Ravuconazole is a triazole antifungal, a 1-butyl-1H-1,2,4- triazole. The compound has a broad-spectrum antifungal activity, and is active against molds and yeast. It has a spectrum similar to voriconazole. It inhibits cytochrome P450 14α-demethylase, thus it disupts fungal cell membranes. Structurally, it is similar to fluconazole and voriconazole. Ravuconazole is sparingly soluble in DMSO and DMF.
| Mechanism of Action | Ravuconazole is an inhibitor of sterol biosynthesis via inhibition of cytochrome P450 14α-demethylase, an enzyme involved in the sterol biosynthesis pathway leading from lanosterol to ergosterol, which results in disruption of fungal cell membranes. The enzyme is also involved in the development of trypanosomes and can disrupt protozoal cell membranes. |
| Spectrum | Ravuconazole has broad-spectrum antifungal activity in vitro. Its spectrum is similar to viriconazole. It is active against molds and yeast such as Candida albicans, Aspergillus, and Cryptococcus. It also has good activity agaisnt dermatophytes. It has limited activity against Fusarium, Scedosporium, and Zygomycetes. It has activity against T. cruzi, the causal agent of Chagas disease. |
| Microbiology Applications |
Ravuconazole has potent activity against a wide range of fungi. In an experimental model or oral candidiasis in rats, the compound reduced the numbers of CFU in oral swabs compared to controls (P<0.05) and was more effective than itraconazole and as effective as fluconazole. Thus, it has efficacy in murine aspergillosis, candidiasis, and cryptococcus models (Hata et al, 1996). Cross-resistance can be a concern in the azole family of compounds. |
| Molecular Formula | C22H17F2N5O6 |
| References |
1996) In vitro and in vivo antifungal activities of ER-30346, a novel oral triazole with a broad antifungal spectrum. Antimicrob. Agents Chemother. 40(10):2237-2242 PMID 8891121 Hata K et al (1996) Efficacy of ER-30346, a novel oral triazole antifungal agent, in experimental models of aspergillosis, candidiasis, and cryptococcosis. Antimicrob Agents Chemother. 40(10):2243-2247 PMID 8891122 Pasqualotto AC, Thiele KO, Goldani LZ (2010) Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. Curr. Opin. Investig. Drugs. 11(2):165-174 PMID 20112166 Yasutsugu U et al (2003) Phosphonooxymethyl prodrugs of the broad spectrum antifungal azole, ravuconazole: Synthesis and biological properties. Bioorganic and Medicinal Chem. Lett. 13(21):3669-3672 |