U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C38H46F4N6O9S
Molecular Weight 838.8678
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLECAPREVIR

SMILES

CC(C)(C)[C@@]1([H])C(=O)N2C[C@@]([H])(C[C@@]2([H])C(=N[C@@]3(C[C@@]3([H])C(F)F)C(=NS(=O)(=O)C4(C)CC4)O)O)Oc5c(C(/C(/[H])=C(\[H])/CO[C@]6([H])CCC[C@@]6([H])OC(=N1)O)(F)F)nc7ccccc7n5

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
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

Curator's Comment:: Glecaprevir does not readily cross the blood:brain barrier.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.5 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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

1.501632E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1270 ng/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: PIBRENTASVIR
GLECAPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4500 ng × h/mL
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: PIBRENTASVIR
GLECAPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8.69 h
300 mg 1 times / day multiple, oral
dose: 300 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered: PIBRENTASVIR
GLECAPREVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse 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:
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:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Formulary Drug Review: Etelcalcetide.
2017 Nov
Glecaprevir + pibrentasvir (ABT493 + ABT-530) for the treatment of Hepatitis C.
2018 Jan
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

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
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
INN   USAN   WHO-DD  
USAN   INN  
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 [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 Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
FDA ORPHAN DRUG 550516
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
NDF-RT N0000182639
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL3545363
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
MERCK INDEX
M12026
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
FDA UNII
K6BUU8J72P
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
CAS
1365970-03-1
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
PUBCHEM
66828839
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
DRUG CENTRAL
5243
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
INN
10261
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
NCI_THESAURUS
C170029
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
EVMPD
SUB180954
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
LACTMED
Glecaprevir
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
DRUG BANK
DB13879
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY
RXCUI
1940635
Created by admin on Sat Jun 26 08:05:03 UTC 2021 , Edited by admin on Sat Jun 26 08:05:03 UTC 2021
PRIMARY