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Details

Stereochemistry ABSOLUTE
Molecular Formula C49H55N9O7
Molecular Weight 882.019
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELBASVIR

SMILES

CC(C)[C@@]([H])(C(=O)N1CCC[C@@]1([H])c2ncc(-c3ccc4c(c3)cc5-c6ccc(cc6O[C@@]([H])(c7ccccc7)n45)-c8cnc([C@]9([H])CCCN9C(=O)[C@]([H])(C(C)C)N=C(O)OC)[nH]8)[nH]2)N=C(O)OC

InChI

InChIKey=BVAZQCUMNICBAQ-PZHYSIFUSA-N
InChI=1S/C49H55N9O7/c1-27(2)41(54-48(61)63-5)45(59)56-20-10-14-37(56)43-50-25-34(52-43)30-17-19-36-32(22-30)23-39-33-18-16-31(24-40(33)65-47(58(36)39)29-12-8-7-9-13-29)35-26-51-44(53-35)38-15-11-21-57(38)46(60)42(28(3)4)55-49(62)64-6/h7-9,12-13,16-19,22-28,37-38,41-42,47H,10-11,14-15,20-21H2,1-6H3,(H,50,52)(H,51,53)(H,54,61)(H,55,62)/t37-,38-,41-,42-,47-/m0/s1

HIDE SMILES / InChI
Elbasvir is an inhibitor of the Hepatitis C Virus (HCV) Non-Structural protein 5A (NS5A). Elbasvir was approved by the FDA in January 2016 for the treatment of hepatitis C. It was developed by Merck and completed Phase III trials, used in combination with the NS3/4A protease inhibitor grazoprevir under the trade name Zepatier. Zepatier is indicated for treatment of chronic HCV genotype 1 or 4 infection in adults.

Originator

Curator's Comment:: # Merck & Co

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.0 pM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZEPATIER

Approved Use

ZEPATIER® is indicated for the treatment of chronic hepatitis C virus (HCV) genotype 1 or 4 infection in adults.

Launch Date

1.45393923E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
198 nM
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
ELBASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2710.5 nM × h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
ELBASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.5 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
ELBASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
24 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
ELBASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
ELBASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg 1 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 1 times / day
Route: oral
Route: multiple
Dose: 100 mg, 1 times / day
Sources:
unhealthy, 34.6 years
n = 5
Health Status: unhealthy
Condition: HCV GT3 infection
Age Group: 34.6 years
Sex: M
Population Size: 5
Sources:
PubMed

PubMed

TitleDatePubMed
Grazoprevir + elbasvir for the treatment of hepatitis C virus infection.
2016
The Combination of Grazoprevir, a Hepatitis C Virus (HCV) NS3/4A Protease Inhibitor, and Elbasvir, an HCV NS5A Inhibitor, Demonstrates a High Genetic Barrier to Resistance in HCV Genotype 1a Replicons.
2016 May
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. ZEPATIER is used in combination with ribavirin in certain patient populations
Route of Administration: Oral
Elbasvir was highly potent in GT1a wild-type replicon cells, with 90% effective concentration (EC90) value of 0.006 nM.
Name Type Language
ELBASVIR
DASH   INN   USAN   WHO-DD  
INN   USAN  
Official Name English
ELBASVIR COMPONENT OF ZEPATIER
Common Name English
ZEPATIER COMPONENT OF ELBASVIR
Common Name English
ELBASVIR [JAN]
Common Name English
ELBASVIR [MI]
Common Name English
ELBASVIR [ORANGE BOOK]
Common Name English
ELBASVIR [WHO-DD]
Common Name English
CARBAMIC ACID, N,N'-(((6S)-6-PHENYL-6H-INDOLO(1,2-C)(1,3)BENZOXAZINE-3,10-DIYL)BIS(1H-IMIDAZOLE-5,2-DIYL-(2S)-2,1-PYRROLIDINEDIYL((1S)-1-(1-METHYLETHYL)-2-OXO-2,1-ETHANEDIYL)))BIS-, C,C'-DIMETHYL ESTER
Common Name English
MK-8742
Code English
ELBASVIR [INN]
Common Name English
ELBASVIR [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000191256
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
WHO-ATC J05AP54
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C166892
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
WIKIPEDIA
ELBASVIR
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
RXCUI
1734628
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
EPA CompTox
1370468-36-2
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
LACTMED
Elbasvir
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
CAS
1370468-36-2
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
DRUG CENTRAL
5080
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
INN
9851
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
EVMPD
SUB174125
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
MERCK INDEX
M11946
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
ChEMBL
CHEMBL3039514
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
FDA UNII
632L571YDK
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
NDF-RT
N0000190113
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
DRUG BANK
DB11574
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY
PUBCHEM
71661251
Created by admin on Sat Jun 26 15:20:59 UTC 2021 , Edited by admin on Sat Jun 26 15:20:59 UTC 2021
PRIMARY