GRAZOPREVIR ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H50N6O9S
Molecular Weight	766.903
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@]1([H])OC(=O)N[C@H](C(=O)N3C[C@@]([H])(C[C@H]3C(=O)N[C@@]4(C[C@@]4([H])C=C)C(=O)NS(=O)(=O)C5CC5)OC6=NC7=CC(OC)=CC=C7N=C6CCCCC2)C(C)(C)C

InChI

InChIKey=OBMNJSNZOWALQB-NCQNOWPTSA-N

InChI=1S/C38H50N6O9S/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)/t21-,22-,24-,29+,30-,31-,38-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C38H50N6O9S
Molecular Weight	766.903
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208261Orig1s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28417245

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus NS3 protease/helicase 5 Target ID: CHEMBL4893 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24900473 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208261Orig1s000lbl.pdf	Inhibitor 8228		0.02 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatitis C 41 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=164dc02a-9180-426a-b8b5-04ab39d2bbd4&type=display	Primary		Approved 8360	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

Vendor/Aggregator	ID	URL
AA Blocks	AA009CAJ	https://www.aablocks.com/goods/Goods/detail?id=AA009CAJ
Aaron Chemicals	AR009D2B	http://www.aaronchem.com/1350514-68-9
Achemtek	0102-013826	http://www.achemtek.com/1350514-68-9
Aurum Pharmatech LLC	W-6087	http://www.Aurumpharmatech.com/Product/ProductDetails/W_6087
BLD Pharm	BD293153	http://www.bldpharm.com/products/1350514-68-9.html
BioCrick	BCC1762	http://www.biocrick.com/MK-5172-BCC1762.html
Boerchem	BC600762	http://www.boerchem.com/?product_43596.html
CSNpharm	CSN13898	https://www.csnpharm.com/products/mk-5172.html
Chem Scene	CS-1374	http://www.chemscene.com/1350514-68-9.html
Chemspace	CSSB00161189429	https://chem-space.com/CSSB00161189429
Excenen	EX-A2253	https://www.excenen.com/searchresultlist.php?id=1350514-68-9
Lab Network	LN01342722	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01342722
MedChem Express	HY-15298	https://www.medchemexpress.com/MK-5172.html
MuseChem	I001345	https://www.musechem.com/product/I001345.html
Selleck Chemicals	S3728	http://www.selleckchem.com/products/grazoprevir.html
Smolecule	S548927	http://www.smolecule.com/products/s548927
Synblock Inc	SB16740	http://www.synblock.com/product/1350514-68-9.html
THE BioTek	bt-288332	https://www.thebiotek.com/product/inhibitors/bt-288332
eNovation Chemicals	D521399	https://www.enovationchem.com/ProductDetails.asp?ProductID=D521399
iChemical	EBD3315156	http://www.ichemical.com/products/1350514-68-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed

Identification of the E5 open reading frame of human papillomavirus type 16.	1988 Mar	2828656
Elbasvir/Grazoprevir (Zepatier) for Hepatitis C Virus Infection.	2017 Mar 15	28318208
Elbasvir/Grazoprevir: A Review in Chronic HCV Genotypes 1 and 4.	2017 May	28417245
Elbasvir/grazoprevir does not worsen renal function in patients with hepatitis C virus infection and pre-existing renal disease.	2017 Nov	28334495

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

Route of Administration: Oral

In Vitro Use Guide

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 `Thu Jul 06 14:08:11 UTC 2023` Edited by `admin` on `Thu Jul 06 14:08:11 UTC 2023`
Record UNII	8YE81R1X1J
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GRAZOPREVIR ANHYDROUS

Common Name

English

MK-5172

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, (1R,2S)-

Systematic Name

English

MK-5172 ANHYDROUS

Code

English

GRAZOPREVIR COMPONENT OF ZEPATIER

Common Name

English

ZEPATIER COMPONENT OF GRAZOPREVIR

Common Name

English

Grazoprevir [WHO-DD]

Common Name

English

grazoprevir [INN]

Common Name

English

GRAZOPREVIR [MI]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000182639

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

Code System Code Type Description

SMS_ID

100000160903

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

CAS

1350514-68-9

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

PRIMARY

NDF-RT

N0000190114

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

Cytochrome P450 3A Inhibitors [MoA]

INN

9857

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

PRIMARY

MERCK INDEX

M11947

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

FDA UNII

8YE81R1X1J

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

PRIMARY

EVMPD

SUB174126

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

PRIMARY

CAS

1206524-75-5

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

SUPERSEDED

NCI_THESAURUS

C175724

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

RXCUI

1871173

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

CAS

1356446-42-8

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

SUPERSEDED

EPA CompTox

DTXSID50159234

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

PRIMARY

NDF-RT

N0000182638

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

HCV NS3/4A Protease Inhibitors [MoA]

PUBCHEM

44603531

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

DAILYMED

8YE81R1X1J

Created by admin on Thu Jul 06 14:08:11 UTC 2023 , Edited by admin on Thu Jul 06 14:08:11 UTC 2023

PRIMARY

NDF-RT

N0000190113

Created by admin on Thu Jul 06 14:08:12 UTC 2023 , Edited by admin on Thu Jul 06 14:08:12 UTC 2023

PRIMARY

Breast Cancer Resistance Protein Inhibitors [MoA]

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					L0423Z5LDW

CYTOCHROME P450 2C8

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Qualification:

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					4O2AB118LA

GRAZOPREVIR

SOLVATE->ANHYDROUS


					1YV0492L5Z

MRP-3

TRANSPORTER -> SUBSTRATE

Qualification:

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Amount:


					PUO0521HZV

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METABOLIC ENZYME -> INHIBITOR

Qualification:

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Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE


					AIN96D6SGL

OATP1B1

TRANSPORTER -> SUBSTRATE


					4O2AB118LA

GRAZOPREVIR

SALT/SOLVATE -> PARENT


					4AF605U6JN

MRP-2

TRANSPORTER -> INHIBITOR

Qualification:

IC50

Amount:

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(33R,35S,91R,92R,5S)-5-(TERT-BUTYL)-17-METHOXY-4,7-DIOXO-2,8-DIOXA-6-AZA-1(2,3)-QUINOXALINA-3(3,1)-PYRROLIDINA-9(1,2)-CYCLOPROPANACYCLOTETRADECAPHANE-35-CARBOXAMIDE

METABOLITE -> PARENT


					X9Y2H2A8PW

GRAZOPREVIR METABOLITE M-10

METABOLITE -> PARENT

Interaction Type:

MAJOR

Qualification:

FECAL

Related Record Type Details


					8YE81R1X1J

GRAZOPREVIR ANHYDROUS

ACTIVE MOIETY

Name	Property Type	Parameters
Volume of Distribution	PHARMACOKINETIC

Biological Half-life	PHARMACOKINETIC

Tmax	PHARMACOKINETIC	ORAL ADMINISTRATION

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208261Orig1s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28417245

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/208261Orig1s000lbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/28417245