ELBASVIR

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 Search

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

Description
Sources: http://www.merck.com/product/usa/pi_circulars/z/zepatier/zepatier_pi.pdf | https://www.ncbi.nlm.nih.gov/pubmed/26933896 | https://www.ncbi.nlm.nih.gov/pubmed/26926625

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Nonstructural protein 5A 11 Target ID: CHEMBL3307224 Sources: http://www.merck.com/product/usa/pi_circulars/z/zepatier/zepatier_pi.pdf	Inhibitor 8297		5.0 pM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis C 42 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2016/208261Orig1s000LBL.pdf	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 1.45393923E12

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Grazoprevir + elbasvir for the treatment of hepatitis C virus infection.	2016	26933896
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	26926625

Patents

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.

Name

Type

Language

ELBASVIR

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