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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 of GLECAPREVIR

SMILES

CC(C)(C)[C@@H]1NC(=O)O[C@@H]2CCC[C@H]2OC\C=C\C(F)(F)C3=C(O[C@@H]4C[C@H](N(C4)C1=O)C(=O)N[C@@]5(C[C@H]5C(F)F)C(=O)NS(=O)(=O)C6(C)CC6)N=C7C=CC=CC7=N3

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

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

Description

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAVYRET
PubMed

PubMed

TitleDatePubMed
Retreatment of patients with treatment failure of direct-acting antivirals: Focus on hepatitis C virus genotype 1b.
2017 Dec 14
Formulary Drug Review: Etelcalcetide.
2017 Nov
Glecaprevir + pibrentasvir (ABT493 + ABT-530) for the treatment of Hepatitis C.
2018 Jan
Glecaprevir-Pibrentasvir for 8 or 12 Weeks in HCV Genotype 1 or 3 Infection.
2018 Jan 25
Effects of Renal Impairment and Hemodialysis on the Pharmacokinetics and Safety of the Glecaprevir and Pibrentasvir Combination in Hepatitis C Virus-Negative Subjects.
2018 Mar
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:48:49 UTC 2019
Edited
by admin
on Mon Oct 21 19:48:49 UTC 2019
Record UNII
K6BUU8J72P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLECAPREVIR
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
ABT-493
Code English
A-12825760
Code English
MAVYRET COMPONENT GLECAPREVIR
Common Name English
GLECAPREVIR [INN]
Common Name English
GLECAPREVIR [USAN]
Common Name English
A-1282576
Code English
A-1282576.0
Code English
GLECAPREVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AP57
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
FDA ORPHAN DRUG 550516
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
NDF-RT N0000182639
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL3545363
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
PRIMARY
CAS
1365970-03-1
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
PRIMARY
PUBCHEM
66828839
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
PRIMARY
INN
10261
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
PRIMARY
EVMPD
SUB180954
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
PRIMARY
RXCUI
1940635
Created by admin on Mon Oct 21 19:48:49 UTC 2019 , Edited by admin on Mon Oct 21 19:48:49 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
TRANSPORTER -> SUBSTRATE
BINDER->LIGAND
GLE is approximately 97.5% bound to human plasma proteins independent of concentration from 0.1 to 30 ?M (800 to 25,200 ng/mL).
TARGET -> INHIBITOR
ABT-493 demonstrates comparable acti vity against HCV replicons containing NS3 genes from genotype 1a, 1b, 2a, 3a, 4a, and 6a
EC50
TRANSPORTER -> INHIBITOR
INNOVATOR->PARENT
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MAJOR
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
blood-to-plasma ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC