99665-00-6

Basic information

• Product Name: Flomoxef
• Synonyms: 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)-;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,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-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
• CAS NO: 99665-00-6
• Molecular Formula: C15H18F2N6O7S2
• Molecular Weight: 496.47
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 99665-00-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 82.5-87.5°
• Boiling Point: 232-233°C(lit.)
• Flash Point: >230°F
• Appearance: /
• Density: 1.856 g/cm³
• Refractive Index: 1.731
• CAS DataBase Reference: Flomoxef(CAS DataBase Reference)
• NIST Chemistry Reference: Flomoxef(99665-00-6)
• EPA Substance Registry System: Flomoxef(99665-00-6)

Safety Data

• Hazardous Substances Data: 99665-00-6(Hazardous Substances Data)

Usage

Description

Flomoxef, also known as Flumari, is a P-lactamase resistant oxacephalosporin antibiotic. It is an oxacephem derived beta-lactam antibiotic that is particularly effective against gram-positive bacteria. 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.

Uses

Used in Pharmaceutical Industry:
Flomoxef is used as an antibiotic for the treatment of various infections caused by gram-positive bacteria. Its effectiveness against Staphylococcus aureus and Bacteroides fragilis makes it a valuable option for treating post-operative, urinary tract, and abdominal cavity infections.

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.

InChI:InChI=1/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

Upstream product

• 949587-46-6 ((6R,7R)-7-(2-((difluoromethyl)thio)acetamido)-3-(((1-(2-hydroxyethyl)-1H-tetrazol-5-yl)sulfide)methyl)-7-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-en-2-(diphenylmethyl)carboxylate) 
• 949587-46-6 benzhydryl 7β-[2-(difluoromethylthio)acetamido]-7α-methoxy-3-[1-(2-hydroxyethyl)-1H-tetrazol-5-yl]thiomethyl-1-dethia-1-oxa-3-cephem-4-carboxylate 
• 68314-33-0 diphenylmethyl 7β-(phenylacetamido)-7α-methoxy-3-(chloromethyl)-1-oxadethia-3-cephem-4-carboxylate 
• 83494-32-0 difluoromethylsulfanyl-acetic acid 
• 68314-38-5 (6R,7R)-benzhydryl 7-(4-methylbenzamide)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 949587-46-6 (6R,7R)-7-(2-((difluoromethyl)thio)acetamido)-3-(((1-(2-hydroxyethyl)-1H-tetrazol-5-yl)thio)methyl)-7-methoxyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-formic acid diphenylmethyl ester 
• 103057-61-0 (6R,7R)-7-(amino)-3-(((1-(2-hydroxyethyl)-1H-tetrazol-5-yl)thio)methyl)-7-methoxyl-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-formic acid diphenylmethyl ester 
• 91177-27-4 7-(N-4-methylbenzamide)-3-(chloromethyl)-8-oxo-5-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester 

Relevant articles and documents

Process for preparing cefoxef sodium (by machine translation)

The invention discloses a preparation process, namely, cefoxef sodium. The cefuroxime acid ((6R, 7R) -7 - (( (trifluoromethyl) thio) (2 - (( -3 - (difluorophenyl) thio) methyl) 1 - methoxy 2 - oxo -5 - ox -7 -azabicyclo [-8 -] -2 - octan -2 -5 - formic acid) -1 - is used as a raw 4.2.0 material and reacted with inorganic sodium salt in an aqueous organic solvent A to obtain an aqueous sodium flurosporin-containing aqueous solution after dehydration treatment with anhydrous sodium sulfate, for example. An organic solvent B is added to crystallize to obtain a fluxef sodium solid, and the preparation process avoids the problem, in the traditional solvent crystallization process, organic acid residue, and simultaneously avoids the problem, in the freeze-drying process, the sodium bicarbonate consumption is not clear and the inorganic salt remains. (by machine translation)

A β - lactam compound carboxy and hydroxy protecting group removing method (by machine translation)

The invention discloses a β - lactam compound carboxyl and hydroxyl protecting group removal method, the method is that the carboxyl and/or hydroxyl protected β - lactam compounds in the trichloro acetic acid and carbon is ion absorbent for removing protecting group and gets the role of β - lactam compound deprotected product. The method adopts the trichloro acetic acid instead of trifluoro acetic acid, trichloro acetic acid and phenol or cresol and, anisole together, can greatly reduce the consumption of the trichloroacetic acid; in addition, trichloro acetic acid in the cephalosporin into sodium salt in the follow-up process meets the volunteer fire brigade into chloroform and carbon dioxide, is easy to remove, does not exist the problem of residual of the trichloroacetic acid, the reaction yield is high, relatively few impurities; trichloro acetic acid is inexpensive and environmentally friendly, reduce the cost beneficial to industrial production. (by machine translation)

Method for synthesizing flomoxef acid

The invention relates to a method for synthesizing flomoxef acid. The method comprises the following steps: 1) in an organic solvent, generating a compound (II) from a compound (I) and di-tert butyl dicarbonate under catalysis of organic alkali; 2) in the organic solvent, generating a compound (III) under the action of N,N'-diethylethylenediamine; 3) generating a compound (IV) through methoxylation reaction; 4) connecting the compound (IV) with a tetrazole side chain so as to obtain a compound (V); 5) under the action of trifluoroacetic acid, removing amino and carboxyl protection groups so as to obtain a compound (VI); and 6) enabling the compound (VI) to react with an intermediate of difluromethyl mercaptoacetic acid active ester, thereby obtaining flomoxef acid (VII). The reaction route is as shown in the specification. The method provided by the invention is high in yield, gentle in reaction condition and simple and convenient in after-treatment, and the tetrazole side chain does not need to be protected, so that problems of use and metal residues of dangerous reagents such as phosphorus pentachloride and high boiling point reagents such as anisole in deprotection reaction can be avoided.