Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H16ClFN3O5S.Na |
Molecular Weight | 475.854 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[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=OTEANHMVDHZOPB-SLINCCQESA-M
InChI=1S/C19H17ClFN3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1
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 |
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Target ID: CHEMBL2363021 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6335600 |
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Target ID: CHEMBL2362973 Sources: https://www.ncbi.nlm.nih.gov/pubmed/318800 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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. |
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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 |
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How to calculate clearance of highly protein-bound drugs during continuous venovenous hemofiltration demonstrated with flucloxacillin. | 2003 |
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Necrotising fasciitis in neonates: a multidisciplinary approach. | 2003 Aug 22 |
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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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Clinicopathological case 3: pemphigus foliaceus; bullous impetigo; subcorneal pustular dermatoses. | 2003 Jul |
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The pharmacokinetics of the interstitial space in humans. | 2003 Jul 30 |
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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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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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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 |
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Methicillin-resistant Staphylococcus aureus in children with cystic fibrosis: An eradication protocol. | 2003 Sep |
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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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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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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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Effects of duplicate and screening isolates on surveillance of community and hospital antibiotic resistance. | 2004 Jul |
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Treatment of bullous impetigo and the staphylococcal scalded skin syndrome in infants. | 2004 Jun |
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Osteomyelitis of the accessory navicular bone in the foot. A case report. | 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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Methicillin-resistant Staphylococcus aureus in Europe, 1999-2002. | 2004 Sep |
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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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Flucloxacillin associated neutropenia in children treated for bone and joint infections. | 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
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.
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DTXSID6045115
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1847-24-1
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23667629
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100000086971
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277175
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235750
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217-428-0
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05F65O42VK
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ACTIVE MOIETY
SUBSTANCE RECORD