Ketoconazole

Base Information

• Chemical Name: Ketoconazole
• CAS No.: 142128-57-2
• Deprecated CAS: 72093-26-6
• Molecular Formula: C₂₆H₂₈Cl₂N₄O₄
• Molecular Weight: 531.439
• European Community (EC) Number: 265-667-4
• ICSC Number: 1700
• UN Number: 2811
• UNII: 2DJ8R0NT7K,R9400W927I
• DSSTox Substance ID: DTXSID60161949
• Nikkaji Number: J301.870I
• Wikipedia: Ketoconazole
• Wikidata: Q27120779
• NCI Thesaurus Code: C605
• RXCUI: 6135
• Pharos Ligand ID: P3T4QU5P8AG2
• Metabolomics Workbench ID: 41940
• ChEMBL ID: CHEMBL295698
• Mol file: 142128-57-2.mol

Synonyms:Ketoconazole;Nizoral;R 41400;R-41400;R41,400;R41400

Chemical Property of Ketoconazole

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 530.1487608
• Heavy Atom Count: 36
• Complexity: 735

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Drug Classes: Antifungal Agents
• Canonical SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
• Isomeric SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@@H]3CO[C@@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
• Recent ClinicalTrials: Open-label Treatment in Cushing's Syndrome
• Recent EU Clinical Trials: An Open-label Extension Study of Levoketoconazole (2S,4R-ketoconazole) in the Treatment of Endogenous Cushing’s Syndrome
• Recent NIPH Clinical Trials: The elucidation of influence and mechanisms of antifungal drugs to skin disorders caused by molecular target drugs
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Long Term Exposure: The substance may have effects on the endocrine system and liver. Animal tests show that this substance possibly causes toxicity to human reproduction or development.

Technology Process of Ketoconazole

There total 14 articles about Ketoconazole 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:

ketokonazole → ketoconazole (65277-42-1) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7)

Guidance literature:

With Beckman P/ACE MDQ Capillary Electrophoresis System equipped fused-silica capillaries (Polymicro Technologies, Phoenix, Arizona) of 50-μm ID cut with sulfobutyl ether β-cyclodextrin as chiral selector; In aq. buffer; at 25 ℃; pH=2.5; Concentration; pH-value; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/chir.22777

Reference yield:

ketoconazole (65277-42-1) → ketoconazole (65277-42-1) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7)

Guidance literature:

With cellulose (3,5-dimethylphenylcarbamate) coated reduced graphene oxide(at)silica gel; In hexane; at 25 ℃; enantioselective reaction; Resolution of racemate;

DOI:10.1002/chir.22976

Reference yield:

1-(4-{4-[2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-ethanone (79156-75-5) → ketoconazole (65277-42-1) + (2R,4R)-Ketoconazole (142128-58-3) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7) + (2S,4S)-Ketoconazole (142128-60-7)

Guidance literature:

With methanol; sodium dodecyl-sulfate; 2,3,6-trimethyl-beta-cyclodextrin; sodium hydroxide; In aq. phosphate buffer; at 25 ℃; pH=2.5; pH-value; Reagent/catalyst; Temperature; Resolution of racemate;

DOI:10.1002/chir.22416

upstream raw materials:

trans-<2-(2,4-Dichlorophenyl)-2-<1H-imidazol-1-yl>methyl-(1,3-dioxolan-4-yl)>methyl methanesulfonate

N-acetyl-N'-(4-hydroxyphenyl)piperazine

1-(4-hydroxy-phenyl)-piperazine dihydrobromide

1-(4-Acetoxyphenyl)-4-acetylpiperazine

Downstream raw materials:

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-difluoromethanesulfonylpiperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-trifluoromethanesulfonylpiperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(oxane-4-sulfonyl)piperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(2-methoxyethanesulfonyl)piperazine

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