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Details

Stereochemistry ABSOLUTE
Molecular Formula C49H54F2N8O6
Molecular Weight 888.9999
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEDIPASVIR

SMILES

COC(=O)N[C@@H](C(C)C)C(=O)N1CC2(CC2)C[C@H]1C3=NC=C(N3)C4=CC=C5C(=C4)C(F)(F)C6=C5C=CC(=C6)C7=CC8=C(C=C7)N=C(N8)[C@@H]9[C@H]%10CC[C@H](C%10)N9C(=O)[C@@H](NC(=O)OC)C(C)C

InChI

InChIKey=VRTWBAAJJOHBQU-KMWAZVGDSA-N
InChI=1S/C49H54F2N8O6/c1-24(2)39(56-46(62)64-5)44(60)58-23-48(15-16-48)21-38(58)42-52-22-37(55-42)28-9-13-32-31-12-8-26(18-33(31)49(50,51)34(32)19-28)27-10-14-35-36(20-27)54-43(53-35)41-29-7-11-30(17-29)59(41)45(61)40(25(3)4)57-47(63)65-6/h8-10,12-14,18-20,22,24-25,29-30,38-41H,7,11,15-17,21,23H2,1-6H3,(H,52,55)(H,53,54)(H,56,62)(H,57,63)/t29-,30+,38-,39-,40-,41-/m0/s1

HIDE SMILES / InChI

Description

Ledipasvir is an inhibitor of the Hepatitis C Virus (HCV) NS5A protein required for viral RNA replication and assembly of HCV virions. Approved in October 2014 by the FDA, ledipasvir and sofosbuvir (tradename Harvoni) are direct-acting antiviral agents indicated for the treatment of HCV genotype 1 with or without cirrhosis.

CNS Activity

Originator

Approval Year

Target Info

Target Info

Primary TargetPharmacologyConditionPotency
141.0 nM [EC50]
Condition Info

Condition Info

ConditionModalityTargetsHighest PhaseProduct
Primary
HARVONI
PMID

PMID

TitleDatePMID
Ledipasvir : a novel synthetic antiviral for the treatment of HCV infection.
2014 Apr
Changing the face of hepatitis C management - the design and development of sofosbuvir.
2015
Fixed-dose combination of sofosbuvir and ledipasvir for the treatment of chronic hepatitis C genotype 1.
2015 Apr
Ledipasvir and sofosbuvir: Interferon free therapy for hepatitis C virus genotype 1 infection.
2015 Feb 12
Treatment with ledipasvir and sofosbuvir improves patient-reported outcomes: Results from the ION-1, -2, and -3 clinical trials.
2015 Jun
Virologic response following combined ledipasvir and sofosbuvir administration in patients with HCV genotype 1 and HIV co-infection.
2015 Mar 24-31
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.
2015 Sep
Patent

Patent

Sample Use Guides

In Vivo Use Guide
One tablet (90 mg of ledipasvir and 400 mg of sofosbuvir) taken orally once daily with or without food. Recommended treatment duration: treatment-naive with or without cirrhosis: 12 week. Treatment-experienced without cirrhosis: 12 weeks. Treatment-experienced with cirrhosis: 24 weeks. A dose recommendation cannot be made for patients with severe renal impairment or end stage renal disease.
Route of Administration: Oral
In Vitro Use Guide
Ledipasvir inhibitory activity in vitro was characterized by EC50 of 0.031, 0.004, 10.8, 10.1 and 0.045 nM against GT1a, GT1b, GT2a, GT31 and GT4a, respectively.
Name Type Language
LEDIPASVIR
DASH   INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
HARVONI COMPONENT LEDIPASVIR
Brand Name English
LEDIPASVIR [VANDF]
Common Name English
LEDIPASVIR ACETONATE [JAN]
Common Name English
LEDIPASVIR [INN]
Common Name English
LEDIPASVIR COMPONENT OF HARVONI
Brand Name English
LEDIPASVIR [WHO-DD]
Common Name English
LEDIPASVIR [USAN]
Common Name English
GS-5885
Code English
Classification Tree Code System Code
WHO-ATC J05AX65
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
NDF-RT N0000191256
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
EMA ASSESSMENT REPORTS HARVONI (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
Code System Code Type Description
DRUG BANK
DB09027
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
NCI_THESAURUS
C129019
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
NDF-RT
N0000185503
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY P-Glycoprotein Inhibitors [MoA]
EPA CompTox
1256388-51-8
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
INN
9796
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
CAS
1256388-51-8
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
RXCUI
1591922
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY RxNorm
LactMed
1256388-51-8
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
ChEMBL
CHEMBL2374220
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
EVMPD
SUB120165
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY
PUBCHEM
67505836
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY SWITZERF
NDF-RT
N0000190113
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
WIKIPEDIA
Ledipasvir
Created by admin on Tue Mar 06 11:02:46 UTC 2018 , Edited by admin on Tue Mar 06 11:02:46 UTC 2018
PRIMARY