Cefmenoxime

Originator

Tacef,Takeda,W. Germany,1983

Uses

Antibacterial.

Uses

Cefmenoxime (cas# 65085-01-0) is a compound useful in organic synthesis.

Definition

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.

Manufacturing Process

7β-[α-Methoxyimino-α-(2-aminothiazol-4-yl)acetamido]cephalosporanicacid trifluoroacetic acid salt is dissolved in a solution of 272 mg of 1-methyl-5- mercapto-1H-tetrazole, 555 mg of sodium bicarbonate and 68 mg of triethylbenzylammonium bromide in 10 ml of water. The solution is heated at 60°C in nitrogen atmosphere for 6 hours. After cooling, the reaction solution is passed through a column of Amberlite XAD-2 and eluted with water and then with 2.5% ethanol. The procedure yields sodium 7β-[α-methoxyimino-α- (2-aminothiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-ylthiomethyl)-3- cephem-4-carboxylate, MP 174°C to 175°C (decomposition).

brand name

Cefmax (TAP).

Therapeutic Function

Antibacterial

Antimicrobial activity

A semisynthetic cephalosporin supplied as the hydrochloride. Its activity is very similar to that of cefotaxime. A 500 mg intramuscular injection achieves a plasma concentration of 15 mg/L after 40 min. A concentration of 200 mg/L is attained after intravenous administration of 1 g. The plasma half-life is c. 1 h. Around 77% is protein bound. Probenecid increases peak plasma levels and extends the plasma half-life to 1.8 h. Therapeutic concentrations are achieved in CSF. There is a degradation product with a long half-life (around 40 h), but 80–92% of the drug is recovered unchanged from the urine. In patients with renal insufficiency, no significant relation was found between creatinine clearance and peak serum concentrations but there was a linear relationship with plasma half-life and total body clearance. About 10% of the dose appears in the feces, mostly extensively degraded, possibly by the fecal flora.
Toxicity, side effects and clinical use are those common to group 4 cephalosporins.