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Details

Stereochemistry ABSOLUTE
Molecular Formula C49H55N9O7
Molecular Weight 882.0171
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELBASVIR

SMILES

[H][C@]1(CCCN1C(=O)[C@@H](NC(=O)OC)C(C)C)C2=NC=C(N2)C3=CC4=C(C=C3)N5[C@@H](OC6=C(C=CC(=C6)C7=CN=C(N7)[C@]8([H])CCCN8C(=O)[C@@H](NC(=O)OC)C(C)C)C5=C4)C9=CC=CC=C9

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
Molecular Formula C49H55N9O7
Molecular Weight 882.0171
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Merck
216
Curator's Comment: # Merck & Co

Approval Year

2016
495
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 5.0 pM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
ZEPATIER

Approved Use

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

Launch Date

2016
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
198 nM
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29724498
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
GRAZOPREVIR
 ELBASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2710.5 nM × h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29724498
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
GRAZOPREVIR
 ELBASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
16.5 h
EXPERIMENT
https://www.ncbi.nlm.nih.gov/pubmed/29724498
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
GRAZOPREVIR
 ELBASVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
24 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208261s002lbl.pdf
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
GRAZOPREVIR
 ELBASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208261s002lbl.pdf
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered: GRAZOPREVIR
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:
https://pubmed.ncbi.nlm.nih.gov/29703432
unhealthy, 34.6 years
n = 5
Health Status: unhealthy
Condition: HCV GT3 infection
Age Group: 34.6 years
Sex: M
Population Size: 5
Sources:
https://pubmed.ncbi.nlm.nih.gov/29703432
Sources:
https://pubmed.ncbi.nlm.nih.gov/29703432
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:132967
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:132967
MolPort
MolPort-046-069-318
https://www.molport.com/shop/molecule-link/MolPort-046-069-318
ZINC
ZINC000150588351
http://zinc15.docking.org/substances/ZINC000150588351
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

Patents

208261-001
1
WO2016105670A1
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Elbasvir was highly potent in GT1a wild-type replicon cells, with 90% effective concentration (EC90) value of 0.006 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:51:31 GMT 2023
Edited
by admin
on Sat Dec 16 02:51:31 GMT 2023
Record UNII
632L571YDK
Record Status Validated (UNII)
Record Version
  • Download
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
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
Elbasvir [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000191256
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
WHO-ATC J05AP54
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C166892
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
WIKIPEDIA
ELBASVIR
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
RXCUI
1734628
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
DAILYMED
632L571YDK
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
USAN
AB-60
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
LACTMED
Elbasvir
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
CHEBI
132967
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
CAS
1370468-36-2
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
DRUG CENTRAL
5080
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
INN
9851
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
EPA CompTox
DTXSID10160043
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
EVMPD
SUB174125
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
MERCK INDEX
m11946
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
ChEMBL
CHEMBL3039514
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
FDA UNII
632L571YDK
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
SMS_ID
100000160902
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
NDF-RT
N0000190113
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
DRUG BANK
DB11574
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
PUBCHEM
71661251
Created by admin on Sat Dec 16 02:51:31 GMT 2023 , Edited by admin on Sat Dec 16 02:51:31 GMT 2023
PRIMARY
Related Record Type Details
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> INHIBITOR
IC50
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
ALPHA-1-ACID GLYCOPROTEIN
BINDER->LIGAND
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
HCV NS5A
TARGET -> INHIBITOR
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> INHIBITOR
IC50
OATP-8
TRANSPORTER -> INHIBITOR
IC50
Related Record Type Details
Structure of ELBASVIR
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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