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    Chemistry

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    Also known as: 1377049-84-7, Gs-5816, Gs5816, Kcu0c7rs7z, Gs 5816, Methyl ((r)-2-((2s,4s)-2-(5-(2-((2s,5s)-1-((methoxycarbonyl)-l-valyl)-5-methylpyrrolidin-2-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate
    Molecular Formula
    C49H54N8O8
    Molecular Weight
    883.0  g/mol
    InChI Key
    FHCUMDQMBHQXKK-CDIODLITSA-N
    FDA UNII
    KCU0C7RS7Z
    Velpatasvir
    Velpatasvir is an orally available inhibitor of the hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex, with potential activity against HCV genotypes 1-6. Although the exact mechanism of action of velpatasvir has not yet been completely determined, upon oral administration and intracellular uptake, it appears to bind to domain I of the NS5A protein. This inhibits the activity of the NS5A protein and results in the disruption of the viral RNA replication complex, blockage of viral 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.
    Velpatasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of velpatasvir is as a Breast Cancer Resistance Protein Inhibitor, and P-Glycoprotein Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Organic Anion Transporting Polypeptide 2B1 Inhibitor.
    1 2D Structure

    Velpatasvir

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    methyl N-[(1R)-2-[(2S,4S)-2-[5-[6-[(2S,5S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),5,9,11,14(19),15,17-nonaen-17-yl]-1H-imidazol-2-yl]-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate
    2.1.2 InChI
    InChI=1S/C49H54N8O8/c1-26(2)41(54-48(60)63-5)47(59)57-27(3)12-17-38(57)45-51-36-16-14-30-20-35-33-15-13-31(19-32(33)25-65-40(35)21-34(30)43(36)53-45)37-22-50-44(52-37)39-18-28(24-62-4)23-56(39)46(58)42(55-49(61)64-6)29-10-8-7-9-11-29/h7-11,13-16,19-22,26-28,38-39,41-42H,12,17-18,23-25H2,1-6H3,(H,50,52)(H,51,53)(H,54,60)(H,55,61)/t27-,28-,38-,39-,41-,42+/m0/s1
    2.1.3 InChI Key
    FHCUMDQMBHQXKK-CDIODLITSA-N
    2.1.4 Canonical SMILES
    CC1CCC(N1C(=O)C(C(C)C)NC(=O)OC)C2=NC3=C(N2)C=CC4=CC5=C(C=C43)OCC6=C5C=CC(=C6)C7=CN=C(N7)C8CC(CN8C(=O)C(C9=CC=CC=C9)NC(=O)OC)COC
    2.1.5 Isomeric SMILES
    C[C@H]1CC[C@H](N1C(=O)[C@H](C(C)C)NC(=O)OC)C2=NC3=C(N2)C=CC4=CC5=C(C=C43)OCC6=C5C=CC(=C6)C7=CN=C(N7)[C@@H]8C[C@@H](CN8C(=O)[C@@H](C9=CC=CC=C9)NC(=O)OC)COC
    2.2 Other Identifiers
    2.2.1 UNII
    KCU0C7RS7Z
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Gs-5816

    2.3.2 Depositor-Supplied Synonyms

    1. 1377049-84-7

    2. Gs-5816

    3. Gs5816

    4. Kcu0c7rs7z

    5. Gs 5816

    6. Methyl ((r)-2-((2s,4s)-2-(5-(2-((2s,5s)-1-((methoxycarbonyl)-l-valyl)-5-methylpyrrolidin-2-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-9-yl)-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate

    7. Methyl [(2s)-1-[(2s,5s)-2-[9-[2-[(2s,4s)-1-[(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl]-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-5-yl]-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl]-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

    8. Methyl N-[(1r)-2-[(2s,4s)-2-[5-[6-[(2s,5s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.03,11.04,8.014,19]henicosa-1(13),2,4(8),5,9,11,14(19),15,17-nonaen-17-yl]-1h-imidazol-2-yl]-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate

    9. Unii-kcu0c7rs7z

    10. Velpatasvir [usan:inn]

    11. Verpatasvir

    12. Methyl ((2s)-1-((2s,5s)-2-(9-(2-((2s,4s)-1-((2r)-2-((methoxycarbonyl)amino)-2-phenylacetyl)-4-(methoxymethyl)pyrrolidin-2-yl)-1h-imidazol-5-yl)-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate

    13. Methyl {(2s)-1-[(2s,5s)-2-(9-{2-[(2s,4s)-1-{(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-5-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

    14. Velpatasvir [inn]

    15. Velpatasvir(gs5816)

    16. Velpatasvir [mi]

    17. Velpatasvir [jan]

    18. Velpatasvir; Gs-5816

    19. Velpatasvir [usan]

    20. Velpatasvir [who-dd]

    21. Velpatasvir (jan/usan/inn)

    22. Schembl8756902

    23. Chembl3545062

    24. Schembl19236068

    25. Gtpl11269

    26. Amy4211

    27. Dtxsid70722565

    28. Velpatasvir [orange Book]

    29. Chebi:133009

    30. Epclusa (sofosbuvir + Velpatasvir)

    31. Vosevi Component Velpatasvir

    32. Bcp13813

    33. Epclusa Component Velpatasvir

    34. Ex-a2320

    35. Bdbm50521720

    36. Mfcd28411371

    37. S3724

    38. Velpatasvir Component Of Vosevi

    39. Zinc203686879

    40. Ccg-270553

    41. Cs-5977

    42. Db11613

    43. Velpatasvir Component Of Epclusa

    44. Ncgc00522503-01

    45. Ncgc00522503-02

    46. Ac-28744

    47. As-35237

    48. Hy-12530

    49. Ft-0700879

    50. J3.631.686a

    51. D10806

    52. Gs-5816;gs5816;gs 5816

    53. Vosevi (sofosbuvir + Velpatasvir + Voxilaprevi)

    54. A886410

    55. Q25018296

    56. Carbamic Acid, N-[(1r)-2-[(2s,4s)-2-[5-[1,11-dihydro-2-[(2s,5s)-1-[(2s)-2-[(methoxycarbonyl)amino]-3-methyl-1-oxobutyl]-5-methyl-2-pyrrolidinyl][2]benzopyrano[4,3:6,7]naphth[1,2-d]imidazol-9-yl]-1h-imidazol-2-yl]-4-(methoxymethyl)-1-pyrrolidinyl]-2-oxo-1-phenylethyl]-, Methyl Ester

    57. Methyl {(2s)-1-[(2s,5s)-2-(9-{2-[(2s,4s)-1-{(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-4-yl}-1,11-dihydro[2]benzopyrano[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

    58. Methyl N-[(1r)-2-[(2s,4s)-2-(5-{6-[(2s,5s)-1-[(2s)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.0?,??.0?,?.0??,??]henicosa-1,3,6,8,10,12,14,16,18-nonaen-17-yl}-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate

    59. Methyl N-[(1r)-2-[(2s,4s)-2-(5-{6-[(2s,5s)-1-[(2s)-2-[(methoxycarbonyl)amino]-3-methylbutanoyl]-5-methylpyrrolidin-2-yl]-21-oxa-5,7-diazapentacyclo[11.8.0.03,11.0?,?.01?,1?]henicosa-1,3,6,8,10,12,14,16,18-nonaen-17-yl}-1h-imidazol-2-yl)-4-(methoxymethyl)pyrrolidin-1-yl]-2-oxo-1-phenylethyl]carbamate

    60. Methyl{(2s)-1-[(2s,5s)-2-(9-{2-[(2s,4s)-1-{(2r)-2-[(methoxycarbonyl)amino]-2-phenylacetyl}-4-(methoxymethyl)pyrrolidin-2-yl]-1h-imidazol-5-yl}-1,11-dihydroisochromeno[4',3':6,7]naphtho[1,2-d]imidazol-2-yl)-5-methylpyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}carbamate

    2.4 Create Date
    2012-11-30
    3 Chemical and Physical Properties
    Molecular Weight 883.0 g/mol
    Molecular Formula C49H54N8O8
    XLogP36.2
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count13
    Exact Mass882.40646071 g/mol
    Monoisotopic Mass882.40646071 g/mol
    Topological Polar Surface Area193 Ų
    Heavy Atom Count65
    Formal Charge0
    Complexity1690
    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 Information
    1 of 2  
    Drug NameEPCLUSA
    Active IngredientSOFOSBUVIR; VELPATASVIR
    CompanyGILEAD SCIENCES INC (Application Number: N208341. Patents: 7964580, 8334270, 8575135, 8580765, 8618076, 8633309, 8735372, 8889159, 8921341, 8940718, 9085573, 9284342, 9757406)

    2 of 2  
    Drug NameVOSEVI
    Active IngredientSOFOSBUVIR; VELPATASVIR; VOXILAPREVIR
    CompanyGILEAD SCIENCES INC (Application Number: N209195. Patents: 7964580, 8334270, 8575135, 8580765, 8618076, 8633309, 8735372, 8889159, 8921341, 8940718, 9085573, 9284342, 9296782, 9585906)

    4.2 Drug Indication

    Velpatasvir is used in combination therapy with other antiviral medications to treat chronic hepatitis C virus (HCV) infected patients with HCV genoptypes 1-6, and to treat HCV and HIV co-infected patients. Depending on the level of cirrhosis or decompensation, combination therapy can also include therapy with [DB00811]. When used in combination with [DB08934] as the combination product Epclusa, Velpatasvir is 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, or in combination with [DB00811] if associated with decompensated cirrhosis.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Velpatasvir is a small molecule direct-acting antiviral used in the treatment of hepatitis C in combination with sofosbuvir. Velpatasvir prevents viral replication by inhibiting non-structural protein 5A (NS5A). At a dose 5 times the recommended dose, velpatasvir 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
    VELPATASVIR
    5.3.2 FDA UNII
    KCU0C7RS7Z
    5.3.3 Pharmacological Classes
    Mechanisms of Action [MoA] - Organic Anion Transporting Polypeptide 2B1 Inhibitors
    5.4 Absorption, Distribution and Excretion

    Absorption

    Oral bioavailability of 25-30%.

    Route of Elimination

    94% excreted in feces with 77% as parent compound. 0.4% excreted in urine.

    Volume of Distribution

    1.4-1.6 L/kg.

    Clearance

    Estimated 0.12 L/h/kg [A19175.

    5.5 Metabolism/Metabolites

    Some metabolism by CYP2B6, CYP2C8, and CYP3A4.

    5.6 Biological Half-Life

    15h.

    5.7 Mechanism of Action

    Velpatasvir's mechanism of action is likely similar to other selective NS5A inhibitors which bind domain I of NS5A consisting of amino acids 33-202. NS5A inhibitors compete with RNA for binding at this site. It is also thought that NS5A inhibitors bind the target during its action in replication when the binding site is exposed. Inhibition of NS5A is also known to produce redistribution of the protein to lipid droplets. The exact role of NS5A in RNA replication is not yet understood although it is known to be an important component.

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    API Reference Price

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QUANZHOU FORTUNE BIOPHARMA CO.LTD","supplierCountry":"CHINA","foreign_port":"BEIJING","customer":"KWALITY PHARMACEUTICALS","customerCountry":"INDIA","quantity":"2.00","actualQuantity":"2","unit":"KGS","unitRateFc":"3300","totalValueFC":"6667.8","currency":"USD","unitRateINR":"278685","date":"06-Jul-2024","totalValueINR":"557370","totalValueInUsd":"6667.8","indian_port":"Delhi Air","hs_no":"29339990","bill_no":"4356231","productDescription":"API","marketType":"REGULATED MARKET","country":"CHINA","selfForZScoreResived":"Pharma Grade","supplierPort":"BEIJING","supplierAddress":"ADD:ROOM2603,RONG TAI\\'AN BUILDING,NO.139 JINHUAI STREET,FENGZE ROAD,FENGZE DISTRICT, QUANZHOU CITY,FUJI CHINA","customerAddress":"VILLAGE NAG KALAN,MAJITHA ROAD,MAJ"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1721845800,"product":"VELPATASVIR BATCH NO. : VLP-702-240401","address":"A-202, 2ND FLOOR, MONDEAL SQUARE","city":"S.G. 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    26-Jun-2021
    30-Sep-2024
    KGS
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