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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
    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 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.

    API Reference Price

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    24-Feb-2021
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    ABOUT THIS PAGE

    Harvoni Manufacturers

    A Harvoni manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Harvoni, including repackagers and relabelers. The FDA regulates Harvoni manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Harvoni API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

    click here to find a list of Harvoni manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

    Harvoni Suppliers

    A Harvoni supplier is an individual or a company that provides Harvoni active pharmaceutical ingredient (API) or Harvoni finished formulations upon request. The Harvoni suppliers may include Harvoni API manufacturers, exporters, distributors and traders.

    click here to find a list of Harvoni suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

    Harvoni USDMF

    A Harvoni DMF (Drug Master File) is a document detailing the whole manufacturing process of Harvoni active pharmaceutical ingredient (API) in detail. Different forms of Harvoni DMFs exist exist since differing nations have different regulations, such as Harvoni USDMF, ASMF (EDMF), JDMF, CDMF, etc.

    A Harvoni DMF submitted to regulatory agencies in the US is known as a USDMF. Harvoni USDMF includes data on Harvoni's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Harvoni USDMF is kept confidential to protect the manufacturer’s intellectual property.

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    Harvoni WC

    A Harvoni written confirmation (Harvoni WC) is an official document issued by a regulatory agency to a Harvoni manufacturer, verifying that the manufacturing facility of a Harvoni active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Harvoni APIs or Harvoni finished pharmaceutical products to another nation, regulatory agencies frequently require a Harvoni WC (written confirmation) as part of the regulatory process.

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    Harvoni NDC

    National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Harvoni as an active pharmaceutical ingredient (API).

    Finished drug products

    The FDA updates the NDC directory daily. The NDC numbers for Harvoni API and other APIs are published in this directory by the FDA.

    Unfinished drugs

    The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

    Pharmaceutical companies that manufacture Harvoni as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

    Compounded drug products

    The NDC directory also contains data on finished compounded human drug products that contain Harvoni and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Harvoni NDC to their finished compounded human drug products, they may choose to do so.

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    Harvoni GMP

    Harvoni Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

    GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

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    Harvoni CoA

    A Harvoni CoA (Certificate of Analysis) is a formal document that attests to Harvoni's compliance with Harvoni specifications and serves as a tool for batch-level quality control.

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    Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
    For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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