boceprevir   Click here for help

GtoPdb Ligand ID: 7876

Synonyms: EBP-520 | EBP520 | SCH-503034 | SCH503034 | Victrelis®
Approved drug
boceprevir is an approved drug (EMA & FDA (2011))
Compound class: Synthetic organic
Comment: Boceprevir is an active site-binding inhibitor of the main protease (nonstructural protein 3, NS3) of hepatitis C virus (HCV). A patent claims boceprevir for repurposing as a cathepsin A modulator [4]. More recently it has been reported to inhibit the 3CL protease (Mpro) of several coronaviruses, including SARS-CoV-2 Mpro [1-2]. An alternative enantiomer is reported in the SARS-CoV-2 Mpro/boceprevir crystal structure 6WNP, which maps to PubChem CID 71316139.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 14
Topological polar surface area 150.7
Molecular weight 519.34
XLogP 2.83
No. Lipinski's rules broken 0
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Canonical SMILES O=C(NC(C)(C)C)NC(C(C)(C)C)C(=O)N1CC2C(C1C(=O)NC(C(=O)C(=O)N)CC1CCC1)C2(C)C
Isomeric SMILES O=C(NC(C)(C)C)N[C@@H](C(C)(C)C)C(=O)N1C[C@H]2[C@@H]([C@H]1C(=O)NC(C(=O)C(=O)N)CC1CCC1)C2(C)C
InChI 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
1. Anson BJ, Chapman ME, Lendy EK, Pshenychnyi S, D’Aquila RT, Satchell KJF, Mesecar AD. (2020)
Broad-spectrum inhibition of coronavirus main and papain-like proteases by HCV drugs.
Nature Research, PrePrint, Under Review. DOI: 10.21203/
2. Baker JD, Uhrich RL, Kraemer GC, Love JE, Kraemer BC. (2021)
A drug repurposing screen identifies hepatitis C antivirals as inhibitors of the SARS-CoV2 main protease.
PLoS One, 16 (2): e0245962. [PMID:33524017]
3. Ma C, Sacco MD, Hurst B, Townsend JA, Hu Y, Szeto T, Zhang X, Tarbet B, Marty MT, Chen Y et al.. (2020)
Boceprevir, GC-376, and calpain inhibitors II, XII inhibit SARS-CoV-2 viral replication by targeting the viral main protease.
Cell Res, 30 (8): 678-692. DOI: 10.1038/s41422-020-0356-z [PMID:32541865]
4. Ruf S et al.. (2013)
Use of boceprevir and related compounds in atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases.
Patent number: WO2013072327. Assignee: Sanofi. Priority date: 14/11/2011. Publication date: 23/05/2013.