65085-01-0

Basic information

• Product Name: Cefmenoxime
• Synonyms: CEFMENOXIME;(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;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-[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
• CAS NO: 65085-01-0
• Molecular Formula: C16H17N9O5S3
• Molecular Weight: 511.56
• EINECS: 278-299-4
• Product Categories: Pharmaceutical intermediate
• Mol File: 65085-01-0.mol
• Article Data: 6

Chemical Properties

• Appearance: White or light yellow crystalline powder, odourless
• Density: 1.96 g/cm³
• PKA: 2.61±0.50(Predicted)
• CAS DataBase Reference: Cefmenoxime(CAS DataBase Reference)
• NIST Chemistry Reference: Cefmenoxime(65085-01-0)
• EPA Substance Registry System: Cefmenoxime(65085-01-0)

Safety Data

• Hazardous Substances Data: 65085-01-0(Hazardous Substances Data)

Usage

Originator

Tacef,Takeda,W. Germany,1983

Uses

Different sources of media describe the Uses of 65085-01-0 differently. You can refer to the following data:
1. Cefmenoxime (cas# 65085-01-0) is a compound useful in organic synthesis.
2. Antibacterial.

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.

InChI:InChI=1/C16H17N9O5S3/c1-24-16(20-22-23-24)32-5-6-4-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-3-18-15(17)33-7/h3,9,13H,4-5H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29)/b21-8+/t9-,13-/m1/s1

Upstream product

• 24209-38-9 (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid 
• 207725-19-7 (2-Amino-thiazol-4-yl)-[(Z)-methoxyimino]-acetic acid 4,6-dimethoxy-[1,3,5]triazin-2-yl ester 
• 65872-41-5 cefotaxime 
• 24209-38-9 3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 179258-53-8 4-(diethylphosphoryl)-2-(2-amino-4-thiazolyl)-2-syn-(2-methoxyimino)acetate 
• 65243-35-8 (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 

Relevant articles and documents

NOVEL INTERMEDIATES FOR SYNTHESIS OF CEPHALOSPORINS AND PROCESS FOR PREPARATION OF SUCH INTERMEDIATES

A novel 4-halo-2-oxyimino-3-oxo butyric acid-N, N-dimethyl formiminium chloride chlorosulfate of formula (I) useful in the preparation of cephalosporin antibiotics, wherein X is chlorine or bromine; R is hydrogen, C1-4 alkyl group, an easily removable hydroxyl protective group, -CH2COOR5, or -C(CH3)2COOR5, wherein R5 is hydrogen or an easily hydrolysable ester group. The compound of formula (I) is prepared by reacting 4-halo-2-oxyimino-3-oxobutyric acid of formula (IV1), wherein X, R and R5 are as defined above, with N, N-dimethylformiminium chloride chlorosulphate of formula (VII), in an organic solvent at a temperature ranging from -30 °C to -15 °C. The cephalosporins that may be prepared from the intermediate include cefdinir, cefditoren pivoxil, cefepime, cefetamet pivoxil, cefixime, cefmenoxime, cefodizime, cefoselis, cefotaxime, cefpirome, cefpodoxime proxetil, cefquinome, ceftazidime, cefteram pivoxil, ceftiofur, ceftizoxime, ceftriaxone and cefuzonam.

Diethyl chlorophosphate: An effective and convenient coupling reagent of cephalosporin derivatives

A coupling reagent, diethyl chlorophosphate (DECP) 2, was reacted with 2-(2-amino-4-thiazolyl)-2-syn-alkoxyiminoacetic acid 1 to give an active ester intermediate 3.

Studies on orally active cephalosporin esters. II. Chemical stability of pivaloyloxymethyl esters in phosphate buffer solution

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