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
SMILES
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
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
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
Title | Date | PubMed |
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Acute adduction deficit in a 7-week-old infant. | 2002 Dec |
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Mechanical characteristics of antibiotic-laden bone cement. | 2002 Dec |
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Cervical discitis in a patient with an oesophageal stent for carcinoma. | 2002 Dec |
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Localised necrosis of scrotum (Fournier's gangrene) in a spinal cord injury patient - a case report. | 2002 Dec 5 |
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Staphylococcus septicaemia and massive vulvar oedema in pregnancy. | 2002 Nov |
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Docetaxel-induced nail dystrophy. | 2002 Nov |
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Post-partum toxic shock syndrome due to an unexpected source. | 2002 Sep |
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An unusual intraorbital abscess in a neonate. | 2002 Sep-Oct |
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Staphylococcal scalded skin syndrome: diagnosis and management. | 2003 |
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Stability and in vitro efficacy of antibiotic-heparin lock solutions potentially useful for treatment of central venous catheter-related sepsis. | 2003 Apr |
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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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Osteomyelitis following a haematoma block. | 2003 Jan |
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A systematic review and meta-analysis of treatments for impetigo. | 2003 Jun |
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[Diagnostic image (128). A boy who refused to walk. Spondylodiscitis LIV-LV]. | 2003 Mar 1 |
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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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Ringworm causing childhood preseptal cellulitis. | 2003 May |
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Small colony variants of Staphylococcus aureus and pacemaker-related infection. | 2003 Oct |
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Early interventions in CF. | 2004 |
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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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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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Panton-valentine leukocidin and staphyloccoccal skin infections in schoolchildren. | 2004 Jan |
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Congenital cyanotic heart disease and headache. | 2004 Jan-Feb |
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Acute and clinically relevant drug-induced liver injury: a population based case-control study. | 2004 Jul |
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Treatment of bullous impetigo and the staphylococcal scalded skin syndrome in infants. | 2004 Jun |
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Dermoscopy of tungiasis. | 2004 Jun |
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Imported cutaneous diphtheria, United Kingdom. | 2004 Mar |
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[Cutaneous nocardiosis as an opportunistic infection]. | 2004 Mar 13 |
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Modulation of beta-lactam resistance in Staphylococcus aureus by catechins and gallates. | 2004 May |
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Percutaneous closure of interatrial communications in adults - prospective embolism prevention study with two- and three-dimensional echocardiography. | 2004 May 19 |
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Allogenic blood transfusion does not predispose to infection after cardiac surgery. | 2004 Nov |
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A randomized clinical trial to compare fleroxacin-rifampicin with flucloxacillin or vancomycin for the treatment of staphylococcal infection. | 2004 Nov 1 |
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Therapeutic impact of percutaneous spinal biopsy in spinal infection. | 2004 Oct |
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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 |
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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 |
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Investigation of microenvironmental factors influencing the longitudinal relaxation times of drugs and other compounds. | 2004 Sep |
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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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Flucloxacillin-induced aplastic anaemia and liver failure. | 2005 Apr |
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Quantitative determination method for trace amount of penicillin contaminants in commercially available drug product by HPLC coupled with tandem mass spectrometry. | 2005 Feb |
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Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland. | 2005 Feb |
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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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Acute osteomyelitis and septic arthritis in children. | 2005 Jan-Feb |
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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 |
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Flucloxacillin alone or combined with benzylpenicillin to treat lower limb cellulitis: a randomised controlled trial. | 2005 May |
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The role of antibiotic prophylaxis in clean incised hand injuries: a prospective randomized placebo controlled double blind trial. | 2005 May |
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
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QJ51CF05
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WHO-ATC |
J01CF05
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WHO-VATC |
QJ01CF05
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NCI_THESAURUS |
C1500
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LIVERTOX |
419
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Code System | Code | Type | Description | ||
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21319
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5250-39-5
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PRIMARY | |||
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4448
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PRIMARY | RxNorm | ||
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5250-39-5
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PRIMARY | |||
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5250-39-5
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PRIMARY | |||
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CHEMBL222645
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2308
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PRIMARY | |||
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M5413
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D005436
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226-051-0
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C80591
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FLUCLOXACILLIN
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DB00301
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PRIMARY | |||
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SUB07673MIG
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)