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    Technical details about Voxilaprevir, learn more about the structure, uses, toxicity, action, side effects and more

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    Voxilaprevir

    APIs // Active Pharmaceutical Ingredients

    INTERMEDIATES

    DOSSIERs // Finished Dosage Forms

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    DIGITAL CONTENT

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    2D Structure
    Also known as: 1535212-07-7, Gs9857, Gs-9857, (1r,18r,20r,24s,27s,28s)-24-tert-butyl-n-[(1r,2r)-2-(difluoromethyl)-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide, 0570f37359, Voxilaprevir [inn]
    Molecular Formula
    C40H52F4N6O9S
    Molecular Weight
    868.9  g/mol
    InChI Key
    MZBLZLWXUBZHSL-FZNJKFJKSA-N
    FDA UNII
    0570F37359
    Voxilaprevir is an orally bioavailable inhibitor of the hepatitis C virus (HCV) non-structural protein 3/non-structural protein 4A (NS3/NS4A) serine protease, with antiviral activity. Upon administration, voxilaprevir binds to the HCV NS3/NS4A serine 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, thereby preventing viral replication and function. 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; HCV infection is associated with the development of hepatocellular carcinoma (HCC).
    Voxilaprevir is a Hepatitis C Virus NS3/4A Protease Inhibitor. The mechanism of action of voxilaprevir is as a HCV NS3/4A Protease Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1R,18R,20R,24S,27S,28S)-24-tert-butyl-N-[(1R,2R)-2-(difluoromethyl)-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide
    2.1.2 InChI
    InChI=1S/C40H52F4N6O9S/c1-7-22-27-19-50(28(22)32(51)48-39(18-23(39)31(41)42)35(53)49-60(55,56)38(5)14-15-38)34(52)30(37(2,3)4)47-36(54)59-26-16-20(26)10-8-9-13-40(43,44)29-33(58-27)46-25-17-21(57-6)11-12-24(25)45-29/h11-12,17,20,22-23,26-28,30-31H,7-10,13-16,18-19H2,1-6H3,(H,47,54)(H,48,51)(H,49,53)/t20-,22-,23+,26-,27+,28+,30-,39-/m1/s1
    2.1.3 InChI Key
    MZBLZLWXUBZHSL-FZNJKFJKSA-N
    2.1.4 Canonical SMILES
    CCC1C2CN(C1C(=O)NC3(CC3C(F)F)C(=O)NS(=O)(=O)C4(CC4)C)C(=O)C(NC(=O)OC5CC5CCCCC(C6=NC7=C(C=C(C=C7)OC)N=C6O2)(F)F)C(C)(C)C
    2.1.5 Isomeric SMILES
    CC[C@@H]1[C@@H]2CN([C@@H]1C(=O)N[C@@]3(C[C@H]3C(F)F)C(=O)NS(=O)(=O)C4(CC4)C)C(=O)[C@@H](NC(=O)O[C@@H]5C[C@H]5CCCCC(C6=NC7=C(C=C(C=C7)OC)N=C6O2)(F)F)C(C)(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    0570F37359
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gs-9857

    2.3.2 Depositor-Supplied Synonyms

    1. 1535212-07-7

    2. Gs9857

    3. Gs-9857

    4. (1r,18r,20r,24s,27s,28s)-24-tert-butyl-n-[(1r,2r)-2-(difluoromethyl)-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide

    5. 0570f37359

    6. Voxilaprevir [inn]

    7. Voxilaprevir [usan:inn]

    8. Unii-0570f37359

    9. Voxilaprevir [mi]

    10. Voxilaprevir (usan/inn)

    11. Voxilaprevir [usan]

    12. Voxilaprevir [who-dd]

    13. C40h52f4n6o9s

    14. Chembl4474855

    15. Schembl15412621

    16. Dtxsid301027947

    17. Voxilaprevir [orange Book]

    18. Ex-a5390

    19. Vosevi Component Voxilaprevir

    20. Db12026

    21. Voxilaprevir Component Of Vosevi

    22. Hy-19840

    23. Cs-0017027

    24. J3.665.048f

    25. D10899

    26. Q27236086

    27. (1ar,5s,8s,9s,10r,22ar)-5-tert-butyl-n-[(1 R,2r)-2-(difluoromethyl)-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-9-ethyl-18,18-difluoro-14- Methoxy-3,6-dioxo-1,1a,3,4,5,6,9,1 0,18,19,20,21,22,22a-tetradecahydro-8h-7,10-methanocyclopropa[18,19]

    28. 8h-7,10-methanocyclopropa(18,19)(1,10,3,6)dioxadiazacyclononadecino(11,12-b)quinoxaline-8-carboxamide, N-((1r,2r)-2-(difluoromethyl)-1-((((1-methylcyclopropyl)sulfonyl)amino)carbonyl)cyclopropyl)-5-(1,1-dimethylethyl)-9-ethyl-18,18-difluoro-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-14-methoxy-3,6-dioxo-, (1ar,5s,8s,9s,10r,22ar)-

    29. L9p

    2.4 Create Date
    2015-02-13
    3 Chemical and Physical Properties
    Molecular Weight 868.9 g/mol
    Molecular Formula C40H52F4N6O9S
    XLogP35.9
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count15
    Rotatable Bond Count9
    Exact Mass868.34526108 g/mol
    Monoisotopic Mass868.34526108 g/mol
    Topological Polar Surface Area204 Ų
    Heavy Atom Count60
    Formal Charge0
    Complexity1780
    Isotope Atom Count0
    Defined Atom Stereocenter Count8
    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

    Vosevi (Voxilaprevir/[DB08934]/[DB11613]) is approved for use in patients with genotypes 1-6 who have been previously treated with an NS5A inhibitor, or patients with genotypes 1a or 3 infection who have previously been treated with an HCV regimen containing [DB08934] without an NS5A inhibitor.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Voxilaprevir is a direct-acting antiviral agent that targets viral NS3/4A protein and causes a decrease in serum HCV RNA levels. It disrupts HCV replication by specifically inhibiting the critical functions of NS3/4A protein in the replication complex. It does not appear to prolong the QT interval even when given at 9 times the maximum recommended dose.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    VOXILAPREVIR
    5.2.2 FDA UNII
    0570F37359
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Organic Anion Transporting Polypeptide 1B3 Inhibitors
    5.3 Absorption, Distribution and Excretion

    Absorption

    When provided as the fixed dose combination product Vosevi with [DB08934] and [DB11613], voxilaprevir reaches a maximum concentration (Cmax) of 192 ng/mL at a maximum time (Tmax) of 4 hours post-dose.

    Route of Elimination

    Voxilaprevir is primarily eliminated via biliary excretion.

    5.4 Metabolism/Metabolites

    Voxilaprevir is primarily metabolized by Cytochrome P450 3A4 (CYP3A4) and to a lesser extent by CYP2C8 and CYP1A2.

    5.5 Biological Half-Life

    33 hr

    5.6 Mechanism of Action

    Voxilaprevir exerts its antiviral action by reversibley binding and inhibiting 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 genetic material 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, voxilaprevir therefore prevents viral replication and function.

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