Cefmenoxime

Absorption

Bioavailability is approximately 100% following intramuscular injection.

Toxicity

Information on cefmenoxime overdosage in humans is not available. However, with other b-lactam antibiotics, adverse effects following overdosage have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.

Originator

Tacef,Takeda,W. Germany,1983

The Uses of Cefmenoxime

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

The Uses of Cefmenoxime

Antibacterial.

Indications

Used to treat female gynecologic and obstetric infections caused by susceptible aerobic (including the gonococcus) and anaerobic bacteria.

Background

Cefmenoxime is a novel broad-spectrum and third-generation cephalosporin antibiotic that is typically used in the treatment of female gynecologic and obstetric infections. It is reported to exhibit high activity against a wide variety of gram-positive and gram-negative bacteria.

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.

Pharmacokinetics

Cefmenoxime is a semisynthetic beta-lactam cephalosporin antibiotic with activity similar to that of cefotaxime. It has broad spectrum activity against Gram positive and Gram negative bacteria.

Metabolism

Not appreciably metabolized.