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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H50N6O9S.H2O
Molecular Weight 784.9212
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GRAZOPREVIR

SMILES

C=C[C@]1([H])C[C@@]1(C(=NS(=O)(=O)C2CC2)O)N=C([C@]3([H])C[C@]4([H])CN3C(=O)[C@]([H])(C(C)(C)C)N=C(O)O[C@]5([H])C[C@@]5([H])CCCCCc6c(nc7cc(ccc7n6)OC)O4)O.O

InChI

InChIKey=RXSARIJMSJWJLZ-CIAYNJNFSA-N
InChI=1S/C38H50N6O9S.H2O/c1-6-22-19-38(22,35(47)43-54(49,50)25-13-14-25)42-32(45)29-18-24-20-44(29)34(46)31(37(2,3)4)41-36(48)53-30-16-21(30)10-8-7-9-11-27-33(52-24)40-28-17-23(51-5)12-15-26(28)39-27;/h6,12,15,17,21-22,24-25,29-31H,1,7-11,13-14,16,18-20H2,2-5H3,(H,41,48)(H,42,45)(H,43,47);1H2/t21-,22-,24-,29+,30-,31-,38-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C38H50N6O9S
Molecular Weight 766.906
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Grazoprevir is a second generation NS3/4A protease inhibitor approved in the EU and the USA for the treatment of hepatitis C virus (HCV) genotypes 1 and 4 infections in adult patients in combination with elbasvir (C virus (HCV) NS5A inhibitor) as the fixed-dose combination product Zepatier with or without ribavirin. In phase III trials, 12 or 16 weeks of treatment with once-daily elbasvir/grazoprevir (fixed-dose tablet or as individual agents), taken with or without ribavirin, generally provided high rates of sustained virological response at 12 weeks (SVR12) in treatment-naive and -experienced adult patients with chronic HCV genotype 1a, 1b or 4 infection, including those with or without compensated cirrhosis, HIV co-infection, inherited blood disorders or chronic kidney disease or patients receiving opioid agonist therapy or of Japanese origin. Elbasvir/grazoprevir was generally well tolerated. Thus, elbasvir/grazoprevir, with or without ribavirin, represents an effective new option for the treatment of adults with chronic HCV genotype 1 and 4 infection, including a number of difficult-to-treat populations.

Originator

Curator's Comment:: # Merck

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZEPATIER

Approved Use

ZEPATIER is a fixed-dose combination product containing elbasvir, a hepatitis C virus (HCV) NS5A inhibitor, and grazoprevir, an HCV NS3/4A protease inhibitor, and is indicated for treatment of chronic HCV genotype 1 or 4 infection in adults. ZEPATIER is indicated for use with ribavirin in certain patient populations.

Launch Date

1.45393923E12
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Discovery of MK-5172, a Macrocyclic Hepatitis C Virus NS3/4a Protease Inhibitor.
2012 Apr 12
MK-5172, a selective inhibitor of hepatitis C virus NS3/4a protease with broad activity across genotypes and resistant variants.
2012 Aug
Grazoprevir and Elbasvir in Patients with Genotype 1 Hepatitis C Virus Infection: A Comprehensive Efficacy and Safety Analysis.
2017
Elbasvir/grazoprevir.
2017 Feb
Elbasvir/Grazoprevir (Zepatier) for Hepatitis C Virus Infection.
2017 Mar 15
Elbasvir/Grazoprevir: A Review in Chronic HCV Genotypes 1 and 4.
2017 May
Elbasvir/Grazoprevir for Patients With Hepatitis C Virus Infection and Inherited Blood Disorders: A Phase III Study.
2017 Sep
Patents

Sample Use Guides

ZEPATIER is a two-drug, fixed-dose combination product containing 50 mg of elbasvir and 100 mg of grazoprevir in a single tablet. The recommended dosage of ZEPATIER is one tablet taken orally once daily with or without food
Route of Administration: Oral
In a cell-based replicon system, MK-5172 (Grazoprevir) inhibited HCV with EC50 values of 2 nM against genotype 1a, 0.5 nM against genotype 1b, 8 nM against genotype 2a and 13 nM against genotype 3. Also, MK-5172 is effective against HCV genotypes 1a, 2a, 1b, 2b and 3a.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:44:18 UTC 2021
Edited
by admin
on Sat Jun 26 03:44:18 UTC 2021
Record UNII
4O2AB118LA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GRAZOPREVIR
DASH   USAN  
USAN  
Official Name English
GRAZOPREVIR [ORANGE BOOK]
Common Name English
GRAZOPREVIR MONOHYDRATE
WHO-DD  
Common Name English
GRAZOPREVIR MONOHYDRATE [WHO-DD]
Common Name English
GRAZOPREVIR [USAN]
Common Name English
MK-5172 MONOHYDRATE
Code English
CYCLOPROPANECARBOXAMIDE, N-((((1R,2R)-2-(5-(3-HYDROXY-6-METHOXY-2-QUINOXALINYL)PENTYL)CYCLOPROPYL)OXY)CARBONYL)-3-METHYL-L-VALYL-(4R)-4-HYDROXY-L-PROLYL-1-AMINO-N-(CYCLOPROPYLSULFONYL)-2-ETHENYL-, CYCLIC (1->2)-ETHER, HYDRATE (1:1), (1R,2S)-
Systematic Name English
GRAZOPREVIR HYDRATE [MI]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AP54
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
Code System Code Type Description
DRUG CENTRAL
5081
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
CAS
1350462-55-3
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
ChEMBL
CHEMBL2063090
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
LACTMED
Grazoprevir
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
EPA CompTox
1350462-55-3
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
WIKIPEDIA
Grazoprevir
Created by admin on Sat Jun 26 03:44:19 UTC 2021 , Edited by admin on Sat Jun 26 03:44:19 UTC 2021
PRIMARY
NCI_THESAURUS
C166768
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
FDA UNII
4O2AB118LA
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
EVMPD
SUB180368
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
RXCUI
1734630
Created by admin on Sat Jun 26 03:44:19 UTC 2021 , Edited by admin on Sat Jun 26 03:44:19 UTC 2021
PRIMARY
DRUG BANK
DB11575
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
PUBCHEM
71576667
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
MERCK INDEX
M11947
Created by admin on Sat Jun 26 03:44:18 UTC 2021 , Edited by admin on Sat Jun 26 03:44:18 UTC 2021
PRIMARY
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