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Paritaprevir

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TABLET;ORAL - 12.5MG;75MG;50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET, EXTENDED RELEASE;ORAL - EQ 200MG BASE;8.33MG;50MG;33.33MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

TABLET;ORAL - 12.5MG;75MG;50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET, EXTENDED RELEASE;ORAL - EQ 200MG BASE;8.33MG;50MG;33.33MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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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

Paritaprevir

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 Formula	C₄₀H₄₃N₇O₇S
Molecular Weight	765.9 g/mol
XLogP3	4.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	7
Exact Mass	765.29446791 g/mol
Monoisotopic Mass	765.29446791 g/mol
Topological Polar Surface Area	198 Å²
Heavy Atom Count	55
Formal Charge	0
Complexity	1600
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.