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
• Description: Cefoxitin contains the same C-7 side chain as cephalothin and the same C-3 side chain as cefuroxime. The most novel chemical feature of cefoxitin is the possession of an α-oriented methoxyl group in place of the normal H-atom at C-7. This increased steric bulk conveys very significant stability against β-lactamases. The inspiration for these functional groups was provided by the discovery of the naturally occurring antibiotic cephamycin C derived from fermentation of Streptomyces lactamdurans. Cephamycin C itself has not seen clinical use but, rather, has provided the structural clue that led to useful agents such as cefoxitin. Agents that contain this 7α methoxy group are commonly referred to as cephamycins. Ingenious chemical transformations now enable synthetic introduction of such a methoxy group into cephalosporins lacking this feature.
• Uses: Cefoxitin?is a semisynthetic, broad-spectrum second-generation cephalosporin with antibacterial activity. The activity of cefoxitin results in the weakening of the bacterial cell wall and causes cell lysis. Cefoxitin acts by interfering with cell wall synthesis. Its activity spectrum includes a broad range of gram-negative and gram-positive bacteria including anaerobes. Antibacterial.
• Therapeutic Function: Antibiotic
• Clinical Use: As for other group 3 cephalosporins, with particular emphasis on mixed infections including anaerobes, notably abdominal and pelvic sepsis. In considering its use, its low activity against aerobic Gram-positive cocci should be noted.

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:

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

(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

Refernces

• 1、 -. "Synthesis method of cefoxitin sodium". Paragraph 0064; 0071; 0073; 0078; 0085; 0086; 0093; 0094. . Retrieved 2019/05/08.
• 2、 -. "A head cefoxitin acid synthesis method". . . Retrieved 2017/07/06.