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    Harvoni

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    2D Structure
    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

    2D Structure

    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 Weight 889.0 g/mol
    Molecular Formula C49H54F2N8O6
    XLogP37.4
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count12
    Exact Mass888.41343780 g/mol
    Monoisotopic Mass888.41343780 g/mol
    Topological Polar Surface Area175 Ų
    Heavy Atom Count65
    Formal Charge0
    Complexity1820
    Isotope Atom Count0
    Defined Atom Stereocenter Count6
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.