Cefamandole

Base Information

• Chemical Name: Cefamandole
• CAS No.: 34444-01-4
• Molecular Formula: C₁₈H₁₈N₆O₅S₂
• Molecular Weight: 462.51
• European Community (EC) Number: 252-030-0
• UNII: 5CKP8C2LLI
• DSSTox Substance ID: DTXSID7022750
• Nikkaji Number: J17.432G
• Wikipedia: Cefamandole
• Wikidata: Q2601530
• NCI Thesaurus Code: C353
• Pharos Ligand ID: K5U5GAKNM2PV
• Metabolomics Workbench ID: 43495
• ChEMBL ID: CHEMBL1146
• Mol file: 34444-01-4.mol

Synonyms:Cefamandole;Cephamandole;Compound 83405

Chemical Property of Cefamandole

Chemical Property:

• Appearance/Colour: White to off-white powder
• Refractive Index: 1.7000 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: pKa 2.6–2.9 (Uncertain)
• Flash Point: °C
• PSA: 201.14000
• Density: 1.75 g/cm³
• LogP: 0.10320
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 462.07801004
• Heavy Atom Count: 31
• Complexity: 777

Purity/Quality:

99% ^*data from raw suppliers

R- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=NN=N1)SCC2=C(N3C(C(C3=O)NC(=O)C(C4=CC=CC=C4)O)SC2)C(=O)O
• Isomeric SMILES: CN1C(=NN=N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](C4=CC=CC=C4)O)SC2)C(=O)O
• Description: The pharmacological action and indications for use of cefamandole is analogous to that of cefuroxime and cefamandole. Synonyms of this drug are mandoxef, kefandol, kefadol, and many others.
• Uses: Intermediate for the oreparation of Phenylephrine Glucuronide. Cefamandole is a second-generation cephalosporin antibiotic with antibacterial activity.
• Therapeutic Function: Antibiotic

Technology Process of Cefamandole

There total 5 articles about Cefamandole 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: 60.0%

7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ3-cephem-4-carboxylic acid (51818-85-0) + 1-methyl-5-mercaptotetrazole (13183-79-4) → cefamandole (65338-32-1,144125-09-7,34444-01-4)

Guidance literature:

In water; at 65 ℃;

DOI:10.1016/S0960-894X(01)00463-2

Reference yield:

(R)-methyl mandelate (20698-91-3) + (6R,7R)-7-amino-3-[(1H-1-methyltetrazol-5-yl)thio]methylceph-3-em-4-carboxylic acid (24209-38-9) → cefamandole (65338-32-1,144125-09-7,34444-01-4)

Guidance literature:

With 3G₃K penicillin G acylase immobilized on glyoxyl agarose; at 4 ℃; pH=6.5; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1002/ejoc.200801204

Reference yield:

cefamandole nafate (42540-40-9) → cefamandole (65338-32-1,144125-09-7,34444-01-4)

Guidance literature:

With sodium carbonate;

DOI:10.1002/jps.2600650811

upstream raw materials:

cefamandole nafate

7-[(1-hydroxy-1-phenyl)-acetamido]-3-acetoxymethyl-Δ³-cephem-4-carboxylic acid

1-methyl-5-mercaptotetrazole

(R)-methyl mandelate

Downstream raw materials:

Cefamandole nafate

cefamandole nafate

N-tert-butoxycarbonyl-L-aspartic acid 4-[(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carbonyloxymethyl] ester 1-methyl ester

(6R)-7t-((R)-2-hydroxy-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid N-tert-butoxycarbonyl-L-isoleucyloxymethyl ester

Refernces

• 1、 -. "PROCESS FOR THE FORMYLATION OF CEFAMANDOLE". Page/Page column 8. . Retrieved 2013/05/09.
• 2、 Terreni, Marco,Tchamkam, Joseph Gapesie,Sarnataro, Umberto,Rocchietti, Silvia,Fernandez-Lafuente, Roberto,Guisan, Jose M.. "Influence of substrate structure on PGA-catalyzed acylations. Evaluation of different approaches for the enzymatic synthesis of cefonicid". . p. 121 - 128. Retrieved 2007/10/03.