Voriconazole

Base Information

• Chemical Name: Voriconazole
• CAS No.: 188416-29-7
• Deprecated CAS: 173967-54-9
• Molecular Formula: C16H14F3N5O
• Molecular Weight: 349.31000
• European Community (EC) Number: 629-701-5,941-833-8
• NSC Number: 759888
• UNII: JFU09I87TR,USG4B1CD29
• DSSTox Substance ID: DTXSID5046485,DTXSID201019420
• Nikkaji Number: J709.476K
• Wikipedia: Voriconazole
• Wikidata: Q412236
• NCI Thesaurus Code: C1707
• RXCUI: 121243
• Pharos Ligand ID: RMWVQW96R8LU
• Metabolomics Workbench ID: 42913
• ChEMBL ID: CHEMBL638
• Mol file: 188416-29-7.mol

Synonyms:UK 109,496;UK 109496;UK-109,496;UK-109496;UK109,496;UK109496;Vfend;voriconazole

Chemical Property of Voriconazole

Chemical Property:

• Appearance/Colour: white powder
• Boiling Point: 508.6±60.0 °C(Predicted)
• PKA: 11.54±0.29(Predicted)
• PSA: 76.72000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 2.17690
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 349.11504457
• Heavy Atom Count: 25
• Complexity: 448

Purity/Quality:

99%, ^*data from raw suppliers

(±)-Voriconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antifungal Agents
• Canonical SMILES: CC(C1=NC=NC=C1F)C(CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
• Isomeric SMILES: C[C@@H](C1=NC=NC=C1F)[C@](CN2C=NC=N2)(C3=C(C=C(C=C3)F)F)O
• Recent ClinicalTrials: A Pilot of Pediatric/Adult Study of Gene Expression Profiling and Clinical Characterization of Phototoxicity
• Recent EU Clinical Trials: A Phase 3, Multicenter, Prospective, Randomized, Double-blind Study of Two Treatment Regimens for Candidemia and/or Invasive Candidiasis: Intravenous Echinocandin followed by Oral Ibrexafungerp versus Intravenous Echinocandin followed by Oral Fluconazole (MARIO)
• Recent NIPH Clinical Trials: A phase 3, multi-center, open label study to evaluate safety and efficacy of AK1820 for treatment of adult Japanese patients with deep mycosis.
• Description: Voriconazole-d3 is a labeled form of Voriconazole which is an Ergosterol biosynthesis inhibitor. This monotriazole antifungal agent inhibits the growth of Candida, Cryptococcus, and Aspergillus species. Studies suggest that Voriconazole-d3 can be synthesized by modifying the structure of fluconazole. This antifungal agent functions by inhibiting cytochrome P450 dependent 14-α-sterol demethylase, which is responsible in the biosynthesis of Ergosterol. Furthermore, Voriconazole-d3 inhibits fungal growth, cell wall thinning, and cell membrane degradation.
• Uses: Voriconazole is a triazole antifungal agent used primarily in the treatment or prevention of aspergillosis and candidal infections. Voriconazole therapy is associated with transient, asymptomatic serum aminotransferase elevations and is a known cause of clinically apparent acute drug induced liver injury.

Technology Process of Voriconazole

There total 156 articles about Voriconazole 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: 92.5%

(2R,3S/2S,3R)-6-[4-(3,5-dibromo-1H-1,2,4-triazol-1-yl)-3-(2,4-difluorophenyl)-3-hydroxybutan-2-yl]-5-fluoropyrimidin-4-yl methanesulfonate → 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (182230-43-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

With ammonium formate; palladium on carbon; In toluene; at 80 ℃; for 3h;

Reference yield: 92.0%

2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol (137234-63-0,173967-54-9,188416-29-7) → voriconazole (137234-62-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butane-2-ol; With (1S)-10-camphorsulfonic acid; In methanol; acetone; for 1h; Reflux;

With sodium hydroxide; In dichloromethane; water; pH=11 - 12;

Reference yield: 86.3%

C26H28F3N5O5S → voriconazole (137234-62-9,137234-63-0,173967-54-9,188416-29-7)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethanol; under 760.051 Torr;

upstream raw materials:

2-fluoro-3-oxopentanoic acid ethyl ester

6-Ethyl-5-fluoropyrimidin-4(3H)-one

4-chloro-6-ethyl-5-fluoropyrimidine

1-(4-chloro-5-fluoropyrimidin-6-yl)bromoethane

Downstream raw materials:

C₁₆H₁₄F₃N₅O*C₇H₆O₃

C₁₆H₁₄F₃N₅O*C₇H₇NO₂

C₁₆H₁₄F₃N₅O*C₇H₅NO₄

C₁₆H₁₃F₃N₆O₃

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