Ravuconazole

Summary

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]

Ravuconazole
Ravuconazole.svg
Clinical data
ATC code
  • None
Identifiers
  • 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 checkY
PubChem CID
  • 467825
ChemSpider
  • 411041 ☒N
UNII
  • 95YH599JWV
ChEBI
  • CHEBI:143825
ChEMBL
  • ChEMBL294029 ☒N
NIAID ChemDB
  • 057176
CompTox Dashboard (EPA)
  • DTXSID40171329 Edit this at Wikidata
Chemical and physical data
FormulaC22H17F2N5OS
Molar mass437.47 g·mol−1
3D model (JSmol)
  • Interactive image
  • C[C@@H](c1nc(-c2ccc(C#N)cc2)cs1)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
  • 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
 ☒NcheckY (what is this?)  (verify)

See alsoEdit

ReferencesEdit

  1. ^ "Ravuconazole". AdisInsight. Retrieved 12 November 2017.
  2. ^ The Aspergillus Website, Pasqualotto AC, Denning DW. Ravuconazole. Date accessed: 2010 Feb 18.
  3. ^ Pasqualotto AC, Thiele KO, Goldani LZ (2010). "Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole". Curr Opin Investig Drugs. 11 (2): 165–74. PMID 20112166.
  4. ^ Pfaller, M. A.; Messer, S. A.; Hollis, R. J.; Jones, R. N.; Sentry Participants, Group (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): 1032–7. doi:10.1128/AAC.46.4.1032-1037.2002. PMC 127116. PMID 11897586.