Ravuconazole

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

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