(+/-)-Voriconazole

HCID 71616

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Basic information

CAS: 137234-62-9
Standard SMILES: C[C@@H](c1ncncc1F)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
InChIKey: BCEHBSKCWLPMDN-MGPLVRAMSA-N
Molecular formula: C16H14F3N5O
Average molar mass: 349.316 g/mol
Monoisotopic mass: 349.11504473

Names & identifiers

Preferred name: (+/-)-Voriconazole
IUPAC: (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
English name: Voriconazole-d3
Molecular formula: C16H14F3N5O
Molecular weight: 349.31

Names & synonyms

3R)-2-(2VORICONAZOLE-D3(±)-VoriconazoleVoriconazole PI-6(2R,3R)-VoriconazoleFluconazole Intermediate 2Voriconazole Intermediate IIIntermediate 2 of voriconazole4-triazol-1-yl)-2-butanol (RaceMic Voriconazole)4-Difluorophenyl)-3-(5-fluoro-4-pyriMidinyl)-1-(1H-1

Database identifiers

CAS: 137234-62-9、188416-29-7
PubChem CID: 71616
DTXSID: DTXSID201019420
ChEMBL: CHEMBL638
ChEBI: CHEBI:10023
UNII: JFU09I87TR、USG4B1CD29
EC Number: 629-701-5、941-833-8
Nikkaji: J709.476K

Properties

Physicochemical properties

Boiling point: 508.6 · 508.6±60.0 °C(Predicted)
Density: 1.42 · 1.42±0.1 g/cm3(Predicted)
storage temp.: 2 · Storage temp. 2-8°C
pka: 11.54 · 11.54±0.29(Predicted)
form: Solid
color: White to off-white
InChI: InChI=1/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/s3
InChIKey: BCEHBSKCWLPMDN-NLBNCHMPNA-N
SMILES: C[C@@H]([C@@](CN1C=NC=N1)(C1C(F)=CC(F)=CC=1)O)C1C(F)=CN=CN=1 |&1:1,2,r|
FDA UNII: 4 B1CD29 · USG4B1CD29
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Safety & regulation

Safety data

Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Chemistry & industry

Applications · 2 items

DescriptionVoriconazole-d3 is an Ergosterol biosynthesis inhibitor and a labeled form of Voriconazole. This mono triazole 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 for the biosynthesis of Ergosterol. Furthermore, Voriconazole-d3 inhibits fungal growth, cell wall thinning, and cell membrane degradation.

UsesVoriconazole is a triazole antifungal agent used primarily in the treatment or prevention of aspergillosis and candidal infections. However, its therapy may cause transient, asymptomatic serum aminotransferase elevations, and it is also a well-known cause of acute drug-induced liver injury.