Beclabuvir | CAS# 958002-33-0 | Antiviral

MedKoo Cat#: 574302 | Name: Beclabuvir

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Description:

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

Beclabuvir is an antiviral drug for the treatment of hepatitis C virus (HCV) infection.

Chemical Structure

Beclabuvir

CAS#958002-33-0 (free base)

Theoretical Analysis

MedKoo Cat#: 574302

Name: Beclabuvir

CAS#: 958002-33-0 (free base)

Chemical Formula: C36H45N5O5S

Exact Mass: 659.3141

Molecular Weight: 659.85

Elemental Analysis: C, 65.53; H, 6.87; N, 10.61; O, 12.12; S, 4.86

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 750.00	2 Weeks
10mg	USD 1,250.00	2 Weeks

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Related CAS #

958002-36-3 (HCl) 958002-33-0 (free base)

Synonym

Beclabuvir, BMS-791325, BCV

IUPAC/Chemical Name

(8S,10R)-19-cyclohexyl-N-(dimethylsulfamoyl)-5-methoxy-10-(3-methyl-3,8-diazabicyclo[3.2.1]octane-8-carbonyl)-12-azapentacyclo[10.7.0.02,7.08,10.013,18]nonadeca-1(19),2(7),3,5,13(18),14,16-heptaene-15-carboxamide Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

InChi Key

ZTTKEBYSXUCBSE-VSBZUFFNSA-N

InChi Code

InChI=1S/C36H45N5O5S/c1-38(2)47(44,45)37-34(42)23-10-14-28-31(16-23)40-21-36(35(43)41-24-11-12-25(41)20-39(3)19-24)18-30(36)29-17-26(46-4)13-15-27(29)33(40)32(28)22-8-6-5-7-9-22/h10,13-17,22,24-25,30H,5-9,11-12,18-21H2,1-4H3,(H,37,42)/t24?,25?,30-,36-/m0/s1

SMILES Code

CN1CC2CCC(C1)N2C(=O)C34CC3C5=C(C=CC(=C5)OC)C6=C(C7=C(N6C4)C=C(C=C7)C(=O)NS(=O)(=O)N(C)C)C8CCCCC8

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

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Instruction

View handling instruction

Biological target:

Beclabuvir is an inhibitor that binds to thumb site 1 of the hepatitis C virus (HCV) NS5B RNA-dependent RNA polymerase and inhibits recombinant NS5B proteins from HCV genotypes 1, 3, 4, and 5 with IC50 of < 28 nM.

In vitro activity:

TBD

In vivo activity:

The efficacy of daclatasvir (DCV)/asunaprevir (ASV)/beclabuvir (BCV) treatment was evaluated in HCV-infected mice. Human hepatocyte chimaeric mice were injected with serum samples obtained from either a DAA-naïve patient or a DCV/ASV treatment failure and were then treated with DCV/ASV alone or in combination with BCV for 4 weeks. DCV/ASV treatment successfully eliminated the virus in DAA-naïve-patient HCV-infected mice. DCV/ASV treatment failure HCV-infected mice developed viral breakthrough during DCV/ASV treatment, with the emergence of NS5A-L31V/Y93H HCV resistance-associated variants (RAVs) being observed by direct sequencing. DCV/ASV/BCV treatment inhibited viral breakthrough in NS5A-L31V/Y93H-mutated HCV-infected mice, but HCV relapsed with the emergence of NS5B-P495S variants after the cessation of the treatment. Reference: J Gen Virol. 2018 Aug;99(8):1058-1065. https://www.microbiologyresearch.org/content/journal/jgv/10.1099/jgv.0.001091#tab2

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	45.46

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 659.85 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.

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. Teraoka Y, Uchida T, Imamura M, Hiraga N, Osawa M, Kan H, Saito Y, Tsuge M, Abe-Chayama H, Hayes CN, Makokha GN, Aikata H, Miki D, Ochi H, Ishida Y, Tateno C, Chayama K. Limitations of daclatasvir/asunaprevir plus beclabuvir treatment in cases of NS5A inhibitor treatment failure. J Gen Virol. 2018 Aug;99(8):1058-1065. doi: 10.1099/jgv.0.001091. Epub 2018 Jun 19. PMID: 29916799.

In vitro protocol:

TBD

In vivo protocol:

1: Gentile I, Zappulo E, Buonomo AR, Maraolo AE, Borgia G. Beclabuvir for the treatment of hepatitis C. Expert Opin Investig Drugs. 2015;24(8):1111-21. doi: 10.1517/13543784.2015.1059820. Epub 2015 Jul 9. PMID: 26156630. 2: Thiam A, Conway B. Daclatasvir, asunaprevir and beclabuvir fixed-dose combination for patients with genotype 1 chronic hepatitis C. Drugs Today (Barc). 2018 Apr;54(4):237-244. doi: 10.1358/dot.2018.54.4.2795154. PMID: 29869645. 3: Zappulo E, Scotto R, Buonomo AR, Maraolo AE, Pinchera B, Gentile I. Efficacy and safety of a fixed dose combination tablet of asunaprevir + beclabuvir + daclatasvir for the treatment of Hepatitis C. Expert Opin Pharmacother. 2020 Feb;21(3):261-273. doi: 10.1080/14656566.2019.1697674. Epub 2020 Jan 8. PMID: 31914336. 4: Esposito I, Marciano S, Trinks J. Pharmacokinetic and pharmacodynamic evaluation of daclatasvir, asunaprevir plus beclabuvir as a fixed-dose co- formulation for the treatment of hepatitis C. Expert Opin Drug Metab Toxicol. 2018 Jun;14(6):649-657. doi: 10.1080/17425255.2018.1483336. Epub 2018 Jun 10. PMID: 29855221. 5: Osawa M, Ueno T, Shiozaki T, Ishikawa H, Li H, Garimella T. Population Pharmacokinetic Analysis of Daclatasvir, Asunaprevir, and Beclabuvir Combination in HCV-Infected Subjects. Clin Pharmacol Drug Dev. 2019 Aug;8(6):802-817. doi: 10.1002/cpdd.649. Epub 2019 Jan 10. PMID: 30629858. 6: Ye Q, Huang Y, Grier S, Miller SA. Oxidative degradation pathways of beclabuvir hydrochloride mediated by hydrogen peroxide and UV/Vis light. J Pharm Biomed Anal. 2019 Aug 5;172:388-394. doi: 10.1016/j.jpba.2019.05.017. Epub 2019 May 8. PMID: 31100536. 7: Ahmed AM, Doheim MF, Mattar OM, Sherif NA, Truong DH, Hoa PTL, Hirayama K, Huy NT. Beclabuvir in combination with asunaprevir and daclatasvir for hepatitis C virus genotype 1 infection: A systematic review and meta-analysis. J Med Virol. 2018 May;90(5):907-918. doi: 10.1002/jmv.24947. Epub 2018 Feb 1. PMID: 28892235. 8: Tatum H, Thuluvath PJ, Lawitz E, Martorell C, DeMicco M, Cohen S, Rustgi V, Ravendhran N, Ghalib R, Hanson J, Zamparo J, Zhao J, Cooney E, Treitel M, Hughes E. A randomized, placebo-controlled study of the NS5B inhibitor beclabuvir with peginterferon/ribavirin for HCV genotype 1. J Viral Hepat. 2015 Aug;22(8):658-64. doi: 10.1111/jvh.12372. Epub 2014 Dec 15. PMID: 25496007. 9: Osawa M, Ueno T, Shiozaki T, Li H, Garimella T. Safety Exposure-Response Analysis for Daclatasvir, Asunaprevir, and Beclabuvir Combinations in HCV- Infected Subjects. J Clin Pharmacol. 2019 Apr;59(4):557-565. doi: 10.1002/jcph.1347. Epub 2018 Dec 19. PMID: 30566237; PMCID: PMC6590348. 10: Ueno T, Osawa M, Shiozaki T, Green M, Garimella T. Exposure-Response Analysis for Efficacy of Daclatasvir, Asunaprevir, and Beclabuvir Combinations in HCV-Infected Patients. Clin Pharmacol Drug Dev. 2019 Oct;8(7):903-913. doi: 10.1002/cpdd.646. Epub 2019 Jan 22. PMID: 30667592. 11: Jiang H, Titsch C, Zeng J, Jones B, Joyce P, Gandhi Y, Turley W, Burrell R, Aubry AF, Arnold ME. Overcoming interference with the detection of a stable isotopically labeled microtracer in the evaluation of beclabuvir absolute bioavailability using a concomitant microtracer approach. J Pharm Biomed Anal. 2017 Sep 5;143:9-16. doi: 10.1016/j.jpba.2017.04.030. Epub 2017 May 17. PMID: 28544885. 12: Toyota J, Karino Y, Suzuki F, Ikeda F, Ido A, Tanaka K, Takaguchi K, Naganuma A, Tomita E, Chayama K, Fujiyama S, Inada Y, Yoshiji H, Watanabe H, Ishikawa H, Hu W, McPhee F, Linaberry M, Yin PD, Swenson ES, Kumada H. Daclatasvir/asunaprevir/beclabuvir fixed-dose combination in Japanese patients with HCV genotype 1 infection. J Gastroenterol. 2017 Mar;52(3):385-395. doi: 10.1007/s00535-016-1245-6. Epub 2016 Aug 9. PMID: 27502287. 13: Everson GT, Sims KD, Thuluvath PJ, Lawitz E, Hassanein T, Rodriguez-Torres M, Desta T, Hawkins T, Levin JM, Hinestrosa F, Rustgi V, Schwartz H, Younossi Z, Webster L, Gitlin N, Eley T, Huang SP, McPhee F, Grasela DM, Gardiner DF. Daclatasvir + asunaprevir + beclabuvir ± ribavirin for chronic HCV genotype 1-infected treatment-naive patients. Liver Int. 2016 Feb;36(2):189-97. doi: 10.1111/liv.12964. Epub 2015 Dec 6. PMID: 26473667. 14: Kao JH, Yu ML, Peng CY, Heo J, Chu CJ, Chang TT, Lee YJ, Hu TH, Yoon KT, Paik SW, Lim YS, Ahn SH, Isakov V, McPhee F, Hu W, Scott Swenson E, Yin PD, Treitel M. Daclatasvir/asunaprevir/beclabuvir, all-oral, fixed-dose combination for patients with chronic hepatitis C virus genotype 1. J Gastroenterol Hepatol. 2017 Dec;32(12):1998-2005. doi: 10.1111/jgh.13796. PMID: 28370350. 15: Teraoka Y, Uchida T, Imamura M, Hiraga N, Osawa M, Kan H, Saito Y, Tsuge M, Abe-Chayama H, Hayes CN, Makokha GN, Aikata H, Miki D, Ochi H, Ishida Y, Tateno C, Chayama K. Limitations of daclatasvir/asunaprevir plus beclabuvir treatment in cases of NS5A inhibitor treatment failure. J Gen Virol. 2018 Aug;99(8):1058-1065. doi: 10.1099/jgv.0.001091. Epub 2018 Jun 19. PMID: 29916799. 16: Zhang X. Direct anti-HCV agents. Acta Pharm Sin B. 2016 Jan;6(1):26-31. doi: 10.1016/j.apsb.2015.09.008. Epub 2015 Nov 24. PMID: 26904396; PMCID: PMC4724659. 17: Garimella T, Tao X, Sims K, Chang YT, Rana J, Myers E, Wind-Rotolo M, Bhatnagar R, Eley T, LaCreta F, AbuTarif M. Effects of a Fixed-Dose Co- Formulation of Daclatasvir, Asunaprevir, and Beclabuvir on the Pharmacokinetics of a Cocktail of Cytochrome P450 and Drug Transporter Substrates in Healthy Subjects. Drugs R D. 2018 Mar;18(1):55-65. doi: 10.1007/s40268-017-0222-8. PMID: 29255971; PMCID: PMC5833906. 18: Matsumoto J, San SN, Fujiyoshi M, Kawauchi A, Chiba N, Tagai R, Sanbe R, Yanaka S, Sakaue H, Kato Y, Nakamura H, Yamada H, Ariyoshi N. Effect of CYP3A5*3 genetic variant on the metabolism of direct-acting antivirals in vitro: a different effect on asunaprevir versus daclatasvir and beclabuvir. J Hum Genet. 2020 Jan;65(2):143-153. doi: 10.1038/s10038-019-0685-2. Epub 2019 Oct 23. PMID: 31645655. 19: Poordad F, Sievert W, Mollison L, Bennett M, Tse E, Bräu N, Levin J, Sepe T, Lee SS, Angus P, Conway B, Pol S, Boyer N, Bronowicki JP, Jacobson I, Muir AJ, Reddy KR, Tam E, Ortiz-Lasanta G, de Lédinghen V, Sulkowski M, Boparai N, McPhee F, Hughes E, Swenson ES, Yin PD; UNITY-1 Study Group. Fixed-dose combination therapy with daclatasvir, asunaprevir, and beclabuvir for noncirrhotic patients with HCV genotype 1 infection. JAMA. 2015 May 5;313(17):1728-35. doi: 10.1001/jama.2015.3860. PMID: 25942723. 20: Muir AJ, Poordad F, Lalezari J, Everson G, Dore GJ, Herring R, Sheikh A, Kwo P, Hézode C, Pockros PJ, Tran A, Yozviak J, Reau N, Ramji A, Stuart K, Thompson AJ, Vierling J, Freilich B, Cooper J, Ghesquiere W, Yang R, McPhee F, Hughes EA, Swenson ES, Yin PD. Daclatasvir in combination with asunaprevir and beclabuvir for hepatitis C virus genotype 1 infection with compensated cirrhosis. JAMA. 2015 May 5;313(17):1736-44. doi: 10.1001/jama.2015.3868. PMID: 25942724.