| Identification | More | [Name]
Cefmenoxime | [CAS]
65085-01-0 | [Synonyms]
(6r-(6alpha,7beta(z)))-7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((1-methyl-1h-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
CEFMENOXIME
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, [6R-[6α,7β(Z)]]-
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-, (6R,7R)-
AB 50912
SCE 1365
(6R-(6alpha,7beta(Z)))-7-(((2-Amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
[6R-[6α，7β(Z)]]-7-[[(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-y1)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oet-2-ene-2-carboxylic acid
(6R,7R)-7-[[(Z)-(2-Aminothiazol-4-yl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R,7R)-7α-[2-(2-Amino-4-thiazolyl)-2-[(Z)-methoxyimino]acetylamino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
7β-[[(Z)-(2-Amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-[[(1-methyl-1H-tetrazole-5-yl)thio]methyl]cepham-3-ene-4-carboxylic acid
CMX | [EINECS(EC#)]
278-299-4 | [Molecular Formula]
C16H17N9O5S3 | [MDL Number]
MFCD00864851 | [Molecular Weight]
511.56 | [MOL File]
65085-01-0.mol |
| Hazard Information | Back Directory | [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. |
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