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Voriconazole

VETRANAL®, analytical standard

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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
Empirical Formula (Hill Notation):
C16H14F3N5O
CAS Number:
137234-62-9
Molecular Weight:
349.31
MDL number:
MFCD00905717
UNSPSC Code:
41116107
PubChem Substance ID:
329754241
NACRES:
NA.24

grade

analytical standard

Quality Level

100

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

application(s)

forensics and toxicology
pharmaceutical (small molecule)

format

neat

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 second-generation triazole, and is derived from fluconazole. It has a broad and enhanced antifungal spectrum as compared to other older triazoles. It is mostly well tolerated and is available in both oral and intravenous formulations.

Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Biochem/physiol Actions

It has been used as one of the constituent of YPD (1% yeast extract, 2% peptone, 2% glucose) liquid media.
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 used to treat serious fungal infections. Voriconazole inhibits ergosterol synthesis by inhibiting CYP450-dependent 14-a sterol demethylase resulting in a depletion of ergosterol in fungal cell membranes.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

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

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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Convergent evolution of calcineurin pathway roles in thermotolerance and virulence in Candida glabrata.
Chen, Ying-Lien, et al.
G3 (Bethesda, Md.), 2 (6), 675- 691 (2012)
Voriconazole: a new triazole antifungal agent.
Saravolatz, Louis D., Leonard B. Johnson, and Carol A. Kauffman.
Clinical Infectious Diseases, 36 (5), 630-637 (2003)
Voriconazole versus amphotericin B for primary therapy of invasive aspergillosis.
Herbrecht, Raoul, et al.
The New England Journal of Medicine, 347 (6), 408-415 (2002)
Kim Vanstraelen et al.
Antimicrobial agents and chemotherapy, 58(11), 6782-6789 (2014-09-04)
Setting the adequate dose for voriconazole is challenging due to its variable pharmacokinetics. We investigated the impact of hypoalbuminemia (<35 g/liter) on voriconazole pharmacokinetics in adult intensive care unit (ICU) patients treated with voriconazole (20 samples in 13 patients) as
Chang Hyun Park et al.
Cornea, 33(9), 928-934 (2014-07-12)
The aim of this study was to evaluate the toxicity of intrastromally injected voriconazole on corneal endothelial cells in rabbits. In total, 32 eyes of 16 rabbits (8 eyes for each group) were divided into 4 groups according to the
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