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

[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=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

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

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
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
Supraglottitis complicated by mediastinitis.
2001 Apr
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
[Microbiological and immunological monitoring in polyarticular rheumatoid arthritis after total joint replacement].
2001 Feb 9
Factors compromising antibiotic activity against biofilms of Staphylococcus epidermidis.
2001 Jan
[Fever and vesiculopapular exanthema due to infection with Rickettsia africae after a sojourn in South Africa].
2001 Jan 20
Cervical discitis in a patient with an oesophageal stent for carcinoma.
2002 Dec
Home intravenous antimicrobial service--twelve months experience in Christchurch.
2002 May 10
5: Hospital-in-the-home treatment of infectious diseases.
2002 May 6
Post-partum toxic shock syndrome due to an unexpected source.
2002 Sep
Unilateral submandibular suppurative sialadenitis in a premature infant.
2003 Dec
The pharmacokinetics of the interstitial space in humans.
2003 Jul 30
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
[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
Pharmacokinetics of intravenous flucloxacillin and amoxicillin in neonatal and infant cardiopulmonary bypass surgery.
2004 Feb
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
Osteomyelitis of the accessory navicular bone in the foot. A case report.
2004 Jun
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
Staphylococcus aureus bacteremia, Australia.
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
Flucloxacillin associated neutropenia in children treated for bone and joint infections.
2005 Jan-Feb
Flucloxacillin alone or combined with benzylpenicillin to treat lower limb cellulitis: a randomised controlled 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 Sat Dec 16 17:41:14 GMT 2023
Edited
by admin
on Sat Dec 16 17:41:14 GMT 2023
Record UNII
43B2M34G2V
Record Status Validated (UNII)
Record Version
  • Download
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 [MART.]
Common Name English
3-(2-CHLORO-6-FLUOROPHENYL)-5-METHYL-4-ISOXAZOLYLPENICILLIN
Common Name English
Flucloxacillin [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ51CF05
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
WHO-ATC J01CF05
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
WHO-VATC QJ01CF05
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
NCI_THESAURUS C1500
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
LIVERTOX 419
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
Code System Code Type Description
FDA UNII
43B2M34G2V
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
PUBCHEM
21319
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
DRUG CENTRAL
1183
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
RXCUI
4448
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY RxNorm
CAS
5250-39-5
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023056
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL222645
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
LACTMED
Floxacillin
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
INN
2308
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
MERCK INDEX
m5413
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY Merck Index
MESH
D005436
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
ECHA (EC/EINECS)
226-051-0
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
NCI_THESAURUS
C80591
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
WIKIPEDIA
FLUCLOXACILLIN
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
DRUG BANK
DB00301
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
CHEBI
5098
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
SMS_ID
100000092666
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
EVMPD
SUB07673MIG
Created by admin on Sat Dec 16 17:41:15 GMT 2023 , Edited by admin on Sat Dec 16 17:41:15 GMT 2023
PRIMARY
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