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    Paritaprevir

    ACTIVE PHARMA INGREDIENTS

    INTERMEDIATES

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    2D Structure
    Also known as: Veruprevir, Abt-450, Veruprevir anhydrous, 1216941-48-8, Abt450, 1221573-85-8
    Molecular Formula
    C40H43N7O7S
    Molecular Weight
    765.9  g/mol
    InChI Key
    UAUIUKWPKRJZJV-QPLHLKROSA-N
    FDA UNII
    OU2YM37K86
    Paritaprevir is an orally bioavailable, synthetic acylsulfonamide inhibitor of the hepatitis C virus (HCV) protease complex comprised of non-structural protein 3 and 4A (NS3/NS4A), with potential activity against HCV genotype 1. Upon administration, paritaprevir reversibly binds to the active center and binding site of the HCV NS3/NS4A protease and prevents NS3/NS4A protease-mediated polyprotein maturation. This disrupts both the processing of viral proteins and the formation of the viral replication complex, which inhibits viral replication in HCV genotype 1-infected host cells. NS3, a serine protease, is essential for the proteolytic cleavage of multiple sites within the HCV polyprotein and plays a key role during HCV ribonucleic acid (RNA) replication. NS4A is an activating factor for NS3. HCV is a small, enveloped, single-stranded RNA virus belonging to the Flaviviridae family, and infection is associated with the development of hepatocellular carcinoma (HCC).
    Paritaprevir is a Hepatitis C Virus NS3/4A Protease Inhibitor. The mechanism of action of paritaprevir is as a HCV NS3/4A Protease Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and UGT1A1 Inhibitor, and P-Glycoprotein Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,4R,6S,7Z,14S,18R)-N-cyclopropylsulfonyl-14-[(5-methylpyrazine-2-carbonyl)amino]-2,15-dioxo-18-phenanthridin-6-yloxy-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxamide
    2.1.2 InChI
    InChI=1S/C40H43N7O7S/c1-24-21-42-33(22-41-24)35(48)43-32-16-6-4-2-3-5-11-25-20-40(25,39(51)46-55(52,53)27-17-18-27)45-36(49)34-19-26(23-47(34)38(32)50)54-37-30-14-8-7-12-28(30)29-13-9-10-15-31(29)44-37/h5,7-15,21-22,25-27,32,34H,2-4,6,16-20,23H2,1H3,(H,43,48)(H,45,49)(H,46,51)/b11-5-/t25-,26-,32+,34+,40-/m1/s1
    2.1.3 InChI Key
    UAUIUKWPKRJZJV-QPLHLKROSA-N
    2.1.4 Canonical SMILES
    CC1=CN=C(C=N1)C(=O)NC2CCCCCC=CC3CC3(NC(=O)C4CC(CN4C2=O)OC5=NC6=CC=CC=C6C7=CC=CC=C75)C(=O)NS(=O)(=O)C8CC8
    2.1.5 Isomeric SMILES
    CC1=CN=C(C=N1)C(=O)N[C@H]2CCCCC/C=C\[C@@H]3C[C@]3(NC(=O)[C@@H]4C[C@H](CN4C2=O)OC5=NC6=CC=CC=C6C7=CC=CC=C75)C(=O)NS(=O)(=O)C8CC8
    2.2 Other Identifiers
    2.2.1 UNII
    OU2YM37K86
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. (2r,6s,12z,13as,14ar,16as)-n-(cyclopropylsulfonyl)-6-(5-methylpyrazin-2-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,6,7,8,9,10,11,13a,14,15,16,16atetradecahydrocyclopropa(e)pyrrolo(1,2-a)(1,4)diazacyclopentadecine-14a(5h)-carboxamide

    2. Abt 450

    3. Abt-450

    4. Abt450

    5. Paritaprevir Dihydrate

    6. Paritaprevir Hydrate

    7. Veruprevir

    8. Veruprevir Anhydrous

    2.3.2 Depositor-Supplied Synonyms

    1. Veruprevir

    2. Abt-450

    3. Veruprevir Anhydrous

    4. 1216941-48-8

    5. Abt450

    6. 1221573-85-8

    7. Ou2ym37k86

    8. (2r,6s,12z,13as,14ar,16as)-n-(cyclopropylsulfonyl)-6-(5-methylpyrazin-2-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,6,7,8,9,10,11,13a,14,15,16,16atetradecahydrocyclopropa(e)pyrrolo(1,2-a)(1,4)diazacyclopentadecine-14a(5h)-carboxamide

    9. Paritaprevir(abt-450)

    10. (2r,6s,13as,14ar,16as,z)-n-(cyclopropylsulfonyl)-6-(5-methylpyrazine-2-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxamide

    11. Abt 450

    12. Veruprevir [inn]

    13. Paritaprevir [usan]

    14. Paritaprevir [usan:inn]

    15. Unii-ou2ym37k86

    16. Paritaprevir [mi]

    17. Paritaprevir [inn]

    18. Paritaprevir [vandf]

    19. Veruprevir (deprecated Inn)

    20. Paritaprevir [who-dd]

    21. Schembl3069964

    22. Chembl3391662

    23. Gtpl11273

    24. Amy6938

    25. Dtxsid601027922

    26. Paritaprevir [orange Book]

    27. Paritaprevir(veruprevir Abt-450)

    28. (2r,6s,12z,13ar,14ar,16as)-n-(cyclopropanesulfonyl)-6-[(5-methylpyrazine-2-carbonyl)amino]-5,16-dioxo-2-[(phenanthridin-6-yl)oxy]-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5h)-carboxamide

    29. Ex-a2278

    30. S5404

    31. Viekirax Component Paritaprevir

    32. Akos025396424

    33. Zinc197964623

    34. Ccg-270449

    35. Cs-5051

    36. Db09297

    37. Ncgc00509859-02

    38. Paritaprevir Component Of Viekirax

    39. Ac-33061

    40. As-75348

    41. Hy-12594

    42. A857160

    43. (1s,4r,6s,7z,14s,18r)-n-(cyclopropanesulfonyl)-14-(5-methylpyrazine-2-amido)-2,15-dioxo-18-(phenanthridin-6-yloxy)-3,16-diazatricyclo[14.3.0.0?,?]nonadec-7-ene-4-carboxamide

    44. (1s,4r,6s,7z,14s,18r)-n-cyclopropylsulfonyl-14-[(5-methylpyrazine-2-carbonyl)amino]-2,15-dioxo-18-phenanthridin-6-yloxy-3,16-diazatricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxamide

    45. (2r,6s,12z,13as,14ar,16as)-n-(cyclopropylsulfonyl)-6-{[(5-methyl-2-pyrazinyl)carbonyl]amino}-5,16-dioxo-2-(6-phenanthridinyloxy)-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5h)-carboxamide

    46. (2r,6s,13as,14ar,16as,z)-n-(cyclopropylsulfonyl)-6-(5-methylpyrazine-2-carboxamido)-5,16-dioxo-2-(phenanthridin-6-yloxy)-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5h)-carboxamide

    47. Cyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a(5h)-carboxamide, N-(cyclopropylsulfonyl)-1,2,3,6,7,8,9,10,11,13a,14,15,16,16a-tetradecahydro-6-[[(5-methyl-2-pyrazinyl)carbonyl]amino]-5,16-dioxo-2-(6-phenanthridinyloxy)-, (2r,6s,12z,13as,14ar,16as)-

    2.4 Create Date
    2010-04-20
    3 Chemical and Physical Properties
    Molecular Weight 765.9 g/mol
    Molecular Formula C40H43N7O7S
    XLogP34.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count7
    Exact Mass765.29446791 g/mol
    Monoisotopic Mass765.29446791 g/mol
    Topological Polar Surface Area198 Ų
    Heavy Atom Count55
    Formal Charge0
    Complexity1600
    Isotope Atom Count0
    Defined Atom Stereocenter Count5
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    When used within the fixed-dose combination product with [DB09296], [DB09183], and [DB00503] as the FDA-approved product Viekira Pak, paritaprevir is indicated for the treatment of HCV genotype 1b without cirrhosis or with compensated cirrhosis, and when combined with [DB00811] for the treatment of HCV genotype 1a without cirrhosis or with compensated cirrhosis. When used within the fixed-dose combination product with [DB09296] and [DB00503] as the FDA- and Health Canada-approved product Technivie, paritaprevir is indicated in combination with [DB00811] for the treatment of patients with genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis or with compensated cirrhosis. When used within the fixed-dose combination product with [DB09296], [DB09183], and [DB00503] as the Health Canada-approved, commercially available product Holkira Pak, paritaprevir is indicated for the treatment of HCV genotype 1b with or without cirrhosis, and when combined with [DB00811] for the treatment of HCV genotype 1a with or without cirrhosis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    At concentrations approximately 6 and 1.8 times the therapeutic concentrations of paritaprevir and ombitasvir, the combination did not prolong QTc to any clinically relevant extent.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    PARITAPREVIR
    5.2.2 FDA UNII
    OU2YM37K86
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors
    5.3 Absorption, Distribution and Excretion

    Absorption

    Tmax of approximately 4 to 5 hours with a maximum concentration (Cmax) of 194 ng/mL.

    Route of Elimination

    Following a single dose administration of 14C-paritaprevir co-dosed with 100 mg of ritonavir, approximately 88% of the radioactivity was recovered in feces with limited radioactivity (8.8%) in urine; unchanged paritaprevir accounted for 1.1% of the radioactivity in the feces and 0.05% in the urine.

    Volume of Distribution

    Volume of distribution at steady state is approximately 103 L.

    5.4 Metabolism/Metabolites

    Paritaprevir is predominantly metabolized by CYP3A4 and to a lesser extent by CYP3A5.

    5.5 Biological Half-Life

    5.5 hr

    5.6 Mechanism of Action

    Paritaprevir is a potent inhibitor of the NS3/4A serine protease of Hepatitis C Virus (HCV). Following viral replication of HCV genetic material and translation into a single polypeptide, Nonstructural Protein 3 (NS3) and its activating cofactor Nonstructural Protein 4A (NS4A) are responsible for cleaving it into the following structural and nonstructural proteins required for assembly into mature virus: NS3, NS4A, NS4B, NS5A, and NS5B. By inhibiting viral protease NS3/4A, paritaprevir therefore prevents viral replication and function.