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Details

Stereochemistry ABSOLUTE
Molecular Formula C49H54F2N8O6.C4H6O6
Molecular Weight 1039.0887
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEDIPASVIR D-TARTRATE

SMILES

CC(C)[C@@]([H])(C(=O)N1CC2(CC2)C[C@@]1([H])c3ncc(-c4ccc5-c6ccc(cc6C(c5c4)(F)F)-c7ccc8c(c7)[nH]c([C@]9([H])[C@@]%10([H])CC[C@]([H])(C%10)N9C(=O)[C@]([H])(C(C)C)N=C(O)OC)n8)[nH]3)N=C(O)OC.[C@]([H])([C@@]([H])(C(=O)O)O)(C(=O)O)O

InChI

InChIKey=ZQVLPYMRXLPMDX-KEAIDYLOSA-N
InChI=1S/C49H54F2N8O6.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/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);1-2,5-6H,(H,7,8)(H,9,10)/t29-,30+,38-,39-,40-,41-;1-,2-/m00/s1

HIDE SMILES / InChI

Molecular Formula C4H6O6
Molecular Weight 150.087
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C49H54F2N8O6
Molecular Weight 889.0017
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 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

1412899200000
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
Health Status: unhealthy
Age Group: 49 years
Sex: M+F
Sources:
PubMed

PubMed

TitleDatePubMed
Changing the face of hepatitis C management - the design and development of sofosbuvir.
2015
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 Fri Jun 25 22:35:54 UTC 2021
Edited
by admin
on Fri Jun 25 22:35:54 UTC 2021
Record UNII
RT680T6HCQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEDIPASVIR D-TARTRATE
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
CAS
1502654-87-6
Created by admin on Fri Jun 25 22:35:54 UTC 2021 , Edited by admin on Fri Jun 25 22:35:54 UTC 2021
NON-SPECIFIC STOICHIOMETRY
FDA UNII
RT680T6HCQ
Created by admin on Fri Jun 25 22:35:54 UTC 2021 , Edited by admin on Fri Jun 25 22:35:54 UTC 2021
PRIMARY
CAS
1499193-68-8
Created by admin on Fri Jun 25 22:35:54 UTC 2021 , Edited by admin on Fri Jun 25 22:35:54 UTC 2021
PRIMARY
PUBCHEM
78357794
Created by admin on Fri Jun 25 22:35:54 UTC 2021 , Edited by admin on Fri Jun 25 22:35:54 UTC 2021
PRIMARY
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