(+)-Ketoconazole

Base Information

• Chemical Name: (+)-Ketoconazole
• CAS No.: 142128-59-4
• Molecular Formula: C₂₆H₂₈Cl₂N₄O₄
• Molecular Weight: 531.439
• European Community (EC) Number: 265-667-4
• ICSC Number: 1700
• UN Number: 2811
• DSSTox Substance ID: DTXSID7029879,DTXSID901316748
• Nikkaji Number: J301.871G
• Wikipedia: Ketoconazole
• Wikidata: Q27121163
• NCI Thesaurus Code: C605
• RXCUI: 6135
• Pharos Ligand ID: P3T7AVNKGKBA
• Metabolomics Workbench ID: 56947
• ChEMBL ID: CHEMBL75
• Mol file: 142128-59-4.mol

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

Chemical Property of (+)-Ketoconazole

Chemical Property:

• PSA: 69.06000
• LogP: 4.20870
• Solubility.: ≥25.5 mg/mL in DMSO with gentle warming; insoluble in H2O; insoluble in EtOH
• 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:

>98% ^*data from raw suppliers

(+)-Ketoconazole ^*data from reagent 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: Ketoconazole in Treating Participants With Ongoing EGFR Inhibitor-Induced Rash
• Recent EU Clinical Trials: A phase 2, randomized, vehicle and ketoconazole-controlled, evaluator-blinded, study to explore the efficacy, pharmacodynamics and safety of omiganan 1.75% topical gel BID in patients with mild to moderate facial seborrheic dermatitis.
• 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-methanesulfonylpiperazine

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

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

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

Refernces

• 1、 Li, Yuanyuan,Li, Qiang,Zhu, Nan,Gao, Zhuxian,Ma, Yulong. "Cellulose type chiral stationary phase based on reduced graphene oxide@silica gel for the enantiomer separation of chiral compounds". . p. 996 - 1004. Retrieved 2018/07/29.
• 2、 Camps, Pelayo,Farres, Xavier,Garcia, Luisa,Ginesta, Joan,Pascual, Jaume,et al.. "Stereoselective Syntheses of Both Enantiomers of Ketoconazole from (R)- and (S)-Epichlorohydrin". . p. 1283 - 1294. Retrieved 2007/10/03.