Disodium (7R)-7-[[4-(carbamoyl-carboxylato-methylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: Disodium (7R)-7-[[4-(carbamoyl-carboxylato-methylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 74356-00-6
• Molecular Formula: C₁₇H₁₅N₇O₈S₄*2Na
• Molecular Weight: 619.592
• Hs Code.: 29419000
• Mol file: 74356-00-6.mol

Synonyms:Apatef;Cefotan;Cefotetan disodium;Cefotetan sodium;Ceftenon;Cepan Darvilen;YM 09330;Yamatetan;(6R,7S)-4-((2-Carboxy-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl)carbamoyl)-1,3-dithietane-D2,a-malonamic Acid Disodium Salt;(6R,7S)-7-(4-(Carbamoylcarboxymethylene)-1,3-dithietane-2-carboxamido)-7-methoxy-3-(((1-methyl-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Disodium Salt;

Chemical Property of Disodium (7R)-7-[[4-(carbamoyl-carboxylato-methylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

• Boiling Point: 798℃
• PSA: 331.27000
• LogP: 0.27540
• Storage Temp.: 2-8°C
• Solubility.: Freely soluble in aqueous solution

Purity/Quality:

98%min ^*data from raw suppliers

Cefotetan disodium ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Cefotetan disodium is a β-lactamase resistant, second generation cephalosporin with a serum half-life of about three hours, permitting twice-daily dosing.
• Uses: Cefotetan Disodium is a related compound of Cefotetan (C242970), an antibiotic related to Cephalosporin that is used to treat bacterial infections. Antibacterial.
• Clinical Use: Cefotetan (Cefotan) is a third-generation cephalosporin thatis structurally similar to cefoxitin. Like cefoxitin, cefotetanis resistant to destruction by β-lactamases. It is also a competitiveinhibitor of many β-lactamases and causes transient inactivation of some of these enzymes. Cefotetan is reportedto synergize with β-lactamase–sensitive β-lactams but, unlikecefoxitin, does not appear to cause antagonism.The antibacterial spectrum of cefotetan closely resemblesthat of cefoxitin. It is, however, generally more activeagainst S. aureus, and members of the Enterobacteriaceaefamily sensitive to both agents. It also exhibits excellentpotency against H. influenzae and N. gonorrhoeae, includingβ-lactamase–producing strains. Cefotetan is slightly lessactive than cefoxitin against B. fragilis and other anaerobes.Enterobacter spp. are generally resistant to cefotetan, andthe drug is without effect against Pseudomonas spp.Cefotetan has a relatively long half-life of about 3.5hours. It is administered on a twice-daily dosing schedule. Itis excreted largely unchanged in the urine. Aqueoussolutions for parenteral administration maintain potency for24 hours at 25°C. Refrigerated solutions are stable for 4 days.Cefotetan contains the MTT group that has been associatedwith hypoprothrombinemia and alcohol intolerance.Another cephalosporin that lacks these properties should beselected for patients at risk for severe bleeding or alcoholism.

Technology Process of Disodium (7R)-7-[[4-(carbamoyl-carboxylato-methylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 3 articles about Disodium (7R)-7-[[4-(carbamoyl-carboxylato-methylidene)-1,3-dithietane-2-carbonyl]amino]-7-methoxy-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.2%

C30H27N7O8S4 → cefotetan disodium (74356-00-6,94199-40-3)

Guidance literature:

C₃₀H₂₇N₇O₈S₄; With methoxybenzene; trifluoroacetic acid; In dichloromethane; di-isopropyl ether; at 0 - 35 ℃;

With sodium hydrogencarbonate; In water; at 10 ℃; pH=6.9; Reagent/catalyst; Solvent; pH-value;

Reference yield: 93.1%

Na(1+)*C30H26N7O8S4(1-) → cefotetan disodium (74356-00-6,94199-40-3)

Guidance literature:

With aluminum (III) chloride; methoxybenzene; In dichloromethane; at 0 ℃;

Reference yield:

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ3-cephem-4-carboxylate (56610-72-1) → cefotetan disodium (74356-00-6,94199-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1,1'-carbonyldiimidazole / ethyl acetate / 10 h / 40 °C

2: hydrogenchloride / tetrahydrofuran; water / 0.5 h / Reflux

3: methoxybenzene; aluminum (III) chloride / dichloromethane / 0 °C

With hydrogenchloride; aluminum (III) chloride; methoxybenzene; 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

upstream raw materials:

diphenylmethyl (6R,7S)-7-amino-7-methoxy-3-<<(1-methyl-1H-tetrazol-5-yl)thio>methyl>-Δ³-cephem-4-carboxylate

Refernces

• 1、 -. "Preparation method of anti-infection cephalosporin drug". . . Retrieved 2021/05/05.