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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

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

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
141.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HARVONI
PubMed

PubMed

TitleDatePubMed
Fixed-dose combination of sofosbuvir and ledipasvir for the treatment of chronic hepatitis C genotype 1.
2015 Apr
Patents

Patents

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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:48:28 UTC 2019
Edited
by admin
on Mon Oct 21 19:48:28 UTC 2019
Record UNII
013TE6E4WV
Record Status Validated (UNII)
Record Version
  • Download
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 Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
NDF-RT N0000191256
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
FDA ORPHAN DRUG 535916
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
EMA ASSESSMENT REPORTS HARVONI (AUTHORIZED: HEPATITIS C, CHRONIC)
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
NCI_THESAURUS C281
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
WHO-ATC J05AP51
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
Code System Code Type Description
DRUG BANK
DB09027
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
NCI_THESAURUS
C129019
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
NDF-RT
N0000185503
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY P-Glycoprotein Inhibitors [MoA]
EPA CompTox
1256388-51-8
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
INN
9796
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
CAS
1256388-51-8
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
RXCUI
1591922
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY RxNorm
LactMed
1256388-51-8
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
ChEMBL
CHEMBL2374220
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
EVMPD
SUB120165
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
PUBCHEM
67505836
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
NDF-RT
N0000190113
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
WIKIPEDIA
Ledipasvir
Created by admin on Mon Oct 21 19:48:28 UTC 2019 , Edited by admin on Mon Oct 21 19:48:28 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
LDV is a substrate for P-gp and BCRP in vitro (AD-256-2144 and AD-256-2150).
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
LDV is a substrate for P-gp and BCRP in vitro (AD-256-2144 and AD-256-2150).
BINDER->LIGAND
LDV is >99.8% bound to human plasma proteins when determined in vitro with equilibrium dialysis. In agreement with in vitro data, LDV protein binding was ‰ 98% in healthy subjects and in subjects with renal or hepatic impairment.
BINDING
EXCRETED UNCHANGED
Unchanged LDV was the major component excreted in feces and accounted for a mean of 70% of the administered dose, but no unchanged parent drug was detected in urine.
FECAL
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ONCE-DAILY DOSING

Tmax PHARMACOKINETIC ORAL ADMINISTRATION