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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18F2N6O7S2
Molecular Weight 496.466
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLOMOXEF

SMILES

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

InChI

InChIKey=UHRBTBZOWWGKMK-DOMZBBRYSA-N
InChI=1S/C15H18F2N6O7S2/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)/t12-,15+/m1/s1

HIDE SMILES / InChI
Molecular Formula C15H18F2N6O7S2
Molecular Weight 496.466
Charge 0
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

Shionogi
37

Approval Year

Unknown
149,124

Targets

Primary TargetPharmacologyConditionPotency
Streptococcus pneumoniae
25
Inhibitor
8,504
Escherichia coli
82
Inhibitor
8,504
Salmonella sp.
2
Inhibitor
8,504
Haemophilus influenzae
10
Inhibitor
8,504
Bacterial penicillin-binding protein
234
Inhibitor
8,504

Conditions

ConditionModalityTargetsHighest PhaseProduct
Respiratory tract infections
85
 Curative
Approved
8,583
FLUMARIN
Urinary tract infections
207
 Curative
Approved
8,583
FLUMARIN
Intra-abdominal infections
50
 Curative
Approved
8,583
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

Patents

CN103524534A
2
CN104327100A
2

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
V9E5U5XF42
Record Status Validated (UNII)
Record Version
NIH
NCATS
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