Ravuconazole

Chemical compound

None

Identifiers

IUPAC name

4-[2-[(2R,3R)-3-(2,4-Difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-1,3-thiazol-4-yl]benzonitrile

CAS Number

182760-06-1^Y

PubChem CID

467825

ChemSpider

411041^N

UNII

95YH599JWV

ChEBI

CHEBI:143825

ChEMBL

ChEMBL294029^N

NIAID ChemDB

057176

CompTox Dashboard (EPA)

DTXSID40171329

Chemical and physical dataFormulaC₂₂H₁₇F₂N₅OSMolar mass437.47 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F

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^N
Key:OPAHEYNNJWPQPX-RCDICMHDSA-N^N

^NY (what is this?) (verify)

Ravuconazole (codenamed BMS-207147 and ER-30346) is a potent triazole antifungal, the development of which was discontinued in 2007.^[1] The drug has shown to have a similar spectrum of activity to voriconazole, with an increased half-life.^[2] However, ravuconazole has limited activity against species of Fusarium, Scedosporium, and Zygomycetes.^[3]^[4]

References

^ "Ravuconazole". AdisInsight. Springer Nature Switzerland AG. Retrieved 12 November 2017.
^ Pasqualotto AC, Denning DW. "Ravuconazole". The Aspergillus Website. Retrieved 18 February 2010.
^ Pasqualotto AC, Thiele KO, Goldani LZ (February 2010). "Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole". Current Opinion in Investigational Drugs. 11 (2): 165–174. PMID 20112166.
^ Pfaller MA, Messer SA, Hollis RJ, Jones RN (April 2002). "Antifungal activities of posaconazole, ravuconazole, and voriconazole compared to those of itraconazole and amphotericin B against 239 clinical isolates of Aspergillus spp. and other filamentous fungi: report from SENTRY Antimicrobial Surveillance Program, 2000". Antimicrobial Agents and Chemotherapy. 46 (4): 1032–1037. doi:10.1128/AAC.46.4.1032-1037.2002. PMC 127116. PMID 11897586.

External links

Media related to Ravuconazole at Wikimedia Commons

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles (lanosterol 14α-
demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ climbazole clotrimazole^# croconazole^‡ eberconazole econazole fenticonazole^‡ flutrimazole isoconazole ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole
Triazoles	Topical: efinaconazole fluconazole^# terconazole Systemic: fluconazole^# fosfluconazole fosravuconazole hexaconazole^‡ isavuconazole itraconazole^# oteseconazole posaconazole voriconazole^# Unknown: albaconazole^‡ ravuconazole^†
Thiazoles	Topical: abafungin^‡

Polyene antimycotics
(ergosterol binding)

Topical: hamycin^‡
natamycin
nystatin^#
Systemic: amphotericin B^#, hamycin^‡

Squalene monooxygenase
inhibitors

Allylamines	Topical: naftifine terbinafine Systemic: terbinafine
Benzylamines	Topical: butenafine

Others

Topical: amorolfine

β-glucan synthase
inhibitors

Intracellular

Pyrimidine analogues/ thymidylate synthase inhibitors	Systemic: flucytosine^#
Mitotic inhibitors	Systemic: griseofulvin^#
Aminoacyl tRNA synthetase inhibitors	Topical: tavaborole