Ravuconazole
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MedKoo CAT#: 526101

CAS#: 182760-06-1

Description: Ravuconazole, also known as BMS-207147; ER-30346 ; ER-30346, is a potent triazole antifungal. Ravuconazole is currently in phase I/II clinical trials. Ravuconazole has shown to have a similar spectrum of activity to voriconazole, with an increased half-life.

Chemical Structure

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Ravuconazole
CAS# 182760-06-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 526101
Name: Ravuconazole
CAS#: 182760-06-1
Chemical Formula: C22H17F2N5OS
Exact Mass: 437.11
Molecular Weight: 437.470
Elemental Analysis: C, 60.40; H, 3.92; F, 8.69; N, 16.01; O, 3.66; S, 7.33

Price and Availability

Size Price Availability Quantity
5mg USD 250 2 Weeks
10mg USD 400 2 Weeks
25mg USD 750
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Synonym: Ravuconazole; BMS-207147; ER-30346 ; ER-30346; BMS207147; ER30346 ; ER30346.

IUPAC/Chemical Name: p-(2-((alphaR,betaR)-2,4-Difluoro-beta-hydroxy-alpha-methyl-beta-(1H-1,2,4-triazol-1-ylmethyl)phenethyl)-4-thiazolyl)benzonitrile

InChi Key: OPAHEYNNJWPQPX-RCDICMHDSA-N

InChi Code: 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

SMILES Code: N#CC1=CC=C(C2=CSC([C@H](C)[C@@](CN3N=CN=C3)(O)C4=CC=C(F)C=C4F)=N2)C=C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, DMF, and ethanol

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO, DMF, and ethanol

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot#A21O07B12
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Ravuconazole (BMS-207147) is a potent and broad spectrum triazole antifungal. Ravuconazole is an inhibitor of sterol biosynthesis by inhibition of cytochrome P450 14α-demethylase, an enzyme in the sterol biosynthesis pathway that leads from lanosterol to ergosterol.
In vitro activity: The minimum inhibitory concentration (MIC) values of ravuconazole and isavuconazole were lower than itraconazole’s, voriconazole’s, and posaconazole’s. Ravuconazole and isavuconazole appear to be more efficient against most dematiaceous fungal infections than the other triazoles tested. Reference: Antimicrob Agents Chemother. 2020 Aug 20;64(9):e00643-20. https://pubmed.ncbi.nlm.nih.gov/32571811/
In vivo activity: Ravuconazole treatment in SCID mice cleared infection in all tissues from 50% of mice. Ravuconazole has good efficacy and the potential to cure mucosal candidosis in the absence of a functional immune response. Reference: Antimicrob Agents Chemother. 2001 Dec;45(12):3433-6. https://pubmed.ncbi.nlm.nih.gov/11709320/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 20.0 45.72
DMF 25.0 57.15
Ethanol 5.0 11.43

Preparing Stock Solutions

The following data is based on the product molecular weight 437.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zheng H, Song N, Mei H, Dong J, Li D, Li X, Liu W. In Vitro Activities of Ravuconazole and Isavuconazole against Dematiaceous Fungi. Antimicrob Agents Chemother. 2020 Aug 20;64(9):e00643-20. doi: 10.1128/AAC.00643-20. PMID: 32571811; PMCID: PMC7449202. 2. Dong J, Liang G, Zheng H, Kan S, Song N, Zhang M, Liu W. In Vitro activity of ravuconazole against Candida auris and vaginal candida isolates. Mycoses. 2021 Jun;64(6):651-655. doi: 10.1111/myc.13260. Epub 2021 Mar 5. PMID: 33609301. 3. Andes D, Marchillo K, Stamstad T, Conklin R. In vivo pharmacodynamics of a new triazole, ravuconazole, in a murine candidiasis model. Antimicrob Agents Chemother. 2003 Apr;47(4):1193-9. doi: 10.1128/AAC.47.4.1193-1199.2003. PMID: 12654646; PMCID: PMC152484. 4. Clemons KV, Stevens DA. Efficacy of ravuconazole in treatment of mucosal candidosis in SCID mice. Antimicrob Agents Chemother. 2001 Dec;45(12):3433-6. doi: 10.1128/AAC.45.12.3433-3436.2001. PMID: 11709320; PMCID: PMC90849.
In vitro protocol: 1. Zheng H, Song N, Mei H, Dong J, Li D, Li X, Liu W. In Vitro Activities of Ravuconazole and Isavuconazole against Dematiaceous Fungi. Antimicrob Agents Chemother. 2020 Aug 20;64(9):e00643-20. doi: 10.1128/AAC.00643-20. PMID: 32571811; PMCID: PMC7449202. 2. Dong J, Liang G, Zheng H, Kan S, Song N, Zhang M, Liu W. In Vitro activity of ravuconazole against Candida auris and vaginal candida isolates. Mycoses. 2021 Jun;64(6):651-655. doi: 10.1111/myc.13260. Epub 2021 Mar 5. PMID: 33609301.
In vivo protocol: 1. Andes D, Marchillo K, Stamstad T, Conklin R. In vivo pharmacodynamics of a new triazole, ravuconazole, in a murine candidiasis model. Antimicrob Agents Chemother. 2003 Apr;47(4):1193-9. doi: 10.1128/AAC.47.4.1193-1199.2003. PMID: 12654646; PMCID: PMC152484. 2. Clemons KV, Stevens DA. Efficacy of ravuconazole in treatment of mucosal candidosis in SCID mice. Antimicrob Agents Chemother. 2001 Dec;45(12):3433-6. doi: 10.1128/AAC.45.12.3433-3436.2001. PMID: 11709320; PMCID: PMC90849.

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1: Ahmed SA, Kloezen W, Duncanson F, Zijlstra EE, de Hoog GS, Fahal AH, van de Sande WW. Madurella mycetomatis is highly susceptible to ravuconazole. PLoS Negl Trop Dis. 2014 Jun 19;8(6):e2942. doi: 10.1371/journal.pntd.0002942. eCollection 2014 Jun. PubMed PMID: 24945848; PubMed Central PMCID: PMC4063742.

2: Yamaguchi H, Ikeda F, Iyoda T, Suzuki M, Mikawa T. [In vitro antifungal activity of ravuconazole against isolates of dermatophytes and Candida species from patients with dermatomycoses]. Med Mycol J. 2014;55(4):J157-63. doi: 10.3314/mmj.55.J157. Japanese. PubMed PMID: 25742996.

3: Elizondo-Zertuche M, Robledo-Leal E, González JG, Ceceñas LA, González GM. Efficacy of ravuconazole in a murine model of vaginitis by Candida albicans. Rev Iberoam Micol. 2015 Jan-Mar;32(1):30-3. doi: 10.1016/j.riam.2013.09.006. Epub 2013 Sep 23. PubMed PMID: 24071640.

4: Watt K, Manzoni P, Cohen-Wolkowiez M, Rizzollo S, Boano E, Jacqz-Aigrain E, Benjamin DK. Triazole use in the nursery: fluconazole, voriconazole, posaconazole, and ravuconazole. Curr Drug Metab. 2013 Feb;14(2):193-202. Review. PubMed PMID: 22935068; PubMed Central PMCID: PMC3541435.

5: Gaikwad ND, Patil SV, Bobade VD. Hybrids of ravuconazole: synthesis and biological evaluation. Eur J Med Chem. 2012 Aug;54:295-302. doi: 10.1016/j.ejmech.2012.05.010. Epub 2012 May 15. PubMed PMID: 22652223.

6: Diniz Lde F, Caldas IS, Guedes PM, Crepalde G, de Lana M, Carneiro CM, Talvani A, Urbina JA, Bahia MT. Effects of ravuconazole treatment on parasite load and immune response in dogs experimentally infected with Trypanosoma cruzi. Antimicrob Agents Chemother. 2010 Jul;54(7):2979-86. doi: 10.1128/AAC.01742-09. Epub 2010 Apr 19. PubMed PMID: 20404124; PubMed Central PMCID: PMC2897273.

7: Pasqualotto AC, Thiele KO, Goldani LZ. Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. Curr Opin Investig Drugs. 2010 Feb;11(2):165-74. Review. PubMed PMID: 20112166.

8: Demchok JP, Meletiadis J, Roilides E, Walsh TJ. Comparative pharmacodynamic interaction analysis of triple combinations of caspofungin and voriconazole or ravuconazole with subinhibitory concentrations of amphotericin B against Aspergillus spp. Mycoses. 2010 May;53(3):239-45. doi: 10.1111/j.1439-0507.2009.01700.x. Epub 2009 Mar 7. PubMed PMID: 19389068.

9: Knipe JO, Mosure KW. Nonclinical pharmacokinetics of BMS-292655, a water-soluble prodrug of the antifungal ravuconazole. Biopharm Drug Dispos. 2008 Jul;29(5):270-9. doi: 10.1002/bdd.612. PubMed PMID: 18548464.

10: Yan JH, Marino MR, Smith RA, Kanamaluru V, O'Mara EM, Grasela DM. The effect of ravuconazole on the pharmacokinetics of nelfinavir in healthy male volunteers. J Clin Pharmacol. 2006 Feb;46(2):193-200. PubMed PMID: 16432271.

11: Cuenca-Estrella M, Gomez-Lopez A, Mellado E, Garcia-Effron G, Monzon A, Rodriguez-Tudela JL. In vitro activity of ravuconazole against 923 clinical isolates of nondermatophyte filamentous fungi. Antimicrob Agents Chemother. 2005 Dec;49(12):5136-8. PubMed PMID: 16304186; PubMed Central PMCID: PMC1315962.

12: Groll AH, Mickiene D, Petraitis V, Petraitiene R, Kelaher A, Sarafandi A, Wuerthwein G, Bacher J, Walsh TJ. Compartmental pharmacokinetics and tissue distribution of the antifungal triazole ravuconazole following intravenous administration of its di-lysine phosphoester prodrug (BMS-379224) in rabbits. J Antimicrob Chemother. 2005 Nov;56(5):899-907. Epub 2005 Sep 19. PubMed PMID: 16172108.

13: Gupta AK, Leonardi C, Stoltz RR, Pierce PF, Conetta B; Ravuconazole onychomycosis group. A phase I/II randomized, double-blind, placebo-controlled, dose-ranging study evaluating the efficacy, safety and pharmacokinetics of ravuconazole in the treatment of onychomycosis. J Eur Acad Dermatol Venereol. 2005 Jul;19(4):437-43. PubMed PMID: 15987289.

14: Gupta AK, Kohli Y, Batra R. In vitro activities of posaconazole, ravuconazole, terbinafine, itraconazole and fluconazole against dermatophyte, yeast and non-dermatophyte species. Med Mycol. 2005 Mar;43(2):179-85. PubMed PMID: 15832561.

15: Pfaller MA, Espinel-Ingroff A, Jones RN. Clinical evaluation of the Sensititre YeastOne colorimetric antifungal plate for antifungal susceptibility testing of the new triazoles voriconazole, posaconazole, and ravuconazole. J Clin Microbiol. 2004 Oct;42(10):4577-80. PubMed PMID: 15472311; PubMed Central PMCID: PMC522344.

16: Cuenca-Estrella M, Gomez-Lopez A, Mellado E, Garcia-Effron G, Rodriguez-Tudela JL. In vitro activities of ravuconazole and four other antifungal agents against fluconazole-resistant or -susceptible clinical yeast isolates. Antimicrob Agents Chemother. 2004 Aug;48(8):3107-11. PubMed PMID: 15273127; PubMed Central PMCID: PMC478504.

17: Pfaller MA, Messer SA, Boyken L, Rice C, Tendolkar S, Hollis RJ, Diekema DJ. Cross-resistance between fluconazole and ravuconazole and the use of fluconazole as a surrogate marker to predict susceptibility and resistance to ravuconazole among 12,796 clinical isolates of Candida spp. J Clin Microbiol. 2004 Jul;42(7):3137-41. PubMed PMID: 15243072; PubMed Central PMCID: PMC446250.

18: Petraitiene R, Petraitis V, Lyman CA, Groll AH, Mickiene D, Peter J, Bacher J, Roussillon K, Hemmings M, Armstrong D, Avila NA, Walsh TJ. Efficacy, safety, and plasma pharmacokinetics of escalating dosages of intravenously administered ravuconazole lysine phosphoester for treatment of experimental pulmonary aspergillosis in persistently neutropenic rabbits. Antimicrob Agents Chemother. 2004 Apr;48(4):1188-96. PubMed PMID: 15047519; PubMed Central PMCID: PMC375262.

19: Pfaller MA, Diekema DJ, Messer SA, Boyken L, Hollis RJ, Jones RN. In vitro susceptibilities of rare Candida bloodstream isolates to ravuconazole and three comparative antifungal agents. Diagn Microbiol Infect Dis. 2004 Feb;48(2):101-5. PubMed PMID: 14972378.

20: Minassian B, Huczko E, Washo T, Bonner D, Fung-Tomc J. In vitro activity of ravuconazole against Zygomycetes, Scedosporium and Fusarium isolates. Clin Microbiol Infect. 2003 Dec;9(12):1250-2. PubMed PMID: 14686996.