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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=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
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

Curator's Comment: Low levels of C14-ledipasvir-derived radioactivity were observed in the CNS

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
141.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
HARVONI

Approved Use

Indicated for the treatment of patients with chronic hepatitis C virus (HCV) genotype 1, 4, 5, or 6 infection

Launch Date

1.41289914E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
323 ng/mL
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] LEDIPASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
531 ng/mL
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] LEDIPASVIR plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
7290 ng × h/mL
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] LEDIPASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9320 ng × h/mL
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] LEDIPASVIR plasma
Homo sapiens
population: UNHEALTHY
age: CHILD
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
47 h
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] LEDIPASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.2%
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] LEDIPASVIR plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
unhealthy, 49 years
n = 10
Health Status: unhealthy
Condition: genotype 1 hepatitis C
Age Group: 49 years
Sex: M+F
Population Size: 10
Sources:
PubMed

PubMed

TitleDatePubMed
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
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.
2015 Sep
Patents

Patents

Sample Use Guides

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
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 Thu Jul 06 23:46:43 UTC 2023
Edited
by admin
on Thu Jul 06 23:46:43 UTC 2023
Record UNII
3J78ET35HX
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 23:46:44 UTC 2023 , Edited by admin on Thu Jul 06 23:46:44 UTC 2023
PRIMARY
FDA UNII
3J78ET35HX
Created by admin on Thu Jul 06 23:46:44 UTC 2023 , Edited by admin on Thu Jul 06 23:46:44 UTC 2023
PRIMARY
CAS
1441674-54-9
Created by admin on Thu Jul 06 23:46:44 UTC 2023 , Edited by admin on Thu Jul 06 23:46:44 UTC 2023
PRIMARY
PUBCHEM
78357793
Created by admin on Thu Jul 06 23:46:44 UTC 2023 , Edited by admin on Thu Jul 06 23:46:44 UTC 2023
PRIMARY
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