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    Pibrentasvir

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    2D Structure
    Also known as: 1353900-92-1, Abt-530, Pibrentasvir [usan], Abt 530, A-1325912.0, Abt530
    Molecular Formula
    C57H65F5N10O8
    Molecular Weight
    1113.2  g/mol
    InChI Key
    VJYSBPDEJWLKKJ-NLIMODCCSA-N
    FDA UNII
    2WU922TK3L
    Pibrentasvir is a direct acting antiviral agent and Hepatitis C virus (HCV) NS5A inhibitor that targets the the viral RNA replication and viron assembly. In combination with [DB13879], pibrentastiv is a useful therapy for patients who experienced therapeutic failure from other NS5A inhibitors. In cell cultures, the emergence of amino acid substitutions at known NS5A inhibitor resistance-associated positions in HCV genotype 1a, 2a or 3a replicons led to reduced susceptibility and resistance to pibrentasvir. These resistance-associated amino acid substitutions included Q30D/deletion, Y93D/H/N or H58D +Y93H in genotype 1a replicons, F28S + M31I or P29S + K30G in genotype 2a replicons, and Y93H in genotype 3a replicons. Individual NS5A amino acid substitutions that reduced susceptibility to pibrentasvir include M28G or Q30D in a genotype 1a replicon and P32-deletion in a genotype 1b replicon. Pibrentasvir is available as an oral combination therapy with [DB13879] under the brand name Mavyret. This fixed-dose combination therapy was FDA-approved in August 2017 to treat adults with chronic hepatitis C virus (HCV) genotypes 1-6 without cirrhosis (liver disease) or with mild cirrhosis, including patients with moderate to severe kidney disease and those who are on dialysis. Mavyret is also indicated for HCV genotype 1-infected patients who have been previously treated with regimens either containing an NS5A inhibitor or an NS3/4A protease inhibitor, but not both. Hepatitis C viral infection often leads to decreased liver function and subsequent liver failure, causing a significantly negative impact on the patients' quality of life. The ultimate goal of the combination treatment is to achieve sustained virologic response (SVR) and cure the patients from the infection. In clinical trials, this combination therapy achieved SVR12 rate, or undetectable Hepatitis C for twelve or more weeks after the end of treatment, of 93% across genotypes 1a, 2a, 3a, 4, 5 and 6.
    Pibrentasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of pibrentasvir is as a P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Cytochrome P450 3A Inhibitor, and Cytochrome P450 1A2 Inhibitor, and UGT1A1 Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl N-[(2S,3R)-1-[(2S)-2-[6-[(2R,5R)-1-[3,5-difluoro-4-[4-(4-fluorophenyl)piperidin-1-yl]phenyl]-5-[6-fluoro-2-[(2S)-1-[(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]pyrrolidin-2-yl]-5-fluoro-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-3-methoxy-1-oxobutan-2-yl]carbamate
    2.1.2 InChI
    InChI=1S/C57H65F5N10O8/c1-29(77-3)49(67-56(75)79-5)54(73)70-19-7-9-47(70)52-63-41-25-35(37(59)27-43(41)65-52)45-15-16-46(72(45)34-23-39(61)51(40(62)24-34)69-21-17-32(18-22-69)31-11-13-33(58)14-12-31)36-26-42-44(28-38(36)60)66-53(64-42)48-10-8-20-71(48)55(74)50(30(2)78-4)68-57(76)80-6/h11-14,23-30,32,45-50H,7-10,15-22H2,1-6H3,(H,63,65)(H,64,66)(H,67,75)(H,68,76)/t29-,30-,45-,46-,47+,48+,49+,50+/m1/s1
    2.1.3 InChI Key
    VJYSBPDEJWLKKJ-NLIMODCCSA-N
    2.1.4 Canonical SMILES
    CC(C(C(=O)N1CCCC1C2=NC3=C(N2)C=C(C(=C3)F)C4CCC(N4C5=CC(=C(C(=C5)F)N6CCC(CC6)C7=CC=C(C=C7)F)F)C8=CC9=C(C=C8F)N=C(N9)C1CCCN1C(=O)C(C(C)OC)NC(=O)OC)NC(=O)OC)OC
    2.1.5 Isomeric SMILES
    C[C@H]([C@@H](C(=O)N1CCC[C@H]1C2=NC3=C(N2)C=C(C(=C3)F)[C@H]4CC[C@@H](N4C5=CC(=C(C(=C5)F)N6CCC(CC6)C7=CC=C(C=C7)F)F)C8=CC9=C(C=C8F)N=C(N9)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)OC)NC(=O)OC)NC(=O)OC)OC
    2.2 Other Identifiers
    2.2.1 UNII
    2WU922TK3L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. A-1325912.0

    2. Abt-530

    3. Dimethyl N,n'-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)pyrrolidine-2,5-diyl)bis((6-fluoro-1h-benzimidazole-5,2-diyl)((2s)-pyrrolidine-2,1-diyl)((2s,3r)-3-methoxy-1-oxobutane-1,2-diyl)))biscarbamate

    2.3.2 Depositor-Supplied Synonyms

    1. 1353900-92-1

    2. Abt-530

    3. Pibrentasvir [usan]

    4. Abt 530

    5. A-1325912.0

    6. Abt530

    7. 2wu922tk3l

    8. 1353900-92-1 (free)

    9. Dimethyl N,n'-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)pyrrolidine-2,5-diyl)bis((6-fluoro-1h-benzimidazole-5,2-diyl)((2s)-pyrrolidine-2,1-diyl)((2s,3r)-3-methoxy-1-oxobutane-1,2-diyl)))biscarbamate

    10. Dimethyl ((2s,2's,3r,3'r)-((2s,2's)-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)pyrrolidine-2,5-diyl)bis(6-fluoro-1h-benzo[d]imidazole-5,2-diyl))bis(pyrrolidine-2,1-diyl))bis(3-methoxy-1-oxobutane-1,2-diyl))dicarbamate

    11. Methyl N-[(2s,3r)-1-[(2s)-2-[6-[(2r,5r)-1-[3,5-difluoro-4-[4-(4-fluorophenyl)piperidin-1-yl]phenyl]-5-[6-fluoro-2-[(2s)-1-[(2s,3r)-3-methoxy-2-(methoxycarbonylamino)butanoyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]pyrrolidin-2-yl]-5-fluoro-1h-benzimidazol-2-yl]pyrrolidin-1-yl]-3-methoxy-1-oxobutan-2-yl]carbamate

    12. Unii-2wu922tk3l

    13. Abt-530;pibrentasvir

    14. Pibrentasvir [mi]

    15. Pibrentasvir(abt-530)

    16. Pibrentasvir [inn]

    17. Pibrentasvir [jan]

    18. Pibrentasvir (abt-530)

    19. Pibrentasvir [who-dd]

    20. Pibrentasvir (jan/usan/inn)

    21. Schembl2756579

    22. Chembl3545123

    23. Schembl17639956

    24. Gtpl11268

    25. Ex-a865

    26. Dtxsid601027946

    27. Pibrentasvir [orange Book]

    28. C57h65f5n10o8

    29. Bdbm50453100

    30. Mavyret Component Pibrentasvir

    31. S9641

    32. Cs-8135

    33. Db13878

    34. Ac-33418

    35. Bs-15250

    36. J3.646.121g

    37. D10816

    38. J-690144

    39. Q47495788

    40. A 1325912.0

    41. Carbamic Acid, N,n'-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)-1-piperidinyl)phenyl)-2,5-pyrrolidinediyl)bis((6-fluoro-1h-benzimidazole-5,2-diyl)-(2s)-2,1-pyrrolidinediyl((1s)-1-((1r)-1-methoxyethyl)-2-oxo-2,1-ethanediyl)))bis-, C,c'-dimethyl Ester

    42. Methyl ((2s,3r)-1-((2s)-2-(5-((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)-5-(6-fluoro-2-((2s)-1-(n-(methoxycarbonyl)-o-methyl-l-threonyl)pyrrolidin-2-yl)-1h-benzimidazol-5-yl)pyrrolidin-2-yl)-6-fluoro-1h-benzimidazol-2-yl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-yl)carbamate

    2.4 Create Date
    2012-08-19
    3 Chemical and Physical Properties
    Molecular Weight 1113.2 g/mol
    Molecular Formula C57H65F5N10O8
    XLogP37.4
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count17
    Rotatable Bond Count17
    Exact Mass1112.49069988 g/mol
    Monoisotopic Mass1112.49069988 g/mol
    Topological Polar Surface Area200 Ų
    Heavy Atom Count80
    Formal Charge0
    Complexity2000
    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

    Indicated for the treatment of adult patients with chronic hepatitis C virus (HCV) genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh A). MAVYRET is also indicated for the treatment of adult patients with HCV genotype 1 infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor or an NS3/4A protease inhibitor (PI), but not both.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Pibrentasvir is a pan-genotypic . According to HCV replicon assays, pibrentasvir has EC50 values ranging from 0.08-4.6 nM agaisnt laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4d, 5a, and 6a, or EC50 values of 0.5-4.3 pM against laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4b, 4d, 5a, 6a, 6e and 6p. It is active against common resistance-conferring substitutions in HCV genotypes 1 to 6 that confers resistance and decreased therapeutic response from other NS5A inhibitors, inluding positions 24, 28, 30, 31, 58, 92, or 93 in NS5A. In a QT study, pibrentasvir is not shown to prolong the QTc interval.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    PIBRENTASVIR
    5.2.2 FDA UNII
    2WU922TK3L
    5.2.3 Pharmacological Classes
    Mechanisms of Action [MoA] - UGT1A1 Inhibitors
    5.3 Absorption, Distribution and Excretion

    Absorption

    In healthy subjects, the time it takes to reach the peak plasma concentration (Tmax) is approximately 5 hours. The mean peak plasma concentration (Cmax) is 110ng/mL in non-cirrhotic HCV-infected subjects. Relative to fasting conditions, the consumption of meals increases the absorption of pibrentasvir by 40-53%.

    Route of Elimination

    The predominant route of elimination of the drug is biliary-fecal, where 96.6% of administered drug is excreted in feces and 0% of the drug is excreted in the urine.

    5.4 Metabolism/Metabolites

    Pibrentasvir is not metabolized.

    5.5 Biological Half-Life

    The elimination half life (t1/2) is approximately 13 hours.

    5.6 Mechanism of Action

    NS5A is a phosphoprotein that plays an essential role in replication, assembly and maturation of infectious viral proteins. The basal phosphorylated form of NS5A, which is maintained by C-terminal serine cluster, is key in ensuring its interaction with the viral capsid protein, or the core protein. By blocking this interaction, pibrentasvir inhibits the assembly of proteins and production of mature HCV particles. NS5A also interacts with viral and cellular proteins to form the HCV replicase complex, and supports the RNA replication of HCV.