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Details

Stereochemistry ACHIRAL
Molecular Formula C22H23FN2O5S
Molecular Weight 446.492
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NESBUVIR

SMILES

CNC(=O)C1=C(OC2=CC(N(CCO)S(C)(=O)=O)=C(C=C12)C3CC3)C4=CC=C(F)C=C4

InChI

InChIKey=WTDWVLJJJOTABN-UHFFFAOYSA-N
InChI=1S/C22H23FN2O5S/c1-24-22(27)20-17-11-16(13-3-4-13)18(25(9-10-26)31(2,28)29)12-19(17)30-21(20)14-5-7-15(23)8-6-14/h5-8,11-13,26H,3-4,9-10H2,1-2H3,(H,24,27)

HIDE SMILES / InChI
Molecular Formula C22H23FN2O5S
Molecular Weight 446.492
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Nesbuvir (previously known as VB-19796 and HCV-796) is an inhibitor of hepatitis C NS5B RNA-dependent RNA polymerase. The drug was tested in phase II in patients with hepatitis C in combination with rebetol and peg-intron, however, its development was terminated due to safety issues.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.081 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
2052
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
2546
 no
CYP2C9
2497
 yes [IC50 10.684 uM]
CYP3A4
2633
 yes [IC50 13.4504 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
P-gp
2052
 no
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00FCH9
https://www.1pchem.com/search?query=1P00FCH9
ApexBio Technology
A3655
https://www.apexbt.com/catalogsearch/result/?q=A3655
BOC Sciences
691852-58-1
http://www.bocsci.com/description.asp?cas=691852-58-1
Chem Scene
CS-0689
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0689
ChemShuttle
157192
https://www.chemshuttle.com/catalogsearch/result/?q=157192
Debye Scientific
DA-33585
https://www.debyesci.com/index.php?id=product&ext[cno]=DA-33585
eMolecules
44811504
https://orderbb.emolecules.com/search/#?query=44811504
eNovation Chemicals
D501874
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D501874&searchbtn.x=0&searchbtn.y=0
Excenen
EX-A2110
http://www.excenen.com/searchresultlist.php?id=EX-A2110
mcule
MCULE-6575655722
https://mcule.com/MCULE-6575655722/
MedChem Express
HY-14775
https://www.medchemexpress.com/search.html?q=HY-14775&ft=&fa=&fp=
MolPort
MolPort-023-293-555
https://www.molport.com/shop/molecule-link/MolPort-023-293-555
ShangHai Biochempartner
BCP14777
http://www.biochempartner.com/search_BCP14777
PubMed

PubMed

TitleDatePubMed
In vitro efficacy of approved and experimental antivirals against novel genotype 3 hepatitis C virus subgenomic replicons.
2013-11
In vitro characterization of GSK2485852, a novel hepatitis C virus polymerase inhibitor.
2013-11
Restoration of the activated Rig-I pathway in hepatitis C virus (HCV) replicon cells by HCV protease, polymerase, and NS5A inhibitors in vitro at clinically relevant concentrations.
2013-09
MK-5172, a selective inhibitor of hepatitis C virus NS3/4a protease with broad activity across genotypes and resistant variants.
2012-08
Discovery of substituted N-phenylbenzenesulphonamides as a novel class of non-nucleoside hepatitis C virus polymerase inhibitors.
2012-08
Cellular growth kinetics distinguish a cyclophilin inhibitor from an HSP90 inhibitor as a selective inhibitor of hepatitis C virus.
2012
The hepatitis C virus (HCV) NS4B RNA binding inhibitor clemizole is highly synergistic with HCV protease inhibitors.
2010-07-01
Mechanisms of activity and inhibition of the hepatitis C virus RNA-dependent RNA polymerase.
2010-04-30
Inhibitors of hepatitis C virus polymerase: synthesis and characterization of novel 2-oxy-6-fluoro-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-benzamides.
2010-04-01
Substituted imidazopyridines as potent inhibitors of HCV replication.
2009-05
Severe hepatocellular injury with apoptosis induced by a hepatitis C polymerase inhibitor.
2009-04
HCV796: A selective nonstructural protein 5B polymerase inhibitor with potent anti-hepatitis C virus activity in vitro, in mice with chimeric human livers, and in humans infected with hepatitis C virus.
2009-03
Molecular mechanism of hepatitis C virus replicon variants with reduced susceptibility to a benzofuran inhibitor, HCV-796.
2008-09
Existence of hepatitis C virus NS5B variants naturally resistant to non-nucleoside, but not to nucleoside, polymerase inhibitors among untreated patients.
2008-06
The hepatitis C virus replicon presents a higher barrier to resistance to nucleoside analogs than to nonnucleoside polymerase or protease inhibitors.
2008-05
Patents

Patents

20040162318
1
JP2006510736A
2
JP4537315B2
1

Sample Use Guides

In Vivo Use Guide
Nesbuvir is administered at a dose of 500 mg, every 12 hours for 48 weeks (in combination with rebetol and peg-intron).
Route of Administration: Oral
In Vitro Use Guide
Cells bearing a genotype 1b HCV replicon were treated multiple times with 0.1 and 1 uM nesbuvir. At the end of the 16-day treatment, about 3.6 log10 and 4.2 log10 reductions of HCV RNA levels were observed, respectively. The concentration of the compound that inhibited 50% of the HCV RNA level was 9 nM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:31:15 GMT 2025
Edited
by admin
on Mon Mar 31 18:31:15 GMT 2025
Record UNII
EYK815W3Z8
Record Status Validated (UNII)
Record Version
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Name Type Language
NESBUVIR
INN   USAN  
INN   USAN  
Official Name English
HCV796
Preferred Name English
NESBUVIR [USAN]
Common Name English
3-BENZOFURANCARBOXAMIDE, 5-CYCLOPROPYL-2-(4-FLUOROPHENYL)-6-((2-HYDROXYETHYL)(METHYLSULFONYL)AMINO)-N-METHYL-
Systematic Name English
HCV-796
Code English
5-Cyclopropyl-2-(4-fluorophenyl)-6-[(2-hydroxyethyl)(methylsulfonyl)amino]-N-methyl-1-benzofuran-3-carboxamide
Systematic Name English
Nesbuvir [WHO-DD]
Common Name English
nesbuvir [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
NCI_THESAURUS C25995
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
Code System Code Type Description
INN
8961
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
PUBCHEM
11561383
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
CAS
691852-58-1
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
FDA UNII
EYK815W3Z8
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
NCI_THESAURUS
C76498
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
EVMPD
SUB35634
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL1092581
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
USAN
TT-60
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
MESH
C539481
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
DRUG BANK
DB07238
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID90219225
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
SMS_ID
100000128527
Created by admin on Mon Mar 31 18:31:15 GMT 2025 , Edited by admin on Mon Mar 31 18:31:15 GMT 2025
PRIMARY
Related Record Type Details
HEPATITIS C VIRUS
TARGET ORGANISM->INHIBITOR
HCV NS5B POLYMERASE
TARGET -> INHIBITOR
Related Record Type Details
Structure of NESBUVIR
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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