by admin on Fri Dec 15 21:48:45 GMT 2023 , Edited by admin on Fri Dec 15 21:48:45 GMT 2023
PRIMARY
PUBCHEM
44250927
Created by admin on Fri Dec 15 21:48:45 GMT 2023 , Edited by admin on Fri Dec 15 21:48:45 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY