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CAS 1377049-84-7

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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 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

CAS 1377049-84-7

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 Formula	C₄₉H₅₄N₈O₈
Molecular Weight	883.0 g/mol
XLogP3	6.2
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	13
Exact Mass	882.40646071 g/mol
Monoisotopic Mass	882.40646071 g/mol
Topological Polar Surface Area	193 Å²
Heavy Atom Count	65
Formal Charge	0
Complexity	1690
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	EPCLUSA
Active Ingredient	SOFOSBUVIR; VELPATASVIR
Company	GILEAD SCIENCES INC (Application Number: N208341. Patents: 7964580, 8334270, 8575135, 8580765, 8618076, 8633309, 8735372, 8889159, 8921341, 8940718, 9085573, 9284342, 9757406)

2 of 2
Drug Name	VOSEVI
Active Ingredient	SOFOSBUVIR; VELPATASVIR; VOXILAPREVIR
Company	GILEAD SCIENCES INC (Application Number: N209195. Patents: 7964580, 8334270, 8575135, 8580765, 8618076, 8633309, 8735372, 8889159, 8921341, 8940718, 9085573, 9284342, 9296782, 9585906, 9868745)

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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