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
• General Description: **7-[(2-Hydroxy-2-phenylacetyl)amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (cefamandole)** is a cephalosporin antibiotic with poor oral absorption in its free form. To enhance bioavailability, its acetoxymethyl (AOM) ester derivative was developed, which shows improved oral absorption in mice when administered in a 50% propylene glycol solution, achieving at least 60% bioavailability. However, absorption is limited by hydrolysis or precipitation in the intestinal lumen before uptake. **Return:** Cefamandole is a cephalosporin antibiotic with limited oral absorption in its native form, but its acetoxymethyl ester derivative exhibits improved bioavailability when delivered in a partially non-aqueous vehicle, though absorption is hindered by intestinal hydrolysis or precipitation.

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:

(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 acetoxymethyl 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-glycyloxymethyl 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-valyloxymethyl 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-leucyloxymethyl ester

Refernces

Orally active esters of cephalosporin antibiotics. II. Synthesis and biological properties of the acetoxymethyl ester of cefamandole

10.7164/antibiotics.32.1155

The research focuses on the synthesis and biological properties of the acetoxymethyl (AOM) ester of cefamandole (CM), a cephalosporin antibiotic. The purpose of the study was to improve the oral absorption of cefamandole, which is not efficiently absorbed when administered orally in its free form. The researchers synthesized the AOM ester of cefamandole and found that it was well absorbed orally by mice, but only when administered in a partially non-aqueous vehicle, specifically a 50% propylene glycol solution. The conclusions drawn from the study indicate that the AOM ester of cefamandole is rapidly and efficiently absorbed orally, demonstrating at least 60% oral bioavailability, and this absorption is limited by the hydrolysis or precipitation of the ester in the intestinal lumen prior to absorption.

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