GLECAPREVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C38H46F4N6O9S
Molecular Weight	838.865
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@H](N(C1)C(=O)[C@@H](NC(=O)O[C@]3([H])CCC[C@@]3([H])OC\C=C\C(F)(F)C4=NC5=CC=CC=C5N=C4O2)C(C)(C)C)C(=O)N[C@@]6(C[C@H]6C(F)F)C(=O)NS(=O)(=O)C7(C)CC7

InChI

InChIKey=MLSQGNCUYAMAHD-ITNVBOSISA-N

InChI=1S/C38H46F4N6O9S/c1-35(2,3)28-32(50)48-19-20(17-24(48)30(49)46-37(18-21(37)29(39)40)33(51)47-58(53,54)36(4)14-15-36)56-31-27(43-22-9-5-6-10-23(22)44-31)38(41,42)13-8-16-55-25-11-7-12-26(25)57-34(52)45-28/h5-6,8-10,13,20-21,24-26,28-29H,7,11-12,14-19H2,1-4H3,(H,45,52)(H,46,49)(H,47,51)/b13-8+/t20-,21+,24+,25-,26-,28-,37-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209394s003lbl.pdf | https://www.drugbank.ca/drugs/DB13879 | https://www.ncbi.nlm.nih.gov/pubmed/29084747

Glecaprevir is a direct acting antiviral agent and Hepatitis C virus (HCV) NS3/4A protease inhibitor that targets the the viral RNA replication. In combination with Pibrentasvir, glecaprevir is a useful therapy for patients who experienced therapeutic failure from other NS3/4A protease inhibitors. It demonstrates a high genetic barrier against resistance mutations of the virus. Glecaprevir is available as an oral combination therapy with Pibrentasvir under the brand name Mavyret. On 3 August 2017 the FDA approved the combination for hepatitis C treatment. Mavyret is indicated for the treatment of adult patients with chronic hepatitis C virus (HCV) genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh A). Mavyret is also indicated for the treatment of adult patients with HCV genotype 1 infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor or an NS3/4A protease inhibitor (PI), but not both.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hepatitis C virus serine protease, NS3/NS4A 13 Target ID: CHEMBL2095231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/29084747	Inhibitor 8297		3.5 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis C 42 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209394s003lbl.pdf	Primary		Approved 8429	MAVYRET Approved Use MAVYRET is indicated for the treatment of adult patients with chronic hepatitis C virus (HCV) genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh A). MAVYRET is also indicated for the treatment of adult patients with HCV genotype 1 infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor or an NS3/4A protease inhibitor (PI), but not both. Launch Date 2017

C_max

Value	Dose	Co-administered	Analyte	Population
1270 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28800195	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: PIBRENTASVIR	PIBRENTASVIR	GLECAPREVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Co-administered	Analyte	Population
4500 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28800195	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: PIBRENTASVIR	PIBRENTASVIR	GLECAPREVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
8.69 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28800195	300 mg 1 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: PIBRENTASVIR	PIBRENTASVIR	GLECAPREVIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Doses

Dose	Population	Adverse events
700 mg 1 times / day multiple, oral Highest studied dose Dose: 700 mg, 1 times / day Route: oral Route: multiple Dose: 700 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26711747	unhealthy, 50.3 ± 9.04 years n = 9 Health Status: unhealthy Condition: chronic HCV infection Age Group: 50.3 ± 9.04 years Sex: M Population Size: 9 Sources: https://pubmed.ncbi.nlm.nih.gov/26711747	Sources: https://pubmed.ncbi.nlm.nih.gov/26711747

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA01EODH	https://www.aablocks.com/goods/Goods/detail?id=AA01EODH
Acadechem	ACDS-0781668	http://acadechemical.com/product/229214
Achemtek	0102-032388	http://achemtek.com/1365970-03-1-2
Acorn PharmaTech	ACN-041377	http://www.acornpharmatech.com/
Angel Pharmatech	AG317389	http://www.angelpharmatech.com/1365970-03-1.html
Ark Pharm	AK689356	http://www.arkpharminc.com/products/1365970-03-1.html
BOC Sciences	1365970-03-1	https://www.bocsci.com/glecaprevir-cas-1365970-03-1-item-7083.html
BioChemPartner	BCP20700	http://www.biochempartner.com/1365970-03-1-BCP20700
Chem Scene	CS-8098	http://www.chemscene.com/1365970-03-1.html
ChemShuttle	186356	https://www.chemshuttle.com/catalogsearch/result/?q=1365970-03-1&cat=
Chemspace	CSSB00161189601	https://chem-space.com/CSSB00161189601
Chemspace	CSSB02125554580	https://chem-space.com/CSSB02125554580
DC Chemicals	DC10818	http://www.dcchemicals.com/product_show-Glecaprevir.html
Excenen	EX-A1940	https://www.excenen.com/searchresultlist.php?id=1365970-03-1
Finetech	FT-0701278	http://www.finetechnology-ind.com/prod/detail/pub/1365970-03-1.html
MedChem Express	HY-17634	https://www.medchemexpress.com/Glecaprevir.html
MolPort	MolPort-046-418-346	https://www.molport.com/shop/molecule-link/MolPort-046-418-346
MolPort	MolPort-046-701-610	https://www.molport.com/shop/molecule-link/MolPort-046-701-610
MolPort	MolPort-046-702-254	https://www.molport.com/shop/molecule-link/MolPort-046-702-254
Selleck Chemicals	S5720	http://www.selleckchem.com/products/glecaprevir.html
Smolecule	S528936	http://www.smolecule.com/products/s528936
Smolecule	S895095	https://www.smolecule.com/products/s895095
Synblock Inc	SB19760	http://www.synblock.com/product/1365970-03-1.html
THE BioTek	bt-269105	https://www.thebiotek.com/product/inhibitors/bt-269105
THE BioTek	bt-505425	https://www.thebiotek.com/product/others/bt-505425
eNovation Chemicals	D621059	https://www.enovationchem.com/ProductDetails.asp?ProductID=D621059

PubMed

Title	Date	PubMed
Glecaprevir + pibrentasvir (ABT493 + ABT-530) for the treatment of Hepatitis C.	2018 Jan	29187007
Glecaprevir-Pibrentasvir for 8 or 12 Weeks in HCV Genotype 1 or 3 Infection.	2018 Jan 25	29365309

Patents

Sample Use Guides

In Vivo Use Guide

Each tablet of Mavyret (glecaprevir and pibrentasvir): 100 mg glecaprevir and 40 mg pibrentasvir. Recommended dosage: Three tablets (total daily dose: glecaprevir 300 mg and pibrentasvir 120 mg) taken orally once daily with food.

Route of Administration: Oral

In Vitro Use Guide

Glecaprevir inhibited the enzymatic activity of purified NS3/4A proteases from HCV genotypes 1 to 6 in vitro (half-maximal [50%] inhibitory concentration = 3.5 to 11.3 nM) and the replication of stable HCV subgenomic replicons containing proteases from genotypes 1 to 6 (50% effective concentration [EC50] = 0.21 to 4.6 nM). Glecaprevir had a median EC50 of 0.30 nM (range, 0.05 to 3.8 nM) for HCV replicons containing proteases from 40 samples from patients infected with HCV genotypes 1 to 5.

Name

Type

Language

GLECAPREVIR

Official Name

English

ABT-493

Code

English

A-12825760

Code

English

GLECAPREVIR [ORANGE BOOK]

Common Name

English

GLECAPREVIR [MI]

Common Name

English

MAVYRET COMPONENT GLECAPREVIR

Common Name

English

glecaprevir [INN]

Common Name

English

Glecaprevir [WHO-DD]

Common Name

English

GLECAPREVIR [USAN]

Common Name

English

A-1282576

Code

English

A-1282576.0

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

550516