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PZ0005

Sigma-Aldrich

Voriconazole

≥98% (HPLC), powder, ergosterol synthesis inhibitor

Synonym(s):

2R,3S-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, UK-109496

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About This Item

Empirical Formula (Hill Notation):
C16H14F3N5O
CAS Number:
137234-62-9
Molecular Weight:
349.31
MDL number:
MFCD00905717
UNSPSC Code:
12352200
PubChem Substance ID:
329823674
NACRES:
NA.77

product name

Voriconazole, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

SMILES string

C[C@@H](c1ncncc1F)[C@](O)(Cn2cncn2)c3ccc(F)cc3F

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

InChI key

BCEHBSKCWLPMDN-MGPLVRAMSA-N

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General description

Voriconazole is a triazole and a synthetic derivative of fluconazole.

Application

Voriconazole has been used:
  • as a control and Erg11 inhibitor in YPD medium
  • as a reference drug to test the activity of essential oils against clinical strains of Candida sp.
  • as an antifungal agent to test its interactions with valproic acid (VPA)
  • to compare its in vitro antifungal activity with essential oils and its components against Cryptococcus neoformans azole-susceptible and not-susceptible clinical isolates

Biochem/physiol Actions

Voriconazole is an antifungal used to treat serious fungal infections. Voriconazole inhibits ergosterol synthesis by inhibiting CYP450-dependent 14-α sterol demethylase resulting in a depletion of ergosterol in fungal cell membranes.
Voriconazole is used to treat invasive aspergillosis (IA). It is vigorous against Candida species, including the strains of Candida albicans, which shows resistance to fluconazole.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Chronic 3 - Carc. 2 - Muta. 2 - Repr. 2 - STOT RE 1 - STOT RE 2 Oral - STOT SE 2 Oral

Target Organs

Eyes, Liver,Kidney

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Identification and evaluation of novel acetolactate synthase inhibitors as antifungal agents
Richie D L, et al.
Antimicrobial agents and chemotherapy, 57(5), 2272-2280 (2013)
pH-dependant antifungal activity of valproic acid against the human fungal pathogen Candida albicans
Chaillot J, et al.
Frontiers in Microbiology, 8, 1956-1956 (2017)
Voriconazole: a new triazole antifungal agent
Saravolatz L D, et al.
Clinical Infectious Diseases, 36(5), 630-637 (2003)
Voriconazole and posaconazole therapeutic drug monitoring: a retrospective study
Whitley M Y, et al.
Annals of Clinical Microbiology and Antimicrobials, 16(1), 60-60 (2017)
Liquid and vapour-phase antifungal activities of essential oils against Candida albicans and non-albicans Candida
Mandras N, et al.
BMC Complementary and Alternative Medicine, 16(1), 330-330 (2016)
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