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Ombitasvir

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

TABLET;ORAL - 12.5MG;75MG;50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET, EXTENDED RELEASE;ORAL - EQ 200MG BASE;8.33MG;50MG;33.33MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

TABLET;ORAL - 12.5MG;75MG;50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**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RELEASE;ORAL - EQ 200MG BASE;8.33MG;50MG;33.33MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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2 Emulsifying Agents, 1 Surfactant & Foaming Agents, 1 Thickeners and Stabilizers, 1 Film Formers & Plasticizers, 1 Solubilizers, 1 Topical

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Also known as: 1258226-87-7, Abt-267, Ombitasvir(abt-267), Abt267, Chebi:85183, Abt 267

Molecular Formula

C₅₀H₆₇N₇O₈

Molecular Weight

894.1 g/mol

InChI Key

PIDFDZJZLOTZTM-KHVQSSSXSA-N

FDA UNII

2302768XJ8

Ombitasvir is an orally available inhibitor of the hepatitis C virus (HCV) non-structural protein 5A (NS5A) replication complex, with potential activity against HCV. Upon oral administration and after intracellular uptake, ombitasvir binds to and blocks the activity of the NS5A protein. This results in the disruption of the viral RNA replication complex, blockage of 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; HCV infection is associated with the development of hepatocellular carcinoma (HCC).

Ombitasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of ombitasvir is as an UGT1A1 Inhibitor.

1 2D Structure

Ombitasvir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl N-[(2S)-1-[(2S)-2-[[4-[(2S,5S)-1-(4-tert-butylphenyl)-5-[4-[[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

2.1.2 InChI

InChI=1S/C50H67N7O8/c1-30(2)42(53-48(62)64-8)46(60)55-28-10-12-40(55)44(58)51-35-20-14-32(15-21-35)38-26-27-39(57(38)37-24-18-34(19-25-37)50(5,6)7)33-16-22-36(23-17-33)52-45(59)41-13-11-29-56(41)47(61)43(31(3)4)54-49(63)65-9/h14-25,30-31,38-43H,10-13,26-29H2,1-9H3,(H,51,58)(H,52,59)(H,53,62)(H,54,63)/t38-,39-,40-,41-,42-,43-/m0/s1

2.1.3 InChI Key

PIDFDZJZLOTZTM-KHVQSSSXSA-N

2.1.4 Canonical SMILES

CC(C)C(C(=O)N1CCCC1C(=O)NC2=CC=C(C=C2)C3CCC(N3C4=CC=C(C=C4)C(C)(C)C)C5=CC=C(C=C5)NC(=O)C6CCCN6C(=O)C(C(C)C)NC(=O)OC)NC(=O)OC

2.1.5 Isomeric SMILES

CC(C)[C@@H](C(=O)N1CCC[C@H]1C(=O)NC2=CC=C(C=C2)[C@@H]3CC[C@H](N3C4=CC=C(C=C4)C(C)(C)C)C5=CC=C(C=C5)NC(=O)[C@@H]6CCCN6C(=O)[C@H](C(C)C)NC(=O)OC)NC(=O)OC

2.2 Other Identifiers

2.2.1 UNII

2302768XJ8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Abt-267

2. Abt267

3. N,n'-(((2s,5s)-1-(4-(1,1-dimethylethyl)phenyl)-2,5-pyrrolidinediyl)bis(4,1-phenyleneiminocarbonyl-(2s)-2,1-pyrrolidinediyl((1s)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl)))bis-c,c'-dimethyl Ester Carbamic Acid

2.3.2 Depositor-Supplied Synonyms

1. 1258226-87-7

2. Abt-267

3. Ombitasvir(abt-267)

4. Abt267

5. Chebi:85183

6. Abt 267

7. Ombitasvir (usan)

8. Ombitasvir [usan]

9. 2302768xj8

10. Carbamic Acid, N,n'-(((2s,5s)-1-(4-(1,1-dimethylethyl)phenyl)-2,5-pyrrolidinediyl)bis(4,1-phenyleneiminocarbonyl-(2s)-2,1-pyrrolidinediyl((1s)-1-(1-methylethyl)-2-oxo-2,1-ethanediyl)))bis-, C,c'-dimethyl Ester

11. L-prolinamide, 2,2'-[[(2s,5s)-1-[4-(1,1-dimethylethyl)phenyl]-2,5-pyrrolidinediyl]di-4,1-phenylene]bis[n-(methoxycarbonyl)-l-valyl-

12. L-prolinamide,2,2'-(((2s,5s)-1-(4-(1,1-dimethylethyl)phenyl)-2,5-pyrrolidinediyl)di-4,1-phenylene)bis(n-(methoxycarbonyl)-l-valyl-

13. Dimethyl ([(2s,5s)-1-(4-tert-butylphenyl)pyrrolidine-2,5-diyl]bis{(4,1-phenylene)carbamoyl(2s)pyrrolidine-2,1-diyl[(2s)-3-methyl-1-oxobutane-1,2-diyl]})biscarbamate

14. Methyl N-[(2s)-1-[(2s)-2-[[4-[(2s,5s)-1-(4-tert-butylphenyl)-5-[4-[[(2s)-1-[(2s)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate

15. Ombitasvir [inn]

16. Ombitasvir [usan:inn]

17. Unii-2302768xj8

18. Ombitasvir [mi]

19. Ombitasvir [vandf]

20. Ombitasvir [who-dd]

21. Schembl8542284

22. Chembl3127326

23. Ombitasvir [orange Book]

24. Gtpl11272

25. Amy6935

26. Dtxsid201027920

27. Ex-a5846

28. Viekirax Component Ombitasvir

29. Bdbm50453112

30. S5403

31. Zinc150601177

32. Ccg-270561

33. Cs-5330

34. Db09296

35. Ombitasvir Component Of Viekirax

36. Abt-267;abt267;abt 267

37. Compound 38 [pmid: 24400777]

38. Ncgc00510316-01

39. Ncgc00510316-02

40. Hy-13997

41. C72037

42. D10576

43. Technivie (ombitasvir + Paritaprevir + Ritonavir)

44. Q19598175

45. Methyl ((s)-1-((s)-2-((4-((2s,5s)-1-(4-(tert-butyl)phenyl)-5-(4-((s)-1-((methoxycarbonyl)-l-valyl)pyrrolidine-2-carboxamido)phenyl)pyrrolidin-2-yl)phenyl)carbamoyl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamate

46. Methyl N-[(1s)-1-[(2s)-2-[[4-[(2s,5s)-1-(4-tert-butylphenyl)-5-[4-[[(2s)-1-[(2s)-2-(methoxycarbonylamino)-3-methyl-butanoyl]pyrrolidine-2-carbonyl]amino]phenyl]pyrrolidin-2-yl]phenyl]carbamoyl]pyrrolidine-1-carbonyl]-2-methyl-propyl]carbamate

2.4 Create Date

2012-01-23

3 Chemical and Physical Properties

Molecular Formula	C₅₀H₆₇N₇O₈
Molecular Weight	894.1 g/mol
XLogP3	7.9
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	16
Exact Mass	893.50511212 g/mol
Monoisotopic Mass	893.50511212 g/mol
Topological Polar Surface Area	179 Å²
Heavy Atom Count	65
Formal Charge	0
Complexity	1540
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 Indication

When used in combination with [DB09297] and [DB00503] (as the fixed dose product Technivie), Ombitasvir is indicated in combination with [DB00811] for the treatment of patients with genotype 4 chronic hepatitis C virus (HCV) infection without cirrhosis. When used in combination with [DB09297], [DB00503], and [DB09183] (as the fixed dose product Viekira Pak), Ombitasvir is indicated for the treatment of HCV genotype 1b and ,when combined with [DB00811], for the treatment of HCV genotype 1a

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Ombitasvir is classified as a direct acting antiviral and acts against HCV to inhibit viral replication.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

OMBITASVIR

5.2.2 FDA UNII

2302768XJ8

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - UGT1A1 Inhibitors

5.3 Absorption, Distribution and Excretion

Absorption

Ombitasvir reaches peak plasma concentration 5 hours after administration. It has an absolute bioavailability of 48%. Taking ombitasvir with high or normal fat meals increases exposure by 1.76 or 1.82 fold respectively.

Route of Elimination

Ombitasvir is mainly excreted in the feces (90.2%) with very little excreted in the urine (1.91%). 87.8% and 0.03% of the dose excreted in the feces and urine respectively is present as the parent compound.

Volume of Distribution

Ombitasvir has a volume of distribution at steady state of 173 liters.

Clearance

Clearance of Ombitasvir has not been determined.

5.4 Metabolism/Metabolites

Ombitasvir is mainly metabolized by amide hydrolysis followed by CYP2C8-mediated oxidative metabolism.

5.5 Biological Half-Life

Ombitasvir has a half life of elimination of 21-25 hours

5.6 Mechanism of Action

Ombitasvir is an inhibitor of the HCV non-structural protein 5A. While the precise role of this protein is unknown, it is essential to viral replication and virion assembly. Potential modes of action of NS5A inhibitors like Elbasvir include blocking signaling interactions, redistribution of NS5A from the endoplasmic reticulum to the surface of lipid droplets, and modification of the HCV replication complex.