MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 526101 | Name: Ravuconazole
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Ravuconazole
Ravuconazole
CAS#182760-06-1

Theoretical Analysis

MedKoo Cat#: 526101

Name: Ravuconazole

CAS#: 182760-06-1

Chemical Formula: C22H17F2N5OS

Exact Mass: 437.1122

Molecular Weight: 437.47

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 250.00 2 Weeks
10mg USD 400.00 2 Weeks
25mg USD 750.00
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
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/
Solvent mg/mL mM
Solubility
DMSO 20.0 45.72
DMF 25.0 57.15
Ethanol 5.0 11.43
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Tsunemi Y, Naka W. Exploratory study on short-term administration of oral fosravuconazole for tinea pedis. J Dermatol. 2024 Sep 10. doi: 10.1111/1346-8138.17455. Epub ahead of print. PMID: 39254317. 2: Torchelsen FKVDS, Fernandes TCP, Sousa SMR, Sales-Junior PA, Branquinho RT, Murta SMF, Teixeira RR, Mosqueira VCF, Lana M. Screening of synthetic 1,2,3-triazolic compounds inspired by SRPIN340 as anti-Trypanosoma cruzi agents. Rev Soc Bras Med Trop. 2024 Jul 29;57:e00411. doi: 10.1590/0037-8682-0585-2023. PMID: 39082521; PMCID: PMC11290850. 3: Deng X, Song CC, Gu WJ, Wang YJ, Feng L, Zhou XJ, Zhou MQ, Yuan WC, Chen YZ. Regioselective and enantioselective propargylic hydroxylations catalyzed by P450tol monooxygenases. Bioresour Bioprocess. 2024 Jul 2;11(1):64. doi: 10.1186/s40643-024-00771-7. PMID: 38954282; PMCID: PMC11219674. 4: Bisio MMC, Jurado Medina LS, García-Bournissen F, Gulin JEN. Listen to what the animals say: a systematic review and meta-analysis of sterol 14-demethylase inhibitor efficacy for in vivo models of Trypanosoma cruzi infection. Parasitol Res. 2024 Jun 21;123(6):248. doi: 10.1007/s00436-024-08257-3. PMID: 38904688. 5: Ramos LG, de Souza KR, Júnior PAS, Câmara CC, Castelo-Branco FS, Boechat N, Carvalho SA. Tackling the challenges of human Chagas disease: A comprehensive review of treatment strategies in the chronic phase and emerging therapeutic approaches. Acta Trop. 2024 Aug;256:107264. doi: 10.1016/j.actatropica.2024.107264. Epub 2024 May 26. PMID: 38806090. 6: Álvarez-Pérez S, Quevedo-Caraballo S, García ME, Blanco JL. Prevalence and genetic diversity of azole-resistant Malassezia pachydermatis isolates from canine otitis and dermatitis: A 2-year study. Med Mycol. 2024 May 3;62(5):myae053. doi: 10.1093/mmy/myae053. PMID: 38734886. 7: Hiruma J, Nojyo H, Harada K, Kano R. Development of treatment strategies by comparing the minimum inhibitory concentrations and minimum fungicidal concentrations of azole drugs in dermatophytes. J Dermatol. 2024 May 7. doi: 10.1111/1346-8138.17241. Epub ahead of print. PMID: 38712872. 8: Okubo A, Hanada M, Kodama S, Taniguchi N, Miyazaki Y. Long-term follow-up study of the efficacy of fosravuconazole in the treatment of onychomycosis in elderly patients. J Dermatol. 2024 Aug;51(8):1091-1097. doi: 10.1111/1346-8138.17254. Epub 2024 May 3. PMID: 38700273. 9: Tang Y, Li Z, Zeng M, Li R, Song H, Zhang D, Xue F, Qin Y. Asymmetric Synthesis of Triazole Antifungal Agents Enabled by an Upgraded Strategy for the Key Epoxide Intermediate. J Org Chem. 2024 Apr 5;89(7):4971-4978. doi: 10.1021/acs.joc.4c00193. Epub 2024 Mar 20. PMID: 38509452. 10: Naka W, Tsunemi Y. Effects of additional oral fosravuconazole l-lysine ethanolate therapy following inadequate response to initial treatment for onychomycosis: A multicenter, randomized controlled trial. J Dermatol. 2024 Jul;51(7):964-972. doi: 10.1111/1346-8138.17193. Epub 2024 Mar 14. PMID: 38482989. 11: Nojo H, Hiruma J, Noguchi H, Hiruma M, Harada K, Makimura K, Kano R. In vitro Azole Susceptibility Testing of Japanese Isolates of Itraconazole- Resistant Dermatophytes. Med Mycol J. 2023;64(4):103-105. doi: 10.3314/mmj.23-00005. PMID: 38030274. 12: Pfarr KM, Krome AK, Al-Obaidi I, Batchelor H, Vaillant M, Hoerauf A, Opoku NO, Kuesel AC. The pipeline for drugs for control and elimination of neglected tropical diseases: 2. Oral anti-infective drugs and drug combinations for off- label use. Parasit Vectors. 2023 Oct 31;16(1):394. doi: 10.1186/s13071-023-05909-8. PMID: 37907954; PMCID: PMC10619278. 13: Song G, Kong X, Li X, Liu W, Liang G. Prior selection of itraconazole in the treatment of recalcitrant Trichophyton indotineae infection: Real-world results from retrospective analysis. Mycoses. 2024 Jan;67(1):e13663. doi: 10.1111/myc.13663. Epub 2023 Oct 26. PMID: 37882456. 14: Davari A, Hedayati MT, Jafarzadeh J, Nikmanesh B, Nabili M, Hamidieh AA, Abastabar M, Ahmadi N, Al-Hatmi AMS, Moazeni M. Evaluation of Candida colonization index, molecular identification, and antifungal susceptibility pattern of Candida species isolated from critically ill pediatric patients: A single-center study in Iran. Curr Med Mycol. 2022 Dec;8(4):15-21. doi: 10.32598/CMM.2023.1372. PMID: 37736608; PMCID: PMC10509495. 15: Chaudhary J, Jain A, Dhingra A, Chopra B, Sharma V, Gupta J, Kaushik A. 1,3-thiazole Derivatives: A Scaffold with Considerable Potential in the Treatment of Neurodegenerative Diseases. Curr Top Med Chem. 2023;23(23):2185-2196. doi: 10.2174/1568026623666230719124850. PMID: 37469159. 16: Inoue T, Watabe D, Tsunemi Y, Amano H. Outcome of fosravuconazole treatment for onychomycosis refractory to topical antifungal agents. J Dermatol. 2023 Aug;50(8):1014-1019. doi: 10.1111/1346-8138.16824. Epub 2023 May 8. PMID: 37157898. 17: Proskurnicka A, Żupnik K, Bakuła Z, Iskra M, Rösler U, Jagielski T. Drug Susceptibility Profiling of Prototheca Species Isolated from Cases of Human Protothecosis. Antimicrob Agents Chemother. 2023 Apr 18;67(4):e0162722. doi: 10.1128/aac.01627-22. Epub 2023 Mar 21. PMID: 36943065; PMCID: PMC10112244. 18: Hiruma J, Noguchi H, Shimizu T, Hiruma M, Harada K, Kano R. Epidemiological study of antifungal-resistant dermatophytes isolated from Japanese patients. J Dermatol. 2023 Aug;50(8):1068-1071. doi: 10.1111/1346-8138.16780. Epub 2023 Mar 20. PMID: 36938668. 19: Nandurkar Y, Shinde A, Bhoye MR, Jagadale S, Mhaske PC. Synthesis and Biological Screening of New 2-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-4-aryl Thiazole Derivatives as Potential Antimicrobial Agents. ACS Omega. 2023 Feb 22;8(9):8743-8754. doi: 10.1021/acsomega.2c08137. PMID: 36910954; PMCID: PMC9996765. 20: Hiruma J, Kimura U, Noguchi H, Hiruma M, Harada K, Kano R. In vitro Azole Susceptibility Testing of Japanese Isolates of Terbinafine-Resistant Trichophyton indotineae and Trichophyton rubrum. Med Mycol J. 2023;64(1):23-25. doi: 10.3314/mmj.22-00021. PMID: 36858630.