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
[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
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 |
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 |
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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. |
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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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Sub-inhibitory concentrations of vancomycin prevent quinolone-resistance in a penicillin-resistant isolate of Streptococcus pneumoniae. | 2001 |
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Percutaneous treatment of chronic MRSA osteomyelitis with a novel plant-derived antiseptic. | 2001 |
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Supraglottitis complicated by mediastinitis. | 2001 Apr |
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The efficacy of continuous infusion flucloxacillin in home therapy for serious staphylococcal infections and cellulitis. | 2001 Aug |
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Spectrophotometric determination of ampicillin, dicluxacillin, flucloxacillin and amoxicillin antibiotic drugs: ion-pair formation with molybdenum and thiocyanate. | 2001 Feb |
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[Microbiological and immunological monitoring in polyarticular rheumatoid arthritis after total joint replacement]. | 2001 Feb 9 |
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Factors compromising antibiotic activity against biofilms of Staphylococcus epidermidis. | 2001 Jan |
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[Fever and vesiculopapular exanthema due to infection with Rickettsia africae after a sojourn in South Africa]. | 2001 Jan 20 |
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Cervical discitis in a patient with an oesophageal stent for carcinoma. | 2002 Dec |
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Home intravenous antimicrobial service--twelve months experience in Christchurch. | 2002 May 10 |
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5: Hospital-in-the-home treatment of infectious diseases. | 2002 May 6 |
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Post-partum toxic shock syndrome due to an unexpected source. | 2002 Sep |
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Unilateral submandibular suppurative sialadenitis in a premature infant. | 2003 Dec |
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The pharmacokinetics of the interstitial space in humans. | 2003 Jul 30 |
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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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[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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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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Osteomyelitis of the accessory navicular bone in the foot. A case report. | 2004 Jun |
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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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Staphylococcus aureus bacteremia, Australia. | 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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Flucloxacillin associated neutropenia in children treated for bone and joint infections. | 2005 Jan-Feb |
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Flucloxacillin alone or combined with benzylpenicillin to treat lower limb cellulitis: a randomised controlled 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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Record UNII |
43B2M34G2V
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Record Status |
Validated (UNII)
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419
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