LEDIPASVIR ACETONE

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 Search

SMILES

CC(C)=O.COC(=O)N[C@@H](C(C)C)C(=O)N1CC2(CC2)C[C@H]1C3=NC=C(N3)C4=CC5=C(C=C4)C6=C(C=C(C=C6)C7=CC=C8N=C(NC8=C7)[C@@H]9[C@H]%10CC[C@H](C%10)N9C(=O)[C@@H](NC(=O)OC)C(C)C)C5(F)F

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

Molecular Formula	C3H6O
Molecular Weight	58.0791
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C49H54F2N8O6
Molecular Weight	888.9999
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8297		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 8429	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
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

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 n = 10 Health Status: unhealthy Condition: genotype 1 hepatitis C Age Group: 49 years Sex: M+F Population Size: 10 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
Changing the face of hepatitis C management - the design and development of sofosbuvir.	2015	25987834
Fixed-dose combination of sofosbuvir and ledipasvir for the treatment of chronic hepatitis C genotype 1.	2015 Apr	25676581
Treatment with ledipasvir and sofosbuvir improves patient-reported outcomes: Results from the ION-1, -2, and -3 clinical trials.	2015 Jun	25627448
Virologic response following combined ledipasvir and sofosbuvir administration in patients with HCV genotype 1 and HIV co-infection.	2015 Mar 24-31	25706232
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.	2015 Sep	25937625

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 `Sat Dec 16 18:30:39 GMT 2023` Edited by `admin` on `Sat Dec 16 18:30:39 GMT 2023`
Record UNII	3J78ET35HX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LEDIPASVIR ACETONE

Common Name

English

CARBAMIC ACID, N-((1S)-1-(((6S)-6-(5-(9,9-DIFLUORO-7-(2-((1R,3S,4S)-2-((2S)-2-((METHOXYCARBONYL)AMINO)-3-METHYL-1-OXOBUTYL)-2-AZABICYCLO(2.2.1)HEPT-3-YL)-1H-BENZIMIDAZOL-6-YL)-9H-FLUOREN-2-YL)-1H-IMIDAZOL-2-YL)-5-AZASPIRO(2.4)HEPT-5-YL)CARBONYL)-2-METHYL

Systematic Name

English

Code System Code Type Description

SMS_ID

300000001120

Created by admin on Sat Dec 16 18:30:39 GMT 2023 , Edited by admin on Sat Dec 16 18:30:39 GMT 2023

PRIMARY

FDA UNII

3J78ET35HX

Created by admin on Sat Dec 16 18:30:39 GMT 2023 , Edited by admin on Sat Dec 16 18:30:39 GMT 2023

PRIMARY

CAS

1441674-54-9

Created by admin on Sat Dec 16 18:30:39 GMT 2023 , Edited by admin on Sat Dec 16 18:30:39 GMT 2023

PRIMARY

PUBCHEM

78357793

Created by admin on Sat Dec 16 18:30:39 GMT 2023 , Edited by admin on Sat Dec 16 18:30:39 GMT 2023

PRIMARY

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					013TE6E4WV

LEDIPASVIR

PARENT -> SALT/SOLVATE

Related Record Type Details


					013TE6E4WV

LEDIPASVIR

ACTIVE MOIETY

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