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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C19H16ClFN3O5S.Mg.8H2O
Molecular Weight 1074.155
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUCLOXACILLIN MAGNESIUM OCTAHYDRATE

SMILES

O.O.O.O.O.O.O.O.[Mg++].[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.[H][C@]56SC(C)(C)[C@@H](N5C(=O)[C@H]6NC(=O)C7=C(C)ON=C7C8=C(F)C=CC=C8Cl)C([O-])=O

InChI

InChIKey=KEPODGZDCGXBMJ-PQYXWZOCSA-L
InChI=1S/2C19H17ClFN3O5S.Mg.8H2O/c2*1-7-10(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;;;;;;;;;/h2*4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);;8*1H2/q;;+2;;;;;;;;/p-2/t2*13-,14+,17-;;;;;;;;;/m11........./s1

HIDE SMILES / InChI

Molecular Formula Mg
Molecular Weight 24.305
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Hepatitis from 5-methoxypsoralen occurring in a patient with previous flucloxacillin hepatitis.
1999 Nov
Staphylococcal submandibular lymphadentitis of childhood.
2001
Bacterial endocarditis: a rare complication following orthotopic cardiac transplantation.
2001 Apr
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
Paraplegia secondary to Burkholderia pseudomallei myelitis: a case report.
2001 Nov
3: Community-acquired pneumonia.
2002 Apr 1
Acute adduction deficit in a 7-week-old infant.
2002 Dec
Mechanical characteristics of antibiotic-laden bone cement.
2002 Dec
Efficacy and safety of linezolid in the treatment of skin and soft tissue infections.
2002 Jul
[Optimalization of antibiotic policy in the Netherlands. VII. SWAB-guidelines for antimicrobial therapy in adults patients with infectious endocarditis].
2003 Dec 6
Spectrophotometric determination of flucloxacillin in pharmaceutical preparations using some nitrophenols as a complexing agent.
2003 Mar 1
Ringworm causing childhood preseptal cellulitis.
2003 May
Panton-valentine leukocidin and staphyloccoccal skin infections in schoolchildren.
2004 Jan
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
Treatment of bullous impetigo and the staphylococcal scalded skin syndrome in infants.
2004 Jun
Dermoscopy of tungiasis.
2004 Jun
Imported cutaneous diphtheria, United Kingdom.
2004 Mar
Percutaneous closure of interatrial communications in adults - prospective embolism prevention study with two- and three-dimensional echocardiography.
2004 May 19
Investigation of microenvironmental factors influencing the longitudinal relaxation times of drugs and other compounds.
2004 Sep
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
Acute osteomyelitis and septic arthritis in children.
2005 Jan-Feb
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 Fri Dec 15 18:30:18 GMT 2023
Edited
by admin
on Fri Dec 15 18:30:18 GMT 2023
Record UNII
4Z8782KMVT
Record Status Validated (UNII)
Record Version
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Name Type Language
FLUCLOXACILLIN MAGNESIUM OCTAHYDRATE
Common Name English
FLOXACILLIN MAGNESIUM
Common Name English
Magnesium bis[(2S,5R,6R)-6-[[[3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate] octahydrate
Common Name English
FLUCLOXACILLIN MAGNESIUM OCTAHYDRATE [EP MONOGRAPH]
Common Name 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.)), MAGNESIUM SALT, OCTAHYDRATE
Common Name English
FLOXACILLIN MAGNESIUM OCTAHYDRATE
Common Name English
FLUCLOXACILLIN MAGNESIUM
Common Name English
Code System Code Type Description
SMS_ID
100000164775
Created by admin on Fri Dec 15 18:30:18 GMT 2023 , Edited by admin on Fri Dec 15 18:30:18 GMT 2023
PRIMARY
FDA UNII
4Z8782KMVT
Created by admin on Fri Dec 15 18:30:18 GMT 2023 , Edited by admin on Fri Dec 15 18:30:18 GMT 2023
PRIMARY
PUBCHEM
76969488
Created by admin on Fri Dec 15 18:30:18 GMT 2023 , Edited by admin on Fri Dec 15 18:30:18 GMT 2023
PRIMARY
EVMPD
SUB179354
Created by admin on Fri Dec 15 18:30:18 GMT 2023 , Edited by admin on Fri Dec 15 18:30:18 GMT 2023
PRIMARY
EVMPD
SUB02206MIG
Created by admin on Fri Dec 15 18:30:18 GMT 2023 , Edited by admin on Fri Dec 15 18:30:18 GMT 2023
PRIMARY
RXCUI
235825
Created by admin on Fri Dec 15 18:30:18 GMT 2023 , Edited by admin on Fri Dec 15 18:30:18 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY