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Details

Stereochemistry ABSOLUTE
Molecular Formula C49H54N8O8
Molecular Weight 883.0019
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VELPATASVIR

SMILES

COC[C@H]1C[C@H](N(C1)C(=O)[C@H](NC(=O)OC)C2=CC=CC=C2)C3=NC=C(N3)C4=CC5=C(C=C4)C6=CC7=C(C=C6OC5)C8=C(C=C7)N=C(N8)[C@@H]9CC[C@H](C)N9C(=O)[C@@H](NC(=O)OC)C(C)C

InChI

InChIKey=FHCUMDQMBHQXKK-CDIODLITSA-N
InChI=1S/C49H54N8O8/c1-26(2)41(54-48(60)63-5)47(59)57-27(3)12-17-38(57)45-51-36-16-14-30-20-35-33-15-13-31(19-32(33)25-65-40(35)21-34(30)43(36)53-45)37-22-50-44(52-37)39-18-28(24-62-4)23-56(39)46(58)42(55-49(61)64-6)29-10-8-7-9-11-29/h7-11,13-16,19-22,26-28,38-39,41-42H,12,17-18,23-25H2,1-6H3,(H,50,52)(H,51,53)(H,54,60)(H,55,61)/t27-,28-,38-,39-,41-,42+/m0/s1

HIDE SMILES / InChI

Molecular Formula C49H54N8O8
Molecular Weight 883.0019
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Velpatasvir (VEL; GS-5816) is an inhibitor of HCV NS5A protein, it demonstrated favourable in vitro and in vivo properties, including potent antiviral activity against hepatitis C virus genotypes 1 to 6 replicon, good metabolic stability, low systemic clearance, and adequate bioavailability and physicochemical properties to warrant clinical evaluation. Velpatasvir is used together with sofosbuvir in the treatment of hepatitis C infection of all six major genotypes. A once-daily, single-tablet, pangenotypic regimen comprising the HCV NS5B polymerase inhibitor sofosbuvir and the HCV NS5A inhibitor velpatasvir (sofosbuvir/ velpatasvir; Epclusa) has recently been approved for the treatment of adults with chronic HCV genotype 1, 2, 3, 4, 5 or 6 infection in the USA, EU and Canada.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.014 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Epclusa
PubMed

PubMed

TitleDatePubMed
Sofosbuvir/Velpatasvir: A Review in Chronic Hepatitis C.
2016 Oct
Preclinical Pharmacokinetics and First-in-Human Pharmacokinetics, Safety, and Tolerability of Velpatasvir, a Pangenotypic Hepatitis C Virus NS5A Inhibitor, in Healthy Subjects.
2017 May
Patents

Sample Use Guides

In Vivo Use Guide
Recommended dosage: One tablet (400 mg of sofosbuvir and 100 mg of velpatasvir) taken orally once daily with or without food
Route of Administration: Oral
In Vitro Use Guide
Velpatasvir had mean EC50 values of 0.014, 0.016, 0.005–0.016, 0.002–0.006, 0.004, 0.009, 0.004, 0.021–0.054, 0.006–0.009 and 0.130 nmol/L against laboratory replicons with HCV genotypes 1a, 1b, 2a, 2b, 3a, 4a, 4d, 5a, 6a and 6e, respectively, and median EC50 values of 0.002–0.024 nmol/L against replicons containing NS5A from clinical isolates with HCV genotypes 1a, 1b, 2a, 2b, 3a, 4a, 4d, 4r, 5a, 6a and 6e.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:46:10 UTC 2019
Edited
by admin
on Mon Oct 21 19:46:10 UTC 2019
Record UNII
KCU0C7RS7Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VELPATASVIR
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
VELPATASVIR [INN]
Common Name English
VELPATASVIR [WHO-DD]
Common Name English
EPCLUSA COMPONENT VELPATASVIR
Brand Name English
VELPATASVIR COMPONENT OF EPCLUSA
Brand Name English
VELPATASVIR [USAN]
Common Name English
VOSEVI COMPONENT VELPATASVIR
Common Name English
VELPATASVIR COMPONENT OF VOSEVI
Common Name English
GS-5816
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 554816
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
NCI_THESAURUS C281
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
WHO-ATC J05AP56
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
NDF-RT N0000191256
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
NCI_THESAURUS C783
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
WHO-ATC J05AP55
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
Code System Code Type Description
LactMed
1377049-84-7
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
NDF-RT
N0000190107
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]
NDF-RT
N0000190108
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY Organic Anion Transporting Polypeptide 1B3 Inhibitors [MoA]
CAS
1377049-84-7
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL3545062
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
NDF-RT
N0000190113
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
RXCUI
1799206
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
NDF-RT
N0000190109
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY Organic Anion Transporting Polypeptide 2B1 Inhibitors [MoA]
NDF-RT
N0000185503
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
PUBCHEM
67683363
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
NCI_THESAURUS
C152851
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
INN
9960
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
EVMPD
SUB180213
Created by admin on Mon Oct 21 19:46:10 UTC 2019 , Edited by admin on Mon Oct 21 19:46:10 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
IC50
TRANSPORTER -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
inhibit 30% at 10 ?M
IC50
TRANSPORTER -> INHIBITOR
IC50
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL
TRANSPORTER -> SUBSTRATE
IC50
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Blood-to-plasma ratio PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC