Ravuconazole

Ravuconazole
Clinical data
ATC code	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 ;
PubChem CID	467825;
ChemSpider	411041 ;
UNII	95YH599JWV;
ChEMBL	ChEMBL294029 ;
NIAID ChemDB	057176;
CompTox Dashboard (EPA)	DTXSID40171329 ;
Chemical and physical data
Formula	C22H17F2N5OS
Molar mass	437.465086 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H](C1=NC(=CS1)C2=CC=C(C=C2)C#N)[C@](CN3C=NC=N3)(C4=C(C=C(C=C4)F)F)O;
	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 ; Key:OPAHEYNNJWPQPX-RCDICMHDSA-N ;
	(what is this?) (verify)

Ravuconazole (BMS-207147 and ER-30346) is a potent triazole antifungal, being developed by Bristol-Myers Squibb, that is currently in phase I/II clinical trials.^[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

^ National Cancer Institute. Ravuconazole in Preventing Fungal Infections in Patients Undergoing Allogeneic Stem Cell Transplantation. In: ClinicalTrials.gov [Internet]. Bethesda (MD): National Library of Medicine (US). 2000- [cited 2010 Feb 18]. Available from: http://clinicaltrials.gov/ct2/show/NCT00064311?term=ravuconazole&spons_ex=Y&rank=1 NLM Identifier: NCT00064311.
^ The Aspergillus Website, Pasqualotto AC, Denning DW. Ravuconazole. Date accessed: 2010 Feb 18.
^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ 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.

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[1] National Cancer Institute. Ravuconazole in Preventing Fungal Infections in Patients Undergoing Allogeneic Stem Cell Transplantation. In: ClinicalTrials.gov [Internet]. Bethesda (MD): National Library of Medicine (US). 2000- [cited 2010 Feb 18]. Available from: http://clinicaltrials.gov/ct2/show/NCT00064311?term=ravuconazole&spons_ex=Y&rank=1 NLM Identifier: NCT00064311.

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.

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