Cefditoren

Base Information

• Chemical Name: Cefditoren
• CAS No.: 104145-95-1
• Molecular Formula: C19H18N6O5S3
• Molecular Weight: 506.587
• UNII: 81QS09V3YW
• DSSTox Substance ID: DTXSID501328012
• Wikipedia: Cefditoren
• NCI Thesaurus Code: C72625
• Metabolomics Workbench ID: 43303
• ChEMBL ID: CHEMBL1743
• Mol file: 104145-95-1.mol

Synonyms:cefditoren;cefditoren, sodium salt, (6R-(3(Z),6alpha,7beta(Z)))-isomer;ME 1206;ME-1206

Chemical Property of Cefditoren

Chemical Property:

• Refractive Index: 1.825
• PSA: 246.10000
• Density: 1.76 g/cm³
• LogP: 2.00100
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 7
• Exact Mass: 506.05008122
• Heavy Atom Count: 33
• Complexity: 928

Purity/Quality:

99% ^*data from raw suppliers

Cefditoren-13c,D3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(SC=N1)C=CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)O
• Isomeric SMILES: CC1=C(SC=N1)/C=C\C2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
• Recent EU Clinical Trials: Multicentre, prospective, comparative, randomized, double-blind, double-dummy study to assess the efficacy and safety of cefditoren pivoxil versus ciprofloxacin in acute uncomplicated cystitis.
• Recent NIPH Clinical Trials: None

Technology Process of Cefditoren

There total 11 articles about Cefditoren 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: 97.4%

C13H12N3O3S2(1-)*Na(1+) (1207515-78-3) + ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate (64485-88-7) → cefditoren (104145-95-1)

Guidance literature:

C₁₃H₁₂N₃O₃S₂^(1-)*Na⁽¹⁺⁾; With N-2-hydroxyethylpiperazine-N'-2-ethanesulfonic acid; at 30 - 35 ℃; for 0.5h; pH=7; Enzymatic reaction;

ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate; With hydrogenchloride; sodium hydroxide; In water; at 30 - 35 ℃; for 2h; pH=6.5 - 7.5; Reagent/catalyst; Temperature;

Reference yield: 90.0%

2-mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-2-(2-aminothiazol-4-yl)-2-methoxyimino acetate + (6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (155723-02-7) → cefditoren (104145-95-1)

Guidance literature:

With triethylamine; for 4 - 5h; pH=7.5 - 8.5;

Reference yield: 85.0%

C13H13N3O2S2 + (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) → cefditoren (104145-95-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 5 ℃; for 4h;

upstream raw materials:

(6R,7R)-7-amino-3-[(1Z)-2-(4-methyl-5-thiazolyl)vinyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate

C₁₃H₁₂N₃O₃S₂^(1-)*Na⁽¹⁺⁾

ethyl 2-(2-aminothiazol-4-yl)-2-(anti)-methoxyiminoacetate

Downstream raw materials:

cefditoren pivoxil

7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(Z)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt

7-<(Z)-2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido>-3(E)-(4-methylthiazol-5-yl)vinyl-3-cephem-4-carboxylic acid sodium salt

Refernces

• 1、 -. "Preparation method of cefditoren pivoxil". Paragraph 0007; 0009. . Retrieved 2017/02/24.
• 2、 -. "DEPLETION OF E-ISOMERS IN PREPARATION OF Z-ENRICHED 3-(2-SUBSTITUTED VINYL) CEPHALOSPORINS". Page/Page column 16. . Retrieved 2008/06/13.