Cefoxitin

Base Information

• Chemical Name: Cefoxitin
• CAS No.: 35607-66-0
• Molecular Formula: C16H17N3O7S2
• Molecular Weight: 427.459
• Hs Code.: 30032013
• European Community (EC) Number: 252-641-2
• UNII: 6OEV9DX57Y
• DSSTox Substance ID: DTXSID1022764
• Nikkaji Number: J17.441F
• Wikipedia: Cefoxitin
• Wikidata: Q2353907
• NCI Thesaurus Code: C61665
• RXCUI: 2189
• Metabolomics Workbench ID: 43499
• ChEMBL ID: CHEMBL996
• Mol file: 35607-66-0.mol

Synonyms:Cefoxitin;Cefoxitin Sodium;Méfoxin;Mefoxin;Mefoxitin;MK 306;MK-306;MK306;Sodium, Cefoxitin

Chemical Property of Cefoxitin

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 3.24E-30mmHg at 25°C
• Melting Point: 149 - 150oC
• Refractive Index: 1.692
• Boiling Point: 843.4 °C at 760 mmHg
• PKA: 2.2(at 25℃)
• Flash Point: 463.9 °C
• PSA: 201.80000
• Density: 1.63 g/cm³
• LogP: 1.12770
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: Predicted solubility in water is less than 0.2mg/ml
• XLogP3: 0
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 427.05079224
• Heavy Atom Count: 28
• Complexity: 744

Purity/Quality:

99% ^*data from raw suppliers

Cefoxitin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1(C2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
• Isomeric SMILES: CO[C@@]1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)N)C(=O)O)NC(=O)CC3=CC=CS3
• Recent ClinicalTrials: Does Cefoxitin or Piperacillin-Tazobactam Prevent Postoperative Surgical Site Infections After Pancreatoduodenectomy?
• Recent EU Clinical Trials: Intermittent cefoxitin administration versus loading bolus followed by continuous infusion for the prevention of surgical site infection in colorectal surgery: a multicentre, double-blind, randomized controlled clinical trial
• General Description: Cefoxitin is a semi-synthetic cephamycin antibiotic with a 7α-methoxy group and a 2-thienylacetyl side chain, which enhances its stability against β-lactamases and broadens its spectrum of activity, particularly against Gram-negative bacteria. Its structural modifications, including the methoxy substitution and acylamido group, contribute to its potent antibacterial properties, often outperforming other cephalosporins like cephalothin in efficacy.

Technology Process of Cefoxitin

There total 23 articles about Cefoxitin 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: 96.0%

desacetyl cephalosporin C (1476-46-6) → cefoxitin (35607-66-0)

Guidance literature:

desacetyl cephalosporin C; With N,N'-dibenzylethylenediamine diacetate; In dichloromethane; water; at 25 ℃;

With isocyanate de chlorosulfonyle; In dichloromethane; at -40 ℃; Temperature; Further stages;

Reference yield: 82.8%

isocyanate de chlorosulfonyle (1189-71-5) + 2C15H16N2O6S2*C16H20N2 → cefoxitin (35607-66-0)

Guidance literature:

In acetone; at -35 - -30 ℃;

Reference yield: 65.0%

isocyanate de chlorosulfonyle (1189-71-5) + 3-hydroxymethyl-7α-[(2-thienyl)acetamido]-4-cephalosporanic acid benzathine salt → cefoxitin (35607-66-0)

Guidance literature:

isocyanate de chlorosulfonyle; 3-hydroxymethyl-7α-[(2-thienyl)acetamido]-4-cephalosporanic acid benzathine salt; In acetone; at -50 - -45 ℃; for 2h;

With water; In acetone; at 8 - 10 ℃;

upstream raw materials:

isocyanate de chlorosulfonyle

3-hydroxymethyl-7c-methoxy-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

3-acetoxymethyl-7c-methoxy-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; sodium salt

diphenylmethyl (6R, 7S)-7-(2'-thienyl)acetamido-7-methoxy-3-carbamoyloxymethyl-3-cephem-4-carboxylate

Downstream raw materials:

(6R,7S)-3-Carbamoyloxymethyl-7-methoxy-8-oxo-7-(2-thiophen-2-yl-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

cefoxitin sodium

(2R,6R,7S)-3-((carbamoyloxy)methyl)-7-methoxy-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-3-ene-2-carboxylic acid

Refernces

Synthesis of 7α methoxy 7 [2 (substituted thio)acetamido]cephalosporin derivatives and their antibacterial activities

10.1248/cpb.24.2629

The research focused on the synthesis and antibacterial activities of 7a-methoxy-7-[2-(substituted thio)acetamido]cephalosporin derivatives. The purpose was to develop more active cephalosporin derivatives by nucleophilic displacement of the halogen atom of 7β-(2-halogenoacetamido)-7-methoxy cephalosporanic acid derivatives with various mercapto compounds. The study concluded that the synthesized compounds, particularly those with a five-membered heterocyclic ring in the acylamido group, exhibited potent antibacterial activities, with compound (6) showing activities comparable to the semi-synthetic antibiotic cefoxitin and superior to cephalothin against gram-negative bacteria. Key chemicals used in the process included cephamycin C, tert-butoxycarbonyl azide, diphenyldiazomethane, chloroacetyl chloride, bis(trimethylsilyl)trifluoroacetamide, and various mercapto compounds for the nucleophilic displacement reaction.

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