Voriconazole

Names

[ Name ]:
Voriconazole

[Synonym ]:
4-Pyrimidineethanol, 6-chloro-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-, (αS,βR)-, hydrochloride (1:1)
Vfend
(2R,3S)-2-(2,4-Difluorphenyl)-3-(5-fluorpyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
(R-(R*,S*))-a-(2,4-difluorophenyl)-5-fluoro-b-methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol
(2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol
(2S,3R)-3-(6-Chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride (1:1)
(2S,3R)-3-(6-Chloro-5-fluoro-4-pyrimidinyl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol hydrochloride
4-Pyrimidineethanol, α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-, (αR,βS)-
(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
Voriconazole
(2R,3S)-2-(2,4-difluorophényl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol
EINECS 200-261-5
Vorionazole
MFCD00905717
(aR,bS)-a-(2,4-difluorophenyl)-5-fluoro-b-methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol

Biological Activity

[Description]:

Voriconazole(UK-109496) is a second-generation triazole antifungal used to treat serious fungal infections.IC50 Value: Target: AntifungalVoriconazole displays potent activity against Candida, Cryptococcus and Aspergillus species. Voriconazole inhibits ergosterol synthesis by inhibiting CYP450-dependent 14-α sterol demethylase resulting in a depletion of ergosterol in fungal cell membranes.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[References]

[1]. Mikus G, Scholz IM, Weiss J. Pharmacogenomics of the triazole antifungal agent voriconazole. Pharmacogenomics. 2011 Jun;12(6):861-72. doi: 10.2217/pgs.11.18.

[2]. Scholz I, Oberwittler H, Riedel KD, et al. Pharmacokinetics, metabolism and bioavailability of the triazole antifungal agent voriconazole in relation to CYP2C19 genotype. Br J Clin Pharmacol. 2009 Dec;68(6):906-15. doi: 10.1111/j.1365-2125.2009.03534.x.

[3]. Herbrecht R. Voriconazole: therapeutic review of a new azole antifungal. Expert Rev Anti Infect Ther. 2004 Aug;2(4):485-97.

[4]. Louis D. Saravolatz, Section Editor, Leonard B. Johnson, et al. Voriconazole: A New Triazole Antifungal Agent. Clin Infect Dis. 2003,36 (5): 630-637.

[5]. John R. Perfect, Kieren A. Marr, Thomas J. Walsh, et al. Voriconazole Treatment for Less-Common, Emerging, or Refractory Fungal Infections. Clin Infect Dis. 2003, 36 (9): 1122-1131.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
508.6±60.0 °C at 760 mmHg

[ Melting Point ]:
127-130°C

[ Molecular Formula ]:
C₁₆H₁₄F₃N₅O

[ Molecular Weight ]:
349.31

[ Flash Point ]:
261.4±32.9 °C

[ PSA ]:
76.72000

[ LogP ]:
0.93

[ Vapour Pressure ]:
0.0±1.4 mmHg at 25°C

[ Index of Refraction ]:
1.617

[ Storage condition ]:
Store at +4°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS02, GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H301 + H311 + H331-H370

[ Precautionary Statements ]:
P210-P260-P280-P301 + P310-P311

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R22;R36/38

[ Safety Phrases ]:
S26-S36/37/39

[ RIDADR ]:
UN 2811 6.1/PG 3

[ RTECS ]:
UV9145000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Antifungal susceptibility and virulence attributes of animal-derived isolates of Candida parapsilosis complex.

J. Med. Microbiol. 63(Pt 11) , 1568-72, (2014)

This study aimed to identify strains of the Candida parapsilosis complex isolated from animals, as well as to assess their in vitro antifungal susceptibility profile and in vitro production of virulen...

European Confederation of Medical Mycology (ECMM) epidemiological survey on invasive infections due to Fusarium species in Europe.

Eur. J. Clin. Microbiol. Infect. Dis. 33(9) , 1623-30, (2014)

In order to better understand the epidemiology of fusariosis in Europe, a survey collecting information on the clinical characteristics of the patients infected by Fusarium as well as on the infecting...

Simultaneous determination of seven azole antifungal drugs in serum by ultra-high pressure liquid chromatography and diode array detection.

Acta Clin. Belg. 69(1) , 53-61, (2014)

Azole antifungals are a group of fungistatic agents that can be administered orally or parenterally. The determination of the concentrations of these antifungals (miconazole, fluconazole, ketoconazole...