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Chemistry

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Also known as: 1256388-51-8, Gs-5885, Gs5885, Ledipasvir acetonate, Gs 5885, Ledipasvir [usan]

Molecular Formula

C₄₉H₅₄F₂N₈O₆

Molecular Weight

889.0 g/mol

InChI Key

VRTWBAAJJOHBQU-KMWAZVGDSA-N

FDA UNII

013TE6E4WV

Ledipasvir is an orally available inhibitor of the hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex, with potential activity against HCV. Upon oral administration and after intracellular uptake, ledipasvir binds to and blocks the activity of the NS5A protein. This results in the disruption of the viral RNA replication complex, blockage of HCV RNA production, and inhibition of viral replication. NS5A, a zinc-binding and proline-rich hydrophilic phosphoprotein, plays a crucial role in HCV RNA replication. HCV is a small, enveloped, single-stranded RNA virus belonging to the Flaviviridae family; HCV infection is associated with the development of hepatocellular carcinoma (HCC).

Ledipasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of ledipasvir is as a P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor.

1 2D Structure

Ledipasvir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl N-[(2S)-1-[(6S)-6-[5-[9,9-difluoro-7-[2-[(1R,3S,4S)-2-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]-2-azabicyclo[2.2.1]heptan-3-yl]-3H-benzimidazol-5-yl]fluoren-2-yl]-1H-imidazol-2-yl]-5-azaspiro[2.4]heptan-5-yl]-3-methyl-1-oxobutan-2-yl]carbamate

2.1.2 InChI

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

2.1.3 InChI Key

VRTWBAAJJOHBQU-KMWAZVGDSA-N

2.1.4 Canonical SMILES

CC(C)C(C(=O)N1CC2(CC2)CC1C3=NC=C(N3)C4=CC5=C(C=C4)C6=C(C5(F)F)C=C(C=C6)C7=CC8=C(C=C7)N=C(N8)C9C1CCC(C1)N9C(=O)C(C(C)C)NC(=O)OC)NC(=O)OC

2.1.5 Isomeric SMILES

CC(C)[C@@H](C(=O)N1CC2(CC2)C[C@H]1C3=NC=C(N3)C4=CC5=C(C=C4)C6=C(C5(F)F)C=C(C=C6)C7=CC8=C(C=C7)N=C(N8)[C@@H]9[C@H]1CC[C@H](C1)N9C(=O)[C@H](C(C)C)NC(=O)OC)NC(=O)OC

2.2 Other Identifiers

2.2.1 UNII

013TE6E4WV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Gs-5885

2. Gs5885

3. Ledipasvir Acetonate

4. Methyl ((1s)-1-((1r,3s,4s)-3-(5-(9,9-difluoro-7-(2-((6s)-5-(n-(methoxycarbonyl)- L-valyl)-5-azaspiro(2.4)hept-6-yl)-1h-imidazol-4-yl)-9h-fluoren-2-yl)-1h-benzimidazol-2-yl)-2-azabicyclo(2.2.1)heptane-2-carbonyl)-2-methylpropyl)carbamate

2.3.2 Depositor-Supplied Synonyms

1. 1256388-51-8

2. Gs-5885

3. Gs5885

4. Ledipasvir Acetonate

5. Gs 5885

6. Ledipasvir [usan]

7. Chebi:85089

8. Who 9796

9. 013te6e4wv

10. Ledipasvir (usan)

11. Unii-013te6e4wv

12. Methyl N-[(2s)-1-[(6s)-6-[5-[9,9-difluoro-7-[2-[(1r,3s,4s)-2-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]-2-azabicyclo[2.2.1]heptan-3-yl]-3h-benzimidazol-5-yl]fluoren-2-yl]-1h-imidazol-2-yl]-5-azaspiro[2.4]heptan-5-yl]-3-methyl-1-oxobutan-2-yl]carbamate

13. Methyl N-[(2s)-1-[(6s)-6-[5-[9,9-difluoro-7-[2-[(1s,2s,4r)-3-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]-3-azabicyclo[2.2.1]heptan-2-yl]-3h-benzimidazol-5-yl]fluoren-2-yl]-1h-imidazol-2-yl]-5-azaspiro[2.4]heptan-5-yl]-3-methyl-1-oxobutan-2-yl]carbamate

14. Methyl [(2s)-1-{(6s)-6-[4-(9,9-difluoro-7-{2-[(1r,3s,4s)-2-{(2s)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl}-2-azabicyclo[2.2.1]hept-3-yl]-1h-benzimidazol-5-yl}-9h-fluoren-2-yl)-1h-imidazol-2-yl]-5-azaspiro[2.4]hept-5-yl}-3-methyl-1-oxobutan-2-yl]carbamate

15. Ledipasvir Acetonate [jan]

16. Ledipasvir [usan:inn]

17. Ledipasvir [mi]

18. Ledipasvir [inn]

19. Ledipasvir [vandf]

20. Ledipasvir [who-dd]

21. Schembl2706494

22. Chembl2374220

23. Ledipasvir [orange Book]

24. Schembl15116943

25. Gtpl11271

26. Dtxsid90154829

27. Ex-a411

28. Harvoni (ledipasvir + Sofosbuvir)

29. Harvoni Component Ledipasvir

30. Bdbm50505966

31. Mfcd25976756

32. Ledipasvir Component Of Harvoni

33. Zinc150338819

34. Cs-1653

35. Db09027

36. Ncgc00378990-02

37. Ncgc00378990-05

38. Ac-28378

39. As-56214

40. Hy-15602

41. Methyl ((1s)-1-((1r,3s,4s)-3-(5-(9,9-difluoro-7-(2-((6s)-5-(n-(methoxycarbonyl)- L-valyl)-5-azaspiro(2.4)hept-6-yl)-1h-imidazol-4-yl)-9h-fluoren-2-yl)-1h-benzimidazol-2-yl)-2-azabicyclo(2.2.1)heptane-2-carbonyl)-2-methylpropyl)carbamate

42. (non-isotopelabelled)ledipasvir-13c2, D6

43. D10442

44. Q15409409

45. 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-methylpropyl)-, Methyl Ester

46. Methyl ((s)-1-((s)-6-(5-(9,9-difluoro-7-(2-((1r,3s,4s)-2-((methoxycarbonyl)-l-valyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1h-benzo[d]imidazol-6-yl)-9h-fluoren-2-yl)-1h-imidazol-2-yl)-5-azaspiro[2, Aldrichcpr

47. Methyl ((s)-1-((s)-6-(5-(9,9-difluoro-7-(2-((1r,3s,4s)-2-((methoxycarbonyl)-l-valyl)-2-azabicyclo[2.2.1]heptan-3-yl)-1h-benzo[d]imidazol-6-yl)-9h-fluoren-2-yl)-1h-imidazol-2-yl)-5-azaspiro[2.4]heptan-5-yl)-3-methyl-1-oxobutan-2-yl)carbamate

48. Methyl N-[(1s)-1-[(5s)-5-[5-[9,9-difluoro-7-[2-[(1s,2s,4r)-3-[(2s)-2-(methoxycarbonylamino)-3-methyl-butanoyl]-3-azabicyclo[2.2.1]heptan-2-yl]-3h-benzimidazol-5-yl]fluoren-2-yl]-1h-imidazol-2-yl]-6-azaspiro[2.4]heptane-6-carbonyl]-2-methyl-propyl]carbamate

49. Methyl=[(2s)-1-[(6s)-6-[5-[9,9-difluoro-7-[2-[(1r,3s,4s)-2-[n-(methoxycarbonyl)-l-valyl]-2-azabicyclo[2.2.1]heptane-3-yl]-1h-benzoimidazole-6-yl]-9h-fluorene-2-yl]-1h-imidazole-2-yl]-5-azaspiro[2.4]heptane-5-yl]-3-methyl-1-oxobutane-2-yl]carbamate

2.4 Create Date

2012-11-30

3 Chemical and Physical Properties

Molecular Formula	C₄₉H₅₄F₂N₈O₆
Molecular Weight	889.0 g/mol
XLogP3	7.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	12
Exact Mass	888.41343780 g/mol
Monoisotopic Mass	888.41343780 g/mol
Topological Polar Surface Area	175 Å²
Heavy Atom Count	65
Formal Charge	0
Complexity	1820
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

When used in combination with the antiviral medication [sofosbuvir] as the commercially available product Harvoni, ledipasvir is indicated for the treatment of HCV genotypes 1, 4, 5, and 6 with or without [ribavirin] depending on the level of liver damage or cirrhosis. Its use has also proven successful in the treatment of HCV in patients co-infected with HIV.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ledipasvir acts against HCV and is categorized as a direct-acting antiviral agent (DAA). At a dose of 120 mg twice daily (2.67 times the maximum recommended dosage), ledipasvir does not prolong QTc interval to any clinically relevant extent.

5.2 MeSH Pharmacological Classification

Antiviral Agents

Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

LEDIPASVIR

5.3.2 FDA UNII

013TE6E4WV

5.3.3 Pharmacological Classes

Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors

5.4 Absorption, Distribution and Excretion

Absorption

When given orally, ledipasvir reaches its maximum plasma concentration in about 4 to 4.5 hours with a maximum concentration (Cmax) of 323 ng/mL.

Route of Elimination

Following a single 90 mg oral dose of [14C]-ledipasvir, mean total recovery of the [14C]-radioactivity in feces and urine was approximately 87%, with most of the radioactive dose recovered from feces (approximately 86%). Unchanged ledipasvir excreted in feces accounted for a mean of 70% of the administered dose and the oxidative metabolite M19 accounted for 2.2% of the dose. These data indicate that biliary excretion of unchanged ledipasvir is a major route of elimination, with renal excretion being a minor pathway (approximately 1%).

5.5 Metabolism/Metabolites

In vitro, no detectable metabolism of ledipasvir was observed by human CYP1A2, CYP2C8, CYP2C9, CYP2C19, CYP2D6, and CYP3A4. Evidence of slow oxidative metabolism via an unknown mechanism has been observed. Following a single dose of 90 mg [14C]-ledipasvir, systemic exposure was almost exclusively to the parent drug (>98%). Unchanged ledipasvir is the major species present in feces.

5.6 Biological Half-Life

The median terminal half-life of ledipasvir is 47 hours.

5.7 Mechanism of Action

Ledipasvir is an inhibitor of the Hepatitis C Virus (HCV) NS5A protein required for viral RNA replication and assembly of HCV virions. Although its exact mechanism of action is unknown, it is postulated to prevent hyperphosphorylation of NS5A which is required for viral production.

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