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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H17F2N6O7S2.Na
Molecular Weight 518.448
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLOMOXEF SODIUM

SMILES

[Na+].CO[C@]1(NC(=O)CSC(F)F)[C@H]2OCC(CSC3=NN=NN3CCO)=C(N2C1=O)C([O-])=O

InChI

InChIKey=PPPZBOLFWGINKN-YLCXCWDSSA-M
InChI=1S/C15H18F2N6O7S2.Na/c1-29-15(18-8(25)6-31-13(16)17)11(28)23-9(10(26)27)7(4-30-12(15)23)5-32-14-19-20-21-22(14)2-3-24;/h12-13,24H,2-6H2,1H3,(H,18,25)(H,26,27);/q;+1/p-1/t12-,15+;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H17F2N6O7S2
Molecular Weight 495.458
Charge -1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Flomoxef is a cephamycin antibiotic with a difluoromethylthio-acetamido group at the 7-beta position of the cephem nucleus, commonly used for postoperative prophylaxis. Flomoxef has activity against epidermides, streptococci, propionibacteria, and both methicillin-resistant and -susceptible Staphylococcus aureus. Flomoxef exhibits a broad spectrum of antibacterial activity against G(+), G(-) and even anaerobes such as Staphylococcus sp., Escherichia coli, and Bacteroides sp., and it can be used singly to treat infection caused by aerobes and anaerobes (Mixed infection) effectively. Flomoxef belongs to the cephamycin, so it is very stable against β-lactamase as well as Extended Spectrum β-lactamase (ESBL), a novel resistance induced by Enterobacteriaceae. There is no Oxyimino group in the structure of Flomoxef, so it won’t derive ESBL and it is also effective for the treatment to ESBL infection. No disulfiram-like reaction and less incidence of vitamin K deficiency than that of Latamoxef. Marketed in Japan as FLUMARIN.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
FLUMARIN
Curative
FLUMARIN
Curative
FLUMARIN

Cmax

ValueDoseCo-administeredAnalytePopulation
38.9 mg/L
500 mg single, intravenous
FLOMOXEF plasma
Homo sapiens
76.6 mg/L
1000 mg single, intravenous
FLOMOXEF plasma
Homo sapiens
33.3 μg/mL
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
36 μg/mL
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
17.6 μg/mL
5 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
10 μg/mL
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
53.1 mg × h/L
500 mg single, intravenous
FLOMOXEF plasma
Homo sapiens
111.9 mg × h/L
1000 mg single, intravenous
FLOMOXEF plasma
Homo sapiens
616.5 μg × h/mL
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
611.5 μg × h/mL
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
387 μg × h/mL
5 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
15.2 μg × h/mL
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
15.03 h
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
13.63 h
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
16.77 h
5 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens
0.66 h
10 mg/kg single, intravenous
FLOMOXEF serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
65%
FLOMOXEF serum
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
The usual dose is 1 to 2 g daily in two divided doses. In general, for adults, the medicine is administered by intravenous injection or intravenous drip infusion daily in 2 divided doses. For children, it is administered by intravenous injection or intravenous drip infusion daily in 3 or 4 divided doses. For premature infants and neonates within 3 days after birth, it is administered by intravenous injection or intravenous drip infusion daily in 2 or 3 divided doses. For premature infants and neonates on the 4th day or later after birth, it is administered by intravenous injection or intravenous drip infusion daily in 3 or 4 divided doses. In case of intractable and/or severe infections, for adults, the medicine is administered by intravenous injection or intravenous drip infusion daily in 2 to 4 divided doses, and for premature infants, neonates and children, the medicine is administered by intravenous injection or intravenous drip infusion daily in 3 or 4 divided doses.
Route of Administration: Intravenous
In Vitro Use Guide
The distribution of MIC's of Flomoxef against Escherichia coli and Salmonella spp. ranged from 0.05 to 0.78 ug/ml and from 0.05 to 0.39 ug/ml, respectively.
Substance Class Chemical
Record UNII
445HIB8XNF
Record Status Validated (UNII)
Record Version