VOR

Voriconazole

Created: 2010-04-01
Last modified:  2021-03-13

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Chemical Details

Formal Charge0
Atom Count39
Chiral Atom Count2
Bond Count41
Aromatic Bond Count17
2D diagram of VOR
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Chemical Component Summary

NameVoriconazole
Synonyms(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
Systematic Name (OpenEye OEToolkits)(2R,3S)-2-[2,4-bis(fluoranyl)phenyl]-3-(5-fluoranylpyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol
FormulaC16 H14 F3 N5 O
Molecular Weight349.31
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01Fc1cncnc1C(C(O)(c2ccc(F)cc2F)Cn3ncnc3)C
SMILESCACTVS3.385C[CH](c1ncncc1F)[C](O)(Cn2cncn2)c3ccc(F)cc3F
SMILESOpenEye OEToolkits1.7.6CC(c1c(cncn1)F)C(Cn2cncn2)(c3ccc(cc3F)F)O
Canonical SMILESCACTVS3.385 C[C@@H](c1ncncc1F)[C@](O)(Cn2cncn2)c3ccc(F)cc3F
Canonical SMILESOpenEye OEToolkits1.7.6 C[C@@H](c1c(cncn1)F)[C@](Cn2cncn2)(c3ccc(cc3F)F)O
InChIInChI1.03 InChI=1S/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+/m0/s1
InChIKeyInChI1.03 BCEHBSKCWLPMDN-MGPLVRAMSA-N

Drug Info: DrugBank

DrugBank IDDB00582 
NameVoriconazole
Groups approved
DescriptionVoriconazole (Vfend, Pfizer) is a triazole antifungal medication used to treat serious fungal infections.[L15571] It is used to treat invasive fungal infections that are generally seen in patients who are immunocompromised. These include invasive candidiasis, invasive aspergillosis, and emerging fungal infections. The increased affinity of voriconazole for 14-alpha sterol demethylase makes it useful against some [fluconazole]-resistant organisms.[A236050] Voriconazole was approved by the FDA under the trade name Vfend on May 24, 2002.[L34660]
Synonyms
  • Voriconazolum
  • Voriconazol
  • (R-(R*,S*))-alpha-(2,4-difluorophenyl)-5-fluoro-beta-methyl-alpha-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
  • Voriconazole
  • (αR,βS)-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
Brand Names
  • Voriconazole
  • Sandoz Voriconazole
  • PMS-voriconazole
  • Jamp Voriconazole
  • Ach-voriconazole
IndicationFor the treatment of esophageal candidiasis, cadidemia, invasive pulmonary aspergillosis, and serious fungal infections caused by <i>Scedosporium apiospermum</i> and <i>Fusarium</i> spp.[L9821, L15571]
Categories
  • 14-alpha Demethylase Inhibitors
  • Anti-Infective Agents
  • Antifungal Agents
  • Antiinfectives for Systemic Use
  • Antimycotics for Systemic Use
ATC-CodeJ02AC03
CAS number137234-62-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome P450 51MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPL...unknownantagonist,inhibitor
Dimethylaniline monooxygenase [N-oxide-forming] 1MAKRVAIVGAGVSGLASIKCCLEEGLEPTCFERSDDLGGLWRFTEHVEEG...unknownsubstrate
Dimethylaniline monooxygenase [N-oxide-forming] 3MGKKVAIIGAGVSGLASIRSCLEEGLEPTCFEKSNDIGGLWKFSDHAEEG...unknownsubstrate
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate,inhibitor
Cytochrome P450 3A7MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...unknownsubstrate,inhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL638
PubChem 71616
ChEMBL CHEMBL638
ChEBI CHEBI:10023
CCDC/CSD HOVFOP01, FUMKAB, FUMKIJ, CEXMAU, TUPFOZ
COD 2212055