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Details

Stereochemistry ACHIRAL
Molecular Formula C49H54F2N8O6.2C3H6O
Molecular Weight 1005.1581
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEDIPASVIR DIACETONE

SMILES

CC(C)=O.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=LXKDKHCANHWUPC-YGWQTYEPSA-N
InChI=1S/C49H54F2N8O6.2C3H6O/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;2*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);2*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

CNS Active
3913
Curator's Comment: Low levels of C14-ledipasvir-derived radioactivity were observed in the CNS

Originator

Approval Year

2014
494
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 141.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

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:
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

Sourcing

Vendor/AggregatorIDURL
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

PubMed

TitleDatePubMed
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
Treatment with ledipasvir and sofosbuvir improves patient-reported outcomes: Results from the ION-1, -2, and -3 clinical trials.
2015 Jun
Virologic response following combined ledipasvir and sofosbuvir administration in patients with HCV genotype 1 and HIV co-infection.
2015 Mar 24-31
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.
2015 Sep
Patents

Patents

20100310512
5

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 12:07:34 GMT 2023
Edited
by admin
on Sat Dec 16 12:07:34 GMT 2023
Record UNII
Z6GY125S9S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEDIPASVIR DIACETONE
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
1502655-48-2
Created by admin on Sat Dec 16 12:07:34 GMT 2023 , Edited by admin on Sat Dec 16 12:07:34 GMT 2023
PRIMARY
FDA UNII
Z6GY125S9S
Created by admin on Sat Dec 16 12:07:34 GMT 2023 , Edited by admin on Sat Dec 16 12:07:34 GMT 2023
PRIMARY
PUBCHEM
92044391
Created by admin on Sat Dec 16 12:07:34 GMT 2023 , Edited by admin on Sat Dec 16 12:07:34 GMT 2023
PRIMARY
Related Record Type Details
Structure of LEDIPASVIR
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LEDIPASVIR
ACTIVE MOIETY
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