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^Y
PubChem (CID)	467825
ChemSpider	411041^N
UNII	95YH599JWV^N
ChEMBL	CHEMBL294029^N
NIAID ChemDB	057176
Chemical and physical data
Formula	C₂₂H₁₇F₂N₅OS
Molar mass	437.465086 g/mol
3D model (Jmol)	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^N Key:OPAHEYNNJWPQPX-RCDICMHDSA-N^N
^NY (what is this?) (verify)

Ravuconazole (codenamed 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.
↑ 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.

Antifungals (D01 and J02)

Wall/
membrane

Ergosterol
inhibitors

Azoles
(lanosterol 14
alpha-demethylase inhibitors)

Imidazoles	Topical: bifonazole^‡ butoconazole chlormidazole^‡ clotrimazole^# croconazole^‡ econazole fenticonazole^‡ flutrimazole isoconazole^‡ ketoconazole luliconazole miconazole^# neticonazole^‡ omoconazole^‡ oxiconazole sertaconazole sulconazole tioconazole Systemic: ketoconazole

Triazoles	Topical: efinaconazole fluconazole^# fosfluconazole terconazole Systemic: fluconazole^# hexaconazole^‡ isavuconazole itraconazole 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	flucytosine^#

Mitotic inhibitors	griseofulvin^#

Aminoacyl tRNA synthetase inhibitors	tavaborole

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Ravuconazole

See also

References