Boceprevir
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MedKoo CAT#: 300235

CAS#: 394730-60-0

Description: Boceprevir (INN, trade name Victrelis) is a protease inhibitor used as a treatment for hepatitis C genotype 1. It binds to HCV nonstructural 3 NS3 (HCV) active site. It was being developed by Schering-Plough, but is now being developed by Merck since Schering was acquired in 2009. It was approved by the FDA on May 13, 2011.


Chemical Structure

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Boceprevir
CAS# 394730-60-0

Theoretical Analysis

MedKoo Cat#: 300235
Name: Boceprevir
CAS#: 394730-60-0
Chemical Formula: C27H45N5O5
Exact Mass: 519.34207
Molecular Weight: 519.68
Elemental Analysis: C, 62.40; H, 8.73; N, 13.48; O, 15.39

Price and Availability

Size Price Availability Quantity
50.0mg USD 150.0 Ready to ship
100.0mg USD 250.0 Ready to ship
200.0mg USD 450.0 Ready to ship
500.0mg USD 550.0 Ready to ship
1.0g USD 750.0 Ready to ship
2.0g USD 950.0 Ready to ship
5.0g USD 1650.0 Ready to ship
10.0g USD 2650.0 Ready to ship
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Synonym: EBP 520; EBP520; EBP-520; SCH503034; SCH-503034; SCH 503034; Boceprevir; trade name: Victrelis.

IUPAC/Chemical Name: (1R,2S,5S)-N-(4-amino-1-cyclobutyl-3,4-dioxobutan-2-yl)-3-((S)-2-(3-(tert-butyl)ureido)-3,3-dimethylbutanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide

InChi Key: LHHCSNFAOIFYRV-DOVBMPENSA-N

InChi Code: InChI=1S/C27H45N5O5/c1-25(2,3)20(30-24(37)31-26(4,5)6)23(36)32-13-15-17(27(15,7)8)18(32)22(35)29-16(19(33)21(28)34)12-14-10-9-11-14/h14-18,20H,9-13H2,1-8H3,(H2,28,34)(H,29,35)(H2,30,31,37)/t15-,16?,17-,18-,20+/m0/s1

SMILES Code: O=C([C@@H]1[C@@]2([H])C(C)(C)[C@@]2([H])CN1C([C@@H](NC(NC(C)(C)C)=O)C(C)(C)C)=O)NC(C(C(N)=O)=O)CC3CCC3

Appearance: Off-white to pale yellow 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 (16mg/mL), ethanol (25mg/mL); DMF (25mg/mL).

Shelf Life: >2 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

Biological target: Boceprevir is a HCV NS3 protease inhibitor with a Ki of 14 nM in both enzyme assay and an EC90 of 350 nM in cell-based replicon assay.
In vitro activity: The antiviral efficacy in vitro against CDV (canine distemper virus) of boceprevir was evaluated. CDV growth in VERO cells was inhibited by boceprevir at non-cytotoxic concentrations, as evaluated by end-point viral titration in cell monolayers and by quantification of viral RNA using quantitative RT-PCR. By quantitative RT-PCR, a significant reduction of viral growth was observed in cells treated with boceprevir. Boceprevir was able to decrease CDV growth by up to 3.4458 logs with respect to untreated infected cells at the highest virus dilutions. Reference: J Virol Methods. 2017 Oct;248:207-211. https://www.sciencedirect.com/science/article/abs/pii/S0166093417303713?via%3Dihub
In vivo activity: TBD

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 44.22 85.09
DMF 25.0 48.11
Ethanol 25.0 48.11
Ethanol:PBS (pH 7.2) (1:6) 0.14 0.27

Preparing Stock Solutions

The following data is based on the product molecular weight 519.68 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. Lanave G, Cavalli A, Martella V, Fontana T, Losappio R, Tempesta M, Decaro N, Buonavoglia D, Camero M. Ribavirin and boceprevir are able to reduce Canine distemper virus growth in vitro. J Virol Methods. 2017 Oct;248:207-211. doi: 10.1016/j.jviromet.2017.07.012. Epub 2017 Jul 29. PMID: 28760649. 2. Fu L, Ye F, Feng Y, Yu F, Wang Q, Wu Y, Zhao C, Sun H, Huang B, Niu P, Song H, Shi Y, Li X, Tan W, Qi J, Gao GF. Both Boceprevir and GC376 efficaciously inhibit SARS-CoV-2 by targeting its main protease. Nat Commun. 2020 Sep 4;11(1):4417. doi: 10.1038/s41467-020-18233-x. PMID: 32887884; PMCID: PMC7474075.
In vitro protocol: 1. Lanave G, Cavalli A, Martella V, Fontana T, Losappio R, Tempesta M, Decaro N, Buonavoglia D, Camero M. Ribavirin and boceprevir are able to reduce Canine distemper virus growth in vitro. J Virol Methods. 2017 Oct;248:207-211. doi: 10.1016/j.jviromet.2017.07.012. Epub 2017 Jul 29. PMID: 28760649. 2. Fu L, Ye F, Feng Y, Yu F, Wang Q, Wu Y, Zhao C, Sun H, Huang B, Niu P, Song H, Shi Y, Li X, Tan W, Qi J, Gao GF. Both Boceprevir and GC376 efficaciously inhibit SARS-CoV-2 by targeting its main protease. Nat Commun. 2020 Sep 4;11(1):4417. doi: 10.1038/s41467-020-18233-x. PMID: 32887884; PMCID: PMC7474075.
In vivo protocol: TBD

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1: Esteban R, Buti M. Triple therapy with boceprevir or telaprevir for treatment naïve HCV patients. Best Pract Res Clin Gastroenterol. 2012 Aug;26(4):445-53. doi: 10.1016/j.bpg.2012.09.001. Review. PubMed PMID: 23199503.

2: [Boceprevir (Victrelis), oral administration]. J Pharm Belg. 2012 Jun;(2):37-9. Review. French. PubMed PMID: 22978014.

3: Chang MH, Gordon LA, Fung HB. Boceprevir: a protease inhibitor for the treatment of hepatitis C. Clin Ther. 2012 Oct;34(10):2021-38. doi: 10.1016/j.clinthera.2012.08.009. Epub 2012 Sep 11. Review. PubMed PMID: 22975763.

4: Venkatraman S. Discovery of boceprevir, a direct-acting NS3/4A protease inhibitor for treatment of chronic hepatitis C infections. Trends Pharmacol Sci. 2012 May;33(5):289-94. doi: 10.1016/j.tips.2012.03.012. Epub 2012 Apr 19. Review. PubMed PMID: 22521415.

5: Jacobson IM, Pawlotsky JM, Afdhal NH, Dusheiko GM, Forns X, Jensen DM, Poordad F, Schulz J. A practical guide for the use of boceprevir and telaprevir for the treatment of hepatitis C. J Viral Hepat. 2012 May;19 Suppl 2:1-26. doi: 10.1111/j.1365-2893.2012.01590.x. Review. PubMed PMID: 22404758.

6: Wilby KJ, Partovi N, Ford JA, Greanya E, Yoshida EM. Review of boceprevir and telaprevir for the treatment of chronic hepatitis C. Can J Gastroenterol. 2012 Apr;26(4):205-10. Review. PubMed PMID: 22506260; PubMed Central PMCID: PMC3354889.

7: Trembling PM, Tanwar S, Dusheiko GM. Boceprevir: an oral protease inhibitor for the treatment of chronic HCV infection. Expert Rev Anti Infect Ther. 2012 Mar;10(3):269-79. doi: 10.1586/eri.12.8. Review. PubMed PMID: 22397560.

8: Klibanov OM, Vickery SB, Olin JL, Smith LS, Williams SH. Boceprevir: a novel NS3/4 protease inhibitor for the treatment of hepatitis C. Pharmacotherapy. 2012 Feb;32(2):173-90. doi: 10.1002/PHAR.1046. Review. PubMed PMID: 22392426.

9: Swiss Association for the Study of the Liver. Treatment of chronic hepatitis C genotype 1 with triple therapy comprising telaprevir or boceprevir. Swiss Med Wkly. 2012 Feb 24;142:w13516. doi: 10.4414/smw.2012.13516. Review. PubMed PMID: 22367957.

10: Wilby KJ, Greanya ED, Ford JA, Yoshida EM, Partovi N. A review of drug interactions with boceprevir and telaprevir: implications for HIV and transplant patients. Ann Hepatol. 2012 Mar-Apr;11(2):179-85. Review. PubMed PMID: 22345334.



Additional Information

Boceprevir is manufactured as an approximately equal mixture of two diastereomers. Boceprevir is a white to off-white amorphous powder. It is freely soluble in methanol, ethanol and isopropanol and slightly soluble in water.