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Voxilaprevir

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Also known as: 1535212-07-7, Gs9857, Gs-9857, (1r,18r,20r,24s,27s,28s)-24-tert-butyl-n-[(1r,2r)-2-(difluoromethyl)-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide, 0570f37359, Voxilaprevir [inn]

Molecular Formula

C₄₀H₅₂F₄N₆O₉S

Molecular Weight

868.9 g/mol

InChI Key

MZBLZLWXUBZHSL-FZNJKFJKSA-N

FDA UNII

0570F37359

Voxilaprevir is an orally bioavailable inhibitor of the hepatitis C virus (HCV) non-structural protein 3/non-structural protein 4A (NS3/NS4A) serine protease, with antiviral activity. Upon administration, voxilaprevir binds to the HCV NS3/NS4A serine 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, thereby preventing viral replication and function. 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; HCV infection is associated with the development of hepatocellular carcinoma (HCC).

Voxilaprevir is a Hepatitis C Virus NS3/4A Protease Inhibitor. The mechanism of action of voxilaprevir is as a HCV NS3/4A Protease Inhibitor, and P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor.

1 2D Structure

Voxilaprevir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,18R,20R,24S,27S,28S)-24-tert-butyl-N-[(1R,2R)-2-(difluoromethyl)-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide

2.1.2 InChI

InChI=1S/C40H52F4N6O9S/c1-7-22-27-19-50(28(22)32(51)48-39(18-23(39)31(41)42)35(53)49-60(55,56)38(5)14-15-38)34(52)30(37(2,3)4)47-36(54)59-26-16-20(26)10-8-9-13-40(43,44)29-33(58-27)46-25-17-21(57-6)11-12-24(25)45-29/h11-12,17,20,22-23,26-28,30-31H,7-10,13-16,18-19H2,1-6H3,(H,47,54)(H,48,51)(H,49,53)/t20-,22-,23+,26-,27+,28+,30-,39-/m1/s1

2.1.3 InChI Key

MZBLZLWXUBZHSL-FZNJKFJKSA-N

2.1.4 Canonical SMILES

CCC1C2CN(C1C(=O)NC3(CC3C(F)F)C(=O)NS(=O)(=O)C4(CC4)C)C(=O)C(NC(=O)OC5CC5CCCCC(C6=NC7=C(C=C(C=C7)OC)N=C6O2)(F)F)C(C)(C)C

2.1.5 Isomeric SMILES

CC[C@@H]1[C@@H]2CN([C@@H]1C(=O)N[C@@]3(C[C@H]3C(F)F)C(=O)NS(=O)(=O)C4(CC4)C)C(=O)[C@@H](NC(=O)O[C@@H]5C[C@H]5CCCCC(C6=NC7=C(C=C(C=C7)OC)N=C6O2)(F)F)C(C)(C)C

2.2 Other Identifiers

2.2.1 UNII

0570F37359

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Gs-9857

2.3.2 Depositor-Supplied Synonyms

1. 1535212-07-7

2. Gs9857

3. Gs-9857

4. (1r,18r,20r,24s,27s,28s)-24-tert-butyl-n-[(1r,2r)-2-(difluoromethyl)-1-[(1-methylcyclopropyl)sulfonylcarbamoyl]cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide

5. 0570f37359

6. Voxilaprevir [inn]

7. Voxilaprevir [usan:inn]

8. Unii-0570f37359

9. Voxilaprevir [mi]

10. Voxilaprevir (usan/inn)

11. Voxilaprevir [usan]

12. Voxilaprevir [who-dd]

13. C40h52f4n6o9s

14. Chembl4474855

15. Schembl15412621

16. Dtxsid301027947

17. Voxilaprevir [orange Book]

18. Ex-a5390

19. Vosevi Component Voxilaprevir

20. Db12026

21. Voxilaprevir Component Of Vosevi

22. Hy-19840

23. Cs-0017027

24. J3.665.048f

25. D10899

26. Q27236086

27. (1ar,5s,8s,9s,10r,22ar)-5-tert-butyl-n-[(1 R,2r)-2-(difluoromethyl)-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-9-ethyl-18,18-difluoro-14- Methoxy-3,6-dioxo-1,1a,3,4,5,6,9,1 0,18,19,20,21,22,22a-tetradecahydro-8h-7,10-methanocyclopropa[18,19]

28. 8h-7,10-methanocyclopropa(18,19)(1,10,3,6)dioxadiazacyclononadecino(11,12-b)quinoxaline-8-carboxamide, N-((1r,2r)-2-(difluoromethyl)-1-((((1-methylcyclopropyl)sulfonyl)amino)carbonyl)cyclopropyl)-5-(1,1-dimethylethyl)-9-ethyl-18,18-difluoro-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-14-methoxy-3,6-dioxo-, (1ar,5s,8s,9s,10r,22ar)-

29. L9p

2.4 Create Date

2015-02-13

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₅₂F₄N₆O₉S
Molecular Weight	868.9 g/mol
XLogP3	5.9
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	9
Exact Mass	868.34526108 g/mol
Monoisotopic Mass	868.34526108 g/mol
Topological Polar Surface Area	204 Å²
Heavy Atom Count	60
Formal Charge	0
Complexity	1780
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
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

Vosevi (Voxilaprevir/[DB08934]/[DB11613]) is approved for use in patients with genotypes 1-6 who have been previously treated with an NS5A inhibitor, or patients with genotypes 1a or 3 infection who have previously been treated with an HCV regimen containing [DB08934] without an NS5A inhibitor.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Voxilaprevir is a direct-acting antiviral agent that targets viral NS3/4A protein and causes a decrease in serum HCV RNA levels. It disrupts HCV replication by specifically inhibiting the critical functions of NS3/4A protein in the replication complex. It does not appear to prolong the QT interval even when given at 9 times the maximum recommended dose.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

VOXILAPREVIR

5.2.2 FDA UNII

0570F37359

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - Organic Anion Transporting Polypeptide 1B3 Inhibitors

5.3 Absorption, Distribution and Excretion

Absorption

When provided as the fixed dose combination product Vosevi with [DB08934] and [DB11613], voxilaprevir reaches a maximum concentration (Cmax) of 192 ng/mL at a maximum time (Tmax) of 4 hours post-dose.

Route of Elimination

Voxilaprevir is primarily eliminated via biliary excretion.

5.4 Metabolism/Metabolites

Voxilaprevir is primarily metabolized by Cytochrome P450 3A4 (CYP3A4) and to a lesser extent by CYP2C8 and CYP1A2.

5.5 Biological Half-Life

33 hr

5.6 Mechanism of Action

Voxilaprevir exerts its antiviral action by reversibley binding and inhibiting 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 genetic material 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, voxilaprevir therefore prevents viral replication and function.

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