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
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
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 |
DescriptionSources: https://www.medicines.org.uk/emc/medicine/20393Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23542420
Sources: https://www.medicines.org.uk/emc/medicine/20393
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
Sources: https://www.medicines.org.uk/emc/medicine/20393
Curator's Comment: Flucloxacillin diffuses in only small proportion into the cerebrospinal fluid of subjects whose meninges are not inflamed.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363021 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6335600 |
|||
Target ID: CHEMBL2362973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/318800 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Floxapen Approved UseFloxapen 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 UseFloxapen 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 UseFloxapen 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 UseFloxapen 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
Title | Date | PubMed |
---|---|---|
Hepatitis from 5-methoxypsoralen occurring in a patient with previous flucloxacillin hepatitis. | 1999 Nov |
|
Staphylococcal submandibular lymphadentitis of childhood. | 2001 |
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Percutaneous treatment of chronic MRSA osteomyelitis with a novel plant-derived antiseptic. | 2001 |
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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 |
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Factors compromising antibiotic activity against biofilms of Staphylococcus epidermidis. | 2001 Jan |
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Indirect cytotoxicity of flucloxacillin toward human biliary epithelium via metabolite formation in hepatocytes. | 2001 Jun |
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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 |
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Re: Conservative Management of Gradenigo Syndrome in a Child. | 2002 Jan 11 |
|
Staphylococcus aureus endocarditis in preterm neonates. | 2002 Jul |
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Selective spectrophotometric determination of phenolic beta-lactam antibiotics. | 2002 Jun 15 |
|
Catheter-related epidural abscesses -- don't wait for neurological deficits. | 2002 May |
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An unusual intraorbital abscess in a neonate. | 2002 Sep-Oct |
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Unilateral submandibular suppurative sialadenitis in a premature infant. | 2003 Dec |
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[Optimalization of antibiotic policy in the Netherlands. VII. SWAB-guidelines for antimicrobial therapy in adults patients with infectious endocarditis]. | 2003 Dec 6 |
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Spectrophotometric determination of flucloxacillin in pharmaceutical preparations using some nitrophenols as a complexing agent. | 2003 Mar 1 |
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Is the MIC useful in deciding to treat endocarditis surgically? | 2004 Apr |
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[Diagnostic image (185). A man with a pimple on the upper lip. Carbuncle of the upper lip]. | 2004 Apr 17 |
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[Diagnostic image (202). A newborn with subfebrile temperature and skin lesions. Staphylococcal scalded skin syndrome]. | 2004 Aug 14 |
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Streptococcal necrotising fasciitis from diverse strains of Streptococcus pyogenes in tropical northern Australia: case series and comparison with the literature. | 2004 Dec 16 |
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Pharmacokinetics of intravenous flucloxacillin and amoxicillin in neonatal and infant cardiopulmonary bypass surgery. | 2004 Feb |
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Purpura fulminans due to E. coli septicemia. | 2004 Feb 16 |
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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 |
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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 |
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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 |
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Staphylococcus aureus bacteremia, Australia. | 2005 Apr |
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An isocratic ion exchange HPLC method for the simultaneous determination of flucloxacillin and amoxicillin in a pharmaceutical formulation for injection. | 2005 Feb 23 |
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Cutaneous adverse drug reaction to oral chlorphenamine detected with patch testing. | 2005 Jan |
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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
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/medicine/20393
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=6237606
Flucloxacillin showed less activity, with MICs up to 32 ug/ml against of methicillin-resistant Staphylococcus aureus.
Substance Class |
Chemical
Created
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Edited
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Record UNII |
LMG7C674WJ
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Record Status |
Validated (UNII)
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