LEDIPASVIR

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205834s010lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=23384816; http://www.ncbi.nlm.nih.gov/pubmed/?term=22314425

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 Target	Pharmacology	Condition	Potency
Nonstructural protein 5A 11 Target ID: CHEMBL3307224 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=23384816	Inhibitor 8504		141.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis C 42 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205834s010lbl.pdf	Primary		Approved 8583	HARVONI Approved Use Indicated for the treatment of patients with chronic hepatitis C virus (HCV) genotype 1, 4, 5, or 6 infection Launch Date 2014

C_max

Value	Dose	Co-administered	Analyte	Population
531 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31220349/	45 mg 1 times / day multiple, oral dose: 45 mg route of administration: Oral experiment type: MULTIPLE co-administered: [NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] LEDIPASVIR plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED
323 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/212477s000lbl.pdf	90 mg 1 times / day steady-state, oral dose: 90 mg route of administration: Oral experiment type: STEADY-STATE co-administered: [NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] LEDIPASVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
9320 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31220349/	45 mg 1 times / day multiple, oral dose: 45 mg route of administration: Oral experiment type: MULTIPLE co-administered: [NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] LEDIPASVIR plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: FED
7290 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/212477s000lbl.pdf	90 mg 1 times / day steady-state, oral dose: 90 mg route of administration: Oral experiment type: STEADY-STATE co-administered: [NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] LEDIPASVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
47 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/212477s000lbl.pdf	90 mg 1 times / day steady-state, oral dose: 90 mg route of administration: Oral experiment type: STEADY-STATE co-administered: [NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] LEDIPASVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/212477s000lbl.pdf	90 mg 1 times / day steady-state, oral dose: 90 mg route of administration: Oral experiment type: STEADY-STATE co-administered: [NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] PSI-7851\|[NO STEREO] SOFOSBUVIR	[NO STEREO] LEDIPASVIR plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
90 mg 1 times / day multiple, oral Highest studied dose Dose: 90 mg, 1 times / day Route: oral Route: multiple Dose: 90 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22314425	unhealthy, 49 years Health Status: unhealthy Age Group: 49 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/22314425	Sources: https://pubmed.ncbi.nlm.nih.gov/22314425

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:85089	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85089
ChemicalBook	CB52666650	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB52666650
MolPort	MolPort-039-138-665	https://www.molport.com/shop/molecule-link/MolPort-039-138-665
ZINC	ZINC000150338819	http://zinc15.docking.org/substances/ZINC000150338819

PubMed

Title	Date	PubMed
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.	2015-09	25937625
Treatment with ledipasvir and sofosbuvir improves patient-reported outcomes: Results from the ION-1, -2, and -3 clinical trials.	2015-06	25627448
Fixed-dose combination of sofosbuvir and ledipasvir for the treatment of chronic hepatitis C genotype 1.	2015-04	25676581
Virologic response following combined ledipasvir and sofosbuvir administration in patients with HCV genotype 1 and HIV co-infection.	2015-02-24	25706232
Ledipasvir and sofosbuvir: Interferon free therapy for hepatitis C virus genotype 1 infection.	2015-02-12	25674516
Changing the face of hepatitis C management - the design and development of sofosbuvir.	2015	25987834
Ledipasvir : a novel synthetic antiviral for the treatment of HCV infection.	2014-04	24593285

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.

Name

Type

Language

ledipasvir [INN]

Preferred Name

English

LEDIPASVIR

Official Name

English

HARVONI COMPONENT LEDIPASVIR

Brand Name

English

LEDIPASVIR [VANDF]

Common Name

English

LEDIPASVIR ACETONATE [JAN]

Common Name

English

LEDIPASVIR [MI]

Common Name

English

LEDIPASVIR [USAN]

Common Name

English

GS-5885

Code

English

Ledipasvir [WHO-DD]

Common Name

English

LEDIPASVIR [ORANGE BOOK]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J05AX65

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

NDF-RT

N0000191256

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

FDA ORPHAN DRUG

535916

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

EMA ASSESSMENT REPORTS

HARVONI (AUTHORIZED: HEPATITIS C, CHRONIC)

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

NCI_THESAURUS

C281

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

WHO-ATC

J05AP51

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

Code System Code Type Description

DRUG BANK

DB09027

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

PRIMARY

SMS_ID

100000143385

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PRIMARY

DRUG CENTRAL

4899

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

PRIMARY

NCI_THESAURUS

C129019

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

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LACTMED

Ledipasvir

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

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NDF-RT

N0000185503

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

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P-Glycoprotein Inhibitors [MoA]

MERCK INDEX

m11788

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INN

9796

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CAS

1256388-51-8

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FDA UNII

013TE6E4WV

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PRIMARY

RXCUI

1591922

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

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RxNorm

EPA CompTox

DTXSID90154829

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

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DAILYMED

013TE6E4WV

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

PRIMARY

CHEBI

85089

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

PRIMARY

ChEMBL

CHEMBL2374220

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

PRIMARY

EVMPD

SUB120165

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

PRIMARY

PUBCHEM

67505836

Created by admin on Wed Apr 02 08:33:24 GMT 2025 , Edited by admin on Wed Apr 02 08:33:24 GMT 2025

PRIMARY

NDF-RT

N0000190113

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

PRIMARY

Breast Cancer Resistance Protein Inhibitors [MoA]

WIKIPEDIA

Ledipasvir

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

PRIMARY

USAN

ZZ-132

Created by admin on Wed Apr 02 08:33:25 GMT 2025 , Edited by admin on Wed Apr 02 08:33:25 GMT 2025

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ACTIVE MOIETY


					013TE6E4WV

LEDIPASVIR

SALT/SOLVATE (PARENT)


					Z6GY125S9S

LEDIPASVIR DIACETONE

SALT/SOLVATE (PARENT)


					RT680T6HCQ

LEDIPASVIR D-TARTRATE

SALT/SOLVATE (PARENT)


					3J78ET35HX

LEDIPASVIR ACETONE

Details

SMILES

InChI

DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205834s010lbl.pdfCurator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=23384816; http://www.ncbi.nlm.nih.gov/pubmed/?term=22314425

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205834s010lbl.pdf
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=23384816; http://www.ncbi.nlm.nih.gov/pubmed/?term=22314425

C_max

T_1/2

F_unbound