| Identification | More | [Name]
Flomoxef | [CAS]
99665-00-6 | [Synonyms]
5-OXA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID, 7-[[[(DIFLUOROMETHYL)THIO]ACETYL]AMINO]-3-[[[1-(2-HYDROXYETHYL)-1H-TETRAZOL-5-YL]THIO]METHYL]-7-METHOXY-8-OXO-, (6R-CIS)-
FLOMOXEF
FLOMOXEF [5-OXA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID, 7-[[[(DIFLUOROMETHYL)THIO]ACETYL]AMINO]-3-[[[1-(2-HYDROXYETHYL)-1H-TETRAZOL-5-YL]THIO]METHYL]-7-METHOXY-8-OXO-, (6R-CIS)-]
5-Oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-, (6r-cis)-
5-Oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[[(difluoromethyl)thio]acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-, (6R,7R)-
Flumarin
FMOX
(-)-(6R,7R)-7-(2-((Difluoromethyl)thio)acetamido)-3-(((1-(2-hydroxyethyl)-1H-tetrazol-5-yl)thio)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(-)-(6R,7R)-7-(2-((Difluoromethyl)thio)acetamido)-3-(((1-(2-hydroxyethyl)-1H-tetrazol-5-yl)thio)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R-cis)-7-[[[(Difluoromethyl)thio]acetyl]amino]-3_[[[1-(2-hy-droxyethyl)-1H-tetrazol-5-y1]thio]methyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7α-[[(Difluoromethyl)thio]acetylamino]-7-methoxy-8-oxo-3-[[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thio]methyl]-1-aza-5-oxabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
[6R,7R,(-)]-7α-[[2-(Difluoromethylthio)acetyl]amino]-3-[[[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thio]methyl]-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | [Molecular Formula]
C15H18F2N6O7S2 | [MDL Number]
MFCD00865115 | [Molecular Weight]
496.47 | [MOL File]
99665-00-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
82.5-87.5° | [density ]
1.85±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
soluble in DMSO, Methanol | [form ]
Solid | [pka]
3.26±0.40(Predicted) | [color ]
Off-White | [InChIKey]
UHRBTBZOWWGKMK-DOMZBBRYSA-N | [SMILES]
N12[C@@]([H])([C@@](NC(CSC(F)F)=O)(OC)C1=O)OCC(CSC1N(CCO)N=NN=1)=C2C(O)=O | [CAS DataBase Reference]
99665-00-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Flomoxef sodium is a P-lactamase resistant oxacephalosporin. Its spectrum of activity is
similar to that of cefazolin and moxalactam, but with better efficacy against
Staphylococcus aureus and Bacteroides fragilis. Flomoxef is reported effective in the
treatment of post-operative, urinary tract and abdominal cavity infections. | [Chemical Properties]
Crystallized from acetone-dichloromethane, melting point 82.5～87.5℃. | [Originator]
Shionogi (Japan) | [Uses]
Flomoxef is an oxacephem derived beta-lactam antibiotic that is particularly effective against gram-positive bacteria. | [Definition]
ChEBI:Flomoxef is a second-generation oxacephem antibiotic in which the oxazine ring is substituted at C-3 with a hydroxyethyl-substituted tetrazolylthiomethyl group and the azetidinone ring carries 7alpha-methoxy and 7beta-{2-[(difluoromethyl)thiomethyl]acetamido} substituents. It has a role as an antibacterial drug. It is a N-acyl-amino acid, an oxacephem and an organonitrogen heterocyclic antibiotic. | [Brand name]
Flumari | [Antimicrobial activity]
An oxa-cephem which differs from latamoxef in the side
chains carried at the 7-amino and C-3 positions, but which
retains the 7-methoxy group that confers β-lactamase stability.
The methyl group of the methylthiotetrazole side chain of
latamoxef has been modified to hydroxymethyl in an attempt
to avoid the undesirable side effects, while the side chain at
the 7-amino position is F2-CH-S-CH2-.
Activity is similar to that of latamoxef, but activity against
Staph. aureus is improved and it is claimed to be a poor inducer
of penicillin-binding protein 2′, which is associated with resistance
in methicillin-resistant strains.
Intravenous injection of 2 g achieves a peak plasma concentration
of around 50 mg/L, falling to 2.6 mg/L after 6 h.
The plasma half-life is about 50 min. It appears to be well distributed
and penetrates moderately well into lung, mucosal
tissue of the middle ear and bone.
Flomoxef does not seem to be prone to the effects on platelet
function of latamoxef and it has a less marked effect on
vitamin K metabolism. It does not cause a disulfiram-like
reaction with alcohol.
It is available in Japan, where it appears safe and effective
in a wide range of infections. | [storage]
Store at -20°C |
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