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Ravuconazole

Product NameRavuconazole
CAS182760-06-1
MFC22H17F2N5OS
MW437.47
EINECS
MOL File182760-06-1.mol

Chemical Properties

Melting point	64-66°C
alpha	D24 -29.1° (c = 1.03 in methanol)
Boiling point	674.9±65.0 °C(Predicted)
Density	1.38±0.1 g/cm3(Predicted)
storage temp.	-20°C Freezer
solubility	DMF: 25 mg/ml; DMF:PBS (pH 7.2) (1:4): 0.25 mg/ml; DMSO: 20 mg/ml; Ethanol: 5 mg/ml
form	A crystalline solid
pka	11.62±0.29(Predicted)
color	Off-white to yellow
optical activity	[α]/D -27 to -33°, c =1 in methanol
InChI	InChI=1S/C22H17F2N5OS/c1-14(21-28-20(10-31-21)16-4-2-15(9-25)3-5-16)22(30,11-29-13-26-12-27-29)18-7-6-17(23)8-19(18)24/h2-8,10,12-14,30H,11H2,1H3/t14-,22+/m0/s1
InChIKey	OPAHEYNNJWPQPX-RCDICMHDSA-N
SMILES	C(#N)C1=CC=C(C2=CSC([C@H](C)[C@](C3=CC=C(F)C=C3F)(O)CN3C=NC=N3)=N2)C=C1

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Usage And Synthesis

Description

Ravuconazole is an orally available triazole fungicide that potently inhibits the growth of a wide range of fungi (MICs range from 25 to 780 ng/ml). Like other azoles, ravuconazole inhibits cytochrome P450 (CYP) isoforms that are involved in ergosterol biosynthesis, interfering with the generation of the fungal and protozoan cell membranes. Ravuconazole specifically inhibits sterol 14α-demethylase (CYP51). As this enzyme is also important in the development of trypanosomes, ravuconazole is effective against T. cruzi infections in animal models of Chagas disease.

Chemical Properties

Off-White Solid

Uses

Ergosterol biosynthesis inhibitor. Antifungal.

Definition

ChEBI: Ravuconazole is a member of the class of triazoles that is 1-butyl-1H-1,2,4-triazole in which the butyl group is substituted at positions 2, 2, and 3 by hydroxy, 2,4-difluorophenyl, and 4-(p-cyanophenyl)-1,3-thiazol-2-yl groups, respectively (the R,R stereoisomer). It exhibits antifungal activity by inhibition of 14alpha demethylase, an enzyme involved in sterol synthesis, resulting in lysis of the fungal cell wall and fungal cell death. (NCIO4) It has a role as an ergosterol biosynthesis inhibitor, an antifungal drug, an EC 1.14.14.154 (sterol 14alpha-demethylase) inhibitor and an antileishmanial agent. It is a member of triazoles, a member of fluorobenzenes, a tertiary alcohol, a member of 1,3-thiazoles and a nitrile.

in vivo

The maximum concentration of ravuconazole in plasma and the area under the concentration-time curve for ravuconazoleshow good linearity over a range of doses from 2 to 40 mg/kg of body weight. Ravuconazole at a dose of 2.5 mg/kg delays mortality significantly compared with the control treatment.Ravuconazole also shows a substantial therapeutic effect against systemic cryptococcosis^[1]. Ravuconazole reduces the numbers of CFU in the lungs significantly compared with the numbers of CFU in the lungs of the controls. In an experimental model of oral candidiasis in rats, ravuconazole reduces the numbers of CFU in oral swabs significantly compared with the numbers of CFU in oral swabs from the controls and is more effective than itraconazole and as effective as fluconazole.^[3].

References

[1] K HATA. In vitro and in vivo antifungal activities of ER-30346, a novel oral triazole with a broad antifungal spectrum.[J]. Antimicrobial Agents and Chemotherapy, 1996, 40 10: 2237-2242. DOI: 10.1128/aac.40.10.2237
[2] K HATA. Efficacy of ER-30346, a novel oral triazole antifungal agent, in experimental models of aspergillosis, candidiasis, and cryptococcosis.[J]. Antimicrobial Agents and Chemotherapy, 1996, 40 10: 2243-2247. DOI: 10.1128/aac.40.10.2243
[3] A J CARRILLO-MUOZ. Antifungal agents: mode of action in yeast cells.[J]. Revista Espanola De Quimioterapia, 2006, 19 2: 130-139.
[4] JULIO A URBINA . In vitro and in vivo activities of ravuconazole on Trypanosoma cruzi, the causative agent of Chagas disease[J]. International Journal of Antimicrobial Agents, 2003, 21 1: Pages 27-38. DOI: 10.1016/s0924-8579(02)00273-x
[5] LEPESHEVA G I. Design or screening of drugs for the treatment of Chagas disease: what shows the most promise[J]. Expert Opinion on Drug Discovery, 2013, 8 12: 1479-1489. DOI: 10.1517/17460441.2013.845554

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