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Merck

PZ0005

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
UNSPSC Code:
12352200
PubChem Substance ID:
329823674
NACRES:
NA.77
MDL number:
MFCD00905717

Product Name

Voriconazole, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

Quality Level

100

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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 an antifungal, which inhibits ergosterol synthesis.
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.

General description

Voriconazole is a triazole and a synthetic derivative of fluconazole.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

signalword

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000216962
0000216962
0000210740
0000210740
030M4705V

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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)
Narcisa Mandras et al.
Molecules (Basel, Switzerland), 26(16) (2021-08-28)
The epidemiology of yeast infections and resistance to available antifungal drugs are rapidly increasing, and non-albicans Candida species and rare yeast species are increasingly emerging as major opportunistic pathogens. In order to identify new strategies to counter the threat of
Use of Pinus sylvestris L.(Pinaceae), Origanum vulgare L.(Lamiaceae), and Thymus vulgaris L.(Lamiaceae) essential oils and their main components to enhance itraconazole activity against azole susceptible/not-susceptible Cryptococcus neoformans strains
Scalas D, et al.
BMC Complementary and Alternative Medicine, 18(1), 143-143 (2018)
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