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Beclabuvir

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Chemical compound

Pharmaceutical compound

Beclabuvir
Clinical data

Other names	BMS-791325
Legal status
Legal status	US: Investigational New Drug
Identifiers
IUPAC name (1aR,12bS)-8-Cyclohexyl-N-(dimethylsulfamoyl)-11-methoxy-1a-{[(1R,5S)-3-methyl-3,8-diazabicyclo[3.2.1]oct-8-yl]carbonyl}-1,1a,2,12b-tetrahydrocyclopropa[d]indolo[2,1-a] [2]benzazepine-5-carboxamide
CAS Number	958002-33-0
PubChemCID	56934415
ChemSpider	27289076
UNII	MYW1X5CO9S
KEGG	D10610^Y
CompTox Dashboard(EPA)	DTXSID701026084
Chemical and physical data
Formula	C₃₆H₄₅N₅O₅S
Molar mass	659.85 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1C[C@H]2CC[C@@H](C1)N2C(=O)[C@]34C[C@H]3c5cc(ccc5-c6c(c7ccc(cc7n6C4)C(=O)NS(=O)(=O)N(C)C)C8CCCCC8)OC
InChI 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 Key:ZTTKEBYSXUCBSE-QDFUAKMASA-N

Beclabuvir (also known by the research nameBMS-791325; abbreviatedBCV) is anantiviral drug for the treatment ofhepatitis C virus (HCV) infection that has been studied inclinical trials. In February 2017,Bristol-Myers Squibb began sponsoring a post-marketing trial of beclabuvir, in combination withasunaprevir anddaclatasvir, to study the combination's safety profile with regard to liver function.^[1] From February 2014 to November 2016, aphase II clinical trial was conducted on the combination of asunaprevir/daclatasvir/beclabuvir (beclabuvir is referred to as BMS-791325 in the trial) on patients infected with bothHIV and HCV.^[2] Furthermore, a recent meta-analysis of six published six clinical trials showed high response rates in HCV genotype 1-infected patients treated withdaclatasvir,asunaprevir, and beclabuvir irrespective ofribavirin use, priorinterferon-based therapy, or restriction onnoncirrhotic patients,IL28B genotype, or baseline resistance-associated variants^[3]

Pharmacology

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Beclabuvir acts as aNS5B (RNA polymerase) inhibitor.^[4]

References

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^Clinical trial numberNCT03071133 for "Asunaprevir/Daclatasvir/Beclabuvir Fixed-Dose Combination Safety Surveillance in Japanese Patients With Chronic Hepatitis C (HCV) or Japanese Patients With Compensated Cirrhosis" atClinicalTrials.gov
^Clinical trial numberNCT02124044 for "Safety, Tolerability, and Efficacy of Asunaprevir and Daclatasvir in Subjects Coinfected With HIV-HCV" atClinicalTrials.gov
^Ahmed AM, Doheim MF, Mattar OM, Sherif NA, Truong DH, Hoa PT, et al. (May 2018). "Beclabuvir in combination with asunaprevir and daclatasvir for hepatitis C virus genotype 1 infection: A systematic review and meta-analysis".Journal of Medical Virology.90 (5):907–918.doi:10.1002/jmv.24947.PMID 28892235.S2CID 3829214.
^Tatum H, Thuluvath PJ, Lawitz E, Martorell C, DeMicco M, Cohen S, et al. (August 2015)."A randomized, placebo-controlled study of the NS5B inhibitor beclabuvir with peginterferon/ribavirin for HCV genotype 1".Journal of Viral Hepatitis.22 (8):658–64.doi:10.1111/jvh.12372.PMID 25496007.

RNA virus antivirals (primarilyJ05, alsoS01AD andD06BB)

Hepatitis C

NS3/4A protease inhibitors (–previr)	Asunaprevir Boceprevir^‡ Ciluprevir^§ Danoprevir^† Faldaprevir^‡ Glecaprevir Grazoprevir Narlaprevir Paritaprevir Simeprevir Sovaprevir^† Telaprevir^‡ Vaniprevir Vedroprevir^§ Voxilaprevir
NS5A inhibitors (–asvir)	Coblopasvir Daclatasvir^# Elbasvir Ledipasvir Odalasvir^† Ombitasvir Pibrentasvir Ravidasvir^† Ruzasvir^† Samatasvir^† Velpatasvir
NS5B RNA polymerase inhibitors (–buvir)	Beclabuvir^† Bemnifosbuvir^† Dasabuvir^# Deleobuvir^§ Filibuvir^§ GS-6620^§ IDX-184^§ Setrobuvir^§ Sofosbuvir^# Tegobuvir^§ TMC-647055^§ Radalbuvir^† Uprifosbuvir^†
Combination drugs	Elbasvir/grazoprevir Glecaprevir/pibrentasvir Ledipasvir/sofosbuvir^# Ombitasvir/paritaprevir/ritonavir^# Sofosbuvir/daclatasvir Sofosbuvir/velpatasvir^# Sofosbuvir/velpatasvir/voxilaprevir

Hepatitis D

Bulevirtide

Picornavirus

viral entry:Pleconaril^†

Anti-influenza agents

neuraminidase inhibitors/release phase (Oseltamivir^#
Zanamivir
Peramivir,Laninamivir^†)

Multiple/general

Interferon	Interferon alfa 2b Peginterferon alfa-2a^# Peginterferon alfa-2b^#
3CL protease inhibitors (–trelvir)	Atilotrelvir Ensitrelvir^† Ibuzatrelvir Leritrelvir Lufotrelvir Nirmatrelvir^† (+ritonavir)^† Rupintrivir Simnotrelvir (+ritonavir^†)
RNA pol inhibitors	CMX521^§ Deuremidevir^† Favipiravir Galidesivir^† GS-441524^§ Remdesivir MK-608^§ Mericitabine^† Molnupiravir NITD008^§ Ribavirin^# Taribavirin^† Triazavirin Valopicitabine^†
Multiple/Unknown/Other	EICAR^§ Merimepodib^§ Moroxydine Presatovir^†

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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