Cefmenoxime

ChEBI: A third-generation cephalosporin antibiotic, bearing a 2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino group at the 7beta-position and a [(1-methyl-1H-tetrazol-5-yl)sulfanyl]methyl group at the 3-position.

A cephalosporin antibiotic that is administered intravenously or intramuscularly. It is active against most common gram-positive and gram-negative microorganisms, is a potent inhibitor of Enterobacteriaceae, and is highly resistant to hydrolysis by beta-lactamases. The drug has a high rate of efficacy in many types of infection and to date no severe side effects have been noted.

Method 1: Use cefotaxime as raw material. The trifluoroacetate salt of cefotaxime was dissolved in 272rng 1-methyl-5-mercapto. In a solution of 1H-tetrazole, 555mg sodium bicarbonate, 68mg triethylphenylammonium bromide and 10ml water, the reaction was carried out at 60°C for 6h in a nitrogen atmosphere. Cool, and pass through a column equipped with Amberlite XAD-2. Start with water and then 2.5% ethanol to obtain the sodium salt of Cefmenoxime, with a melting point of 174-175°C (decomposition). Method 2: Dissolve compound (I) and triethylamine in 50% tetrahydrofuran aqueous solution, add dropwise the compound (II) tetrahydrofuran solution (see cefotaxime sodium for the preparation method) under ice cooling, and then stir at room temperature after the addition 1h. Water and ethyl acetate were added, and the aqueous layer was adjusted to Ph=2.0 with phosphoric acid. After shaking, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers are combined, and after conventional treatment, compound (III) is obtained. The compound (III) was dissolved in dimethylacetamide (hydrazine chamber), thiourea was added, and the mixture was stirred at room temperature for 15 hours. Pour into ice water and adjust to Ph=3.5 with sodium bicarbonate. The precipitated solid was collected by filtration, dissolved in 5% sodium bicarbonate aqueous solution, chromatographed with Amberlite XAD-2, eluted with water and then 2% ethanol aqueous solution, and lyophilized to obtain cefmenoxime sodium.

Cephalosporin broad-spectrum antibiotics have strong activity against Gram-negative bacteria and are very stable to β-lactamase, and must be administered by injection. Clinically used for respiratory tract infections, urinary tract infections, female reproductive organ infections, biliary tract infections, peritonitis, surgery, gynecological and facial diseases infections caused by sensitive bacteria.

Molecular Weight:511.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:14
Rotatable Bond Count:8
Exact Mass:511.05147820
Monoisotopic Mass:511.05147820
Topological Polar Surface Area:270
Heavy Atom Count:33
Complexity:890
Undefined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes