Telaprevir

For research use only. Not for therapeutic Use.

  • CAT Number: A000512
  • CAS Number: 402957-28-2
  • Molecular Formula: C36H53N7O6
  • Molecular Weight: 679.90
  • Purity: ≥95%
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Telaprevir(Cat No.:A000512)is a potent, selective inhibitor of the hepatitis C virus (HCV) NS3/4A protease, an enzyme essential for viral replication. Used as part of combination therapy, it was a breakthrough in the treatment of chronic HCV genotype 1 infections, significantly improving sustained virologic response rates. Telaprevir works by blocking the cleavage of viral polyproteins, thereby halting viral replication. While its use has been largely replaced by newer therapies with improved safety profiles, Telaprevir remains a milestone in the development of direct-acting antivirals for HCV management.


Catalog Number A000512
CAS Number 402957-28-2
Synonyms

LY-570310, MP-424; 402957-28-2; VX-950; Incivek; Incivo; VX 950

Molecular Formula C36H53N7O6
Purity ≥95%
Target Metabolic Enzyme/Protease
Solubility >33mg/mL in DMSO
Storage -20°C
IUPAC Name (3S,3aS,6aR)-2-[(2S)-2-[[(2S)-2-cyclohexyl-2-(pyrazine-2-carbonylamino)acetyl]amino]-3,3-dimethylbutanoyl]-N-[(3S)-1-(cyclopropylamino)-1,2-dioxohexan-3-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrole-3-carboxamide
InChI InChI=1S/C36H53N7O6/c1-5-10-25(29(44)34(48)39-23-15-16-23)40-33(47)28-24-14-9-13-22(24)20-43(28)35(49)30(36(2,3)4)42-32(46)27(21-11-7-6-8-12-21)41-31(45)26-19-37-17-18-38-26/h17-19,21-25,27-28,30H,5-16,20H2,1-4H3,(H,39,48)(H,40,47)(H,41,45)(H,42,46)/t22-,24-,25-,27-,28-,30+/m0/s1
InChIKey BBAWEDCPNXPBQM-GDEBMMAJSA-N
SMILES CCC[C@@H](C(=O)C(=O)NC1CC1)NC(=O)[C@@H]2[C@H]3CCC[C@H]3CN2C(=O)[C@H](C(C)(C)C)NC(=O)[C@H](C4CCCCC4)NC(=O)C5=NC=CN=C5
Reference

1: Sacchi A, Tumino N, Turchi F, Refolo G, Fimia G, Ciccosanti F, Montalbano M,
Lionetti R, Taibi C, D/’Offizi G, Casetti R, Bordoni V, Cimini E, Martini F,
Agrati C. Dendritic cells activation is associated with sustained virological
response to telaprevir treatment of HCV-infected patients. Clin Immunol. 2017
Oct;183:82-90. doi: 10.1016/j.clim.2017.07.017. Epub 2017 Jul 20. PubMed PMID:
28736275.
<br>

2: Akutagawa M, Ide K, Kawasaki Y, Yamanaka M, Iketani R, Yamada H, Masaki N.
Safety Profile of Telaprevir-Based Triple Therapy in Elderly Patients: A
Real-World Retrospective Cohort Study. Biol Pharm Bull. 2017 Sep
1;40(9):1525-1529. doi: 10.1248/bpb.b17-00354. Epub 2017 Jun 9. PubMed PMID:
28603159.
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3: Cuypers L, Libin P, Schrooten Y, Theys K, Di Maio VC, Cento V, Lunar MM,
Nevens F, Poljak M, Ceccherini-Silberstein F, Nowé A, Van Laethem K, Vandamme AM.
Exploring resistance pathways for first-generation NS3/4A protease inhibitors
boceprevir and telaprevir using Bayesian network learning. Infect Genet Evol.
2017 Sep;53:15-23. doi: 10.1016/j.meegid.2017.05.007. Epub 2017 May 9. PubMed
PMID: 28499845.
<br>

4: Kumada H, Mochida S, Nakamuta M, Suzuki F, Yagi T, Takasaki R, Okai M, Kamiya
N, Okada Y, Hirota S, Orihashi M, Ochi M, Chayama K. Efficacy and safety of
telaprevir with natural human interferon-β and ribavirin in Japanese chronic
hepatitis C patients with depression. Hepatol Res. 2017 May 11. doi:
10.1111/hepr.12914. [Epub ahead of print] PubMed PMID: 28497489.
<br>

5: Bichoupan K, Tandon N, Martel-Laferriere V, Patel NM, Sachs D, Ng M, Schonfeld
EA, Pappas A, Crismale J, Stivala A, Khaitova V, Gardenier D, Linderman M, Olson
W, Perumalswami PV, Schiano TD, Odin JA, Liu LU, Dieterich DT, Branch AD. Factors
associated with success of telaprevir- and boceprevir-based triple therapy for
hepatitis C virus infection. World J Hepatol. 2017 Apr 18;9(11):551-561. doi:
10.4254/wjh.v9.i11.551. PubMed PMID: 28469811; PubMed Central PMCID: PMC5395804.
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6: Mangia A, Foster GR, Berg CP, Curescu M, Ledinghen V, Habersetzer F,
Manolakopoulos S, Negri E, Papatheodoridis G, Ahlers S, Castillo M, Bakalos G,
Mauss S; PegBase Group Investigators. Efficacy and safety profile of boceprevir-
or telaprevir-based triple therapy or dual peginterferon alfa-2a or alfa-2b plus
ribavirin therapy in chronic hepatitis C: the real-world PegBase observational
study. Ann Gastroenterol. 2017;30(3):327-343. doi: 10.20524/aog.2017.0136. Epub
2017 Mar 23. PubMed PMID: 28469364; PubMed Central PMCID: PMC5411384.
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7: Yamagiwa S, Ishikawa T, Waguri N, Sugitani S, Wakabayashi H, Ohkoshi S,
Tsukishiro T, Takahashi T, Watanabe T, Terai S. Efficacy and safety of
telaprevir- and simeprevir-based triple therapies for older patients with chronic
hepatitis C. World J Hepatol. 2017 Feb 18;9(5):252-262. doi:
10.4254/wjh.v9.i5.252. PubMed PMID: 28261382; PubMed Central PMCID: PMC5316845.
<br>

8: Boesecke C, Singh GKJ, Scholten SH, Lutz T, Baumgarten A, Schneeweiss SM,
Trein A, Rausch M, Ingiliz P, Rockstroh JK, Nelson M; CHAT study group.
Telaprevir-containing triple therapy in acute HCV coinfection: The CHAT Study.
Antivir Ther. 2017 Feb 27. doi: 10.3851/IMP3143. [Epub ahead of print] PubMed
PMID: 28240597.
<br>

9: Ide K, Kawasaki Y, Iketani R, Masaki N. Risk Factors for Treatment
Discontinuation Caused by Adverse Events When Using Telaprevir, Peginterferon,
and Ribavirin to Treat Chronic Hepatitis C: A Real-World Retrospective Cohort
Study. Biol Pharm Bull. 2017 May 1;40(5):645-649. doi: 10.1248/bpb.b16-00941.
Epub 2017 Feb 17. PubMed PMID: 28216512.
<br>

10: Iketani R, Ide K, Yamada H, Kawasaki Y, Masaki N. The Safety Profile of
Telaprevir-Based Triple Therapy in Clinical Practice: A Retrospective Cohort
Study. Biol Pharm Bull. 2017 May 1;40(5):687-692. doi: 10.1248/bpb.b16-00989.
Epub 2017 Feb 9. PubMed PMID: 28179602.

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