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Details

Stereochemistry ABSOLUTE
Molecular Formula C49H54F2N8O6.C3H6O
Molecular Weight 947.079
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEDIPASVIR ACETONE

SMILES

CC(C)=O.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=FJPWYOHJVGOKNZ-NDANSHMASA-N
InChI=1S/C49H54F2N8O6.C3H6O/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;1-3(2)4/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);1-2H3/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

Targets

Primary TargetPharmacologyConditionPotency
141.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HARVONI

Cmax

ValueDoseCo-administeredAnalytePopulation
531 ng/mL
45 mg 1 times / day multiple, oral
[NO STEREO] LEDIPASVIR plasma
Homo sapiens
323 ng/mL
90 mg 1 times / day steady-state, oral
[NO STEREO] LEDIPASVIR plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
9320 ng × h/mL
45 mg 1 times / day multiple, oral
[NO STEREO] LEDIPASVIR plasma
Homo sapiens
7290 ng × h/mL
90 mg 1 times / day steady-state, oral
[NO STEREO] LEDIPASVIR plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
47 h
90 mg 1 times / day steady-state, oral
[NO STEREO] LEDIPASVIR plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.2%
90 mg 1 times / day steady-state, oral
[NO STEREO] LEDIPASVIR plasma
Homo sapiens

Doses

PubMed

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.