Find Voxilaprevir manufacturers, exporters & distributors on PharmaCompass

Voxilaprevir

DRL offers a portfolio of products & services, including APIs, CMO services, generics, biosimilars & differentiated formulations.

ACCESS ALL DATA
Browse all information
CHEMISTRY
Discover Molecule Insights

ACTIVE PHARMA INGREDIENTS

1 API Suppliers, 2 KDMF, 1 NDC API, 1 Listed Suppliers

1 API Suppliers
2 KDMF
1 NDC API
1 Listed Suppliers

INTERMEDIATES

26 Intermediates Suppliers

26 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

2 FDF Dossiers, 1 FDA Orange Book, 1 Canada

2 FDF Dossiers
1 FDA Orange Book
1 Canada

DIGITAL CONTENT

4 NEWS #PharmaBuzz

media
4 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 Annual Reports

globalSalesInformation
1 Annual Reports

MARKET PLACE

1 APIs

marketPlace
1 APIs

PATENTS & EXCLUSIVITIES

47 US Patents

patents
47 US Patents

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 0

MARKET PLACE

API

FDF

26INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

Annual Reports (USD Million)

257

Finished Drug Prices

0RELATED EXCIPIENT COMPANIES

0EXCIPIENTS BY APPLICATIONS

Chemistry

Click the arrow to open the dropdown

Click the button for full data set

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.

API SUPPLIERS