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Details

Stereochemistry ABSOLUTE
Molecular Formula C57H65F5N10O8
Molecular Weight 1113.1802
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIBRENTASVIR

SMILES

CO[C@H](C)[C@H](NC(=O)OC)C(=O)N1CCC[C@H]1C2=NC3=C(N2)C=C(F)C(=C3)[C@H]4CC[C@@H](N4C5=CC(F)=C(N6CCC(CC6)C7=CC=C(F)C=C7)C(F)=C5)C8=CC9=C(NC(=N9)[C@@H]%10CCCN%10C(=O)[C@@H](NC(=O)OC)[C@@H](C)OC)C=C8F

InChI

InChIKey=VJYSBPDEJWLKKJ-NLIMODCCSA-N
InChI=1S/C57H65F5N10O8/c1-29(77-3)49(67-56(75)79-5)54(73)70-19-7-9-47(70)52-63-41-25-35(37(59)27-43(41)65-52)45-15-16-46(72(45)34-23-39(61)51(40(62)24-34)69-21-17-32(18-22-69)31-11-13-33(58)14-12-31)36-26-42-44(28-38(36)60)66-53(64-42)48-10-8-20-71(48)55(74)50(30(2)78-4)68-57(76)80-6/h11-14,23-30,32,45-50H,7-10,15-22H2,1-6H3,(H,63,65)(H,64,66)(H,67,75)(H,68,76)/t29-,30-,45-,46-,47+,48+,49+,50+/m1/s1

HIDE SMILES / InChI

Molecular Formula C57H65F5N10O8
Molecular Weight 1113.1802
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Pibrentasvir is a direct acting antiviral agent and Hepatitis C virus (HCV) NS5A inhibitor that targets the the viral RNA replication and viron assembly. NS5A is a phosphoprotein that plays an essential role in replication, assembly and maturation of infectious viral proteins. The basal phosphorylated form of NS5A, which is maintained by C-terminal serine cluster, is key in ensuring its interaction with the viral capsid protein, or the core protein. By blocking this interaction, pibrentasvir inhibits the assembly of proteins and production of mature HCV particles. In the United States and Europe, Pibrentasvir is approved for use with glecaprevir as the combination drug glecaprevir/pibrentasvir (trade name Mavyret in the US and Maviret in the EU) for the treatment of hepatitis C. This fixed-dose combination therapy was FDA-approved in August 2017 to treat adults with chronic hepatitis C virus (HCV) genotypes 1-6 without cirrhosis (liver disease) or with mild cirrhosis, including patients with moderate to severe kidney disease and those who are on dialysis.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.0014 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAVYRET
PubMed

PubMed

TitleDatePubMed
In Vitro Antiviral Activity and Resistance Profile of the Next-Generation Hepatitis C Virus NS5A Inhibitor Pibrentasvir.
2017 May
Glecaprevir and Pibrentasvir in Patients with HCV and Severe Renal Impairment.
2017 Oct 12
Efficacy of NS5A Inhibitors Against Hepatitis C Virus Genotypes 1-7 and Escape Variants.
2018 Apr
Integrated Resistance Analysis of CERTAIN-1 and CERTAIN-2 Studies in Hepatitis C Virus-Infected Patients Receiving Glecaprevir and Pibrentasvir in Japan.
2018 Feb
Glecaprevir + pibrentasvir (ABT493 + ABT-530) for the treatment of Hepatitis C.
2018 Jan
Efficacy of Glecaprevir/Pibrentasvir for 8 or 12 Weeks in Patients With Hepatitis C Virus Genotype 2, 4, 5, or 6 Infection Without Cirrhosis.
2018 Mar
Patents

Patents

Sample Use Guides

In Vivo Use Guide
MAVYRET is a fixed-dose combination product containing glecaprevir 100 mg and pibrentasvir 40 mg in each tablet. The recommended oral dosage of MAVYRET is three tablets (total daily dose: glecaprevir 300 mg and pibrentasvir 120 mg) taken once daily with food.
Route of Administration: Oral
In Vitro Use Guide
According to HCV replicon assays, pibrentasvir has EC50 values ranging from 0.08-4.6 nM agaisnt laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4d, 5a, and 6a, or EC50 values of 0.5-4.3 pM against laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4b, 4d, 5a, 6a, 6e and 6p.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:47:33 UTC 2019
Edited
by admin
on Mon Oct 21 19:47:33 UTC 2019
Record UNII
2WU922TK3L
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIBRENTASVIR
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
ABT-530
Code English
MAVYRET COMPONENT PIBRENTASVIR
Common Name English
PIBRENTASVIR [USAN]
Common Name English
PIBRENTASVIR [JAN]
Common Name English
DIMETHYL N,N'-(((2R,5R)-1-(3,5-DIFLUORO-4-(4-(4-FLUOROPHENYL)PIPERIDIN-1-YL)PHENYL)PYRROLIDINE-2,5-DIYL)BIS((6-FLUORO-1H-BENZIMIDAZOLE-5,2-DIYL)((2S)-PYRROLIDINE-2,1-DIYL)((2S,3R)-3-METHOXY-1-OXOBUTANE-1,2-DIYL)))BISCARBAMATE
Systematic Name English
A-1325912.0
Code English
PIBRENTASVIR [INN]
Common Name English
PIBRENTASVIR [WHO-DD]
Common Name English
Classification Tree Code System Code
NDF-RT N0000191256
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
WHO-ATC J05AP57
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
FDA ORPHAN DRUG 550516
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
Code System Code Type Description
CAS
1353900-92-1
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
PRIMARY
ChEMBL
CHEMBL3545123
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
PRIMARY
PUBCHEM
58031952
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
PRIMARY
INN
10260
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
PRIMARY
RXCUI
1940636
Created by admin on Mon Oct 21 19:47:33 UTC 2019 , Edited by admin on Mon Oct 21 19:47:33 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
Blood-to-Plasma Ratio PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC