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

Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16ClFN3O5S.Na.H2O
Molecular Weight 493.869
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUCLOXACILLIN SODIUM MONOHYDRATE

SMILES

O.[Na+].[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

InChI

InChIKey=PARMJFIQRZRMHG-VICXVTCVSA-M
InChI=1S/C19H17ClFN3O5S.Na.H2O/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);;1H2/q;+1;/p-1/t13-,14+,17-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula C19H17ClFN3O5S
Molecular Weight 453.872
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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
Hepatitis from 5-methoxypsoralen occurring in a patient with previous flucloxacillin hepatitis.
1999 Nov
Staphylococcal submandibular lymphadentitis of childhood.
2001
Percutaneous treatment of chronic MRSA osteomyelitis with a novel plant-derived antiseptic.
2001
Economic evaluation of linezolid, flucloxacillin and vancomycin in the empirical treatment of cellulitis in UK hospitals: a decision analytical model.
2001 Dec
Spectrophotometric determination of ampicillin, dicluxacillin, flucloxacillin and amoxicillin antibiotic drugs: ion-pair formation with molybdenum and thiocyanate.
2001 Feb
Factors compromising antibiotic activity against biofilms of Staphylococcus epidermidis.
2001 Jan
Indirect cytotoxicity of flucloxacillin toward human biliary epithelium via metabolite formation in hepatocytes.
2001 Jun
Spinal osteomyelitis and diskitis: a rare complication following orthotopic heart transplantation.
2001 Nov
Paraplegia secondary to Burkholderia pseudomallei myelitis: a case report.
2001 Nov
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
Re: Conservative Management of Gradenigo Syndrome in a Child.
2002 Jan 11
Staphylococcus aureus endocarditis in preterm neonates.
2002 Jul
Selective spectrophotometric determination of phenolic beta-lactam antibiotics.
2002 Jun 15
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
[Optimalization of antibiotic policy in the Netherlands. VII. SWAB-guidelines for antimicrobial therapy in adults patients with infectious endocarditis].
2003 Dec 6
Spectrophotometric determination of flucloxacillin in pharmaceutical preparations using some nitrophenols as a complexing agent.
2003 Mar 1
Is the MIC useful in deciding to treat endocarditis surgically?
2004 Apr
[Diagnostic image (185). A man with a pimple on the upper lip. Carbuncle of the upper lip].
2004 Apr 17
[Diagnostic image (202). A newborn with subfebrile temperature and skin lesions. Staphylococcal scalded skin syndrome].
2004 Aug 14
Streptococcal necrotising fasciitis from diverse strains of Streptococcus pyogenes in tropical northern Australia: case series and comparison with the literature.
2004 Dec 16
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
Activity of nadifloxacin (OPC-7251) and seven other antimicrobial agents against aerobic and anaerobic Gram-positive bacteria isolated from bacterial skin infections.
2004 Oct
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
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
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 18:57:10 GMT 2023
Edited
by admin
on Fri Dec 15 18:57:10 GMT 2023
Record UNII
LMG7C674WJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FLUCLOXACILLIN SODIUM MONOHYDRATE
MI  
Common Name English
STAPHYLEX
Brand Name English
FLOXAPEN
Brand Name English
FLUCLOXACILLIN SODIUM
EP   JAN  
Common Name English
FLUCLOXACILLIN SODIUM [JAN]
Common Name English
FLUCLOXACILLIN SODIUM MONOHYDRATE [MI]
Common Name English
FLUCLOXACILLIN SODIUM [EP MONOGRAPH]
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-, SODIUM SALT MONOHYDRATE (2S(2.ALPHA.,5.ALPHA.,6.BETA.))
Common Name English
CULPEN
Brand Name English
LADROPEN
Brand Name English
ABBOFLOX
Brand Name English
STAFOXIL
Brand Name English
SODIUM (2S,5R,6R)-6-(((3-(2-CHLORO-6-FLUOROPHENYL)-5-METHYLISOXAZOL-4-YL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE MONOHYDRATE
Systematic Name English
STAPHLIPEN
Brand Name English
Code System Code Type Description
EVMPD
SUB02207MIG
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
SMS_ID
100000128057
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
CAS
34214-51-2
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
RXCUI
1309402
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY RxNorm
CHEBI
31615
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID1046477
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
CHEBI
52040
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
PUBCHEM
23706211
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
DRUG BANK
DBSALT000345
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
FDA UNII
LMG7C674WJ
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
EVMPD
SUB34711
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL222645
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
CHEBI
5098
Created by admin on Fri Dec 15 18:57:10 GMT 2023 , Edited by admin on Fri Dec 15 18:57:10 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY