Voxilaprevir
Identification
- Name
- Voxilaprevir
- Accession Number
- DB12026
- Description
Voxilaprevir is a Direct-Acting Antiviral (DAA) medication used as part of combination therapy to treat chronic Hepatitis C, an infectious liver disease caused by infection with Hepatitis C Virus (HCV). HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients 3.
Voxilaprevir exerts its antiviral action by reversibly binding and inhibiting the NS3/4A serine protease of Hepatitis C Virus (HCV) Label. 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 2. By inhibiting viral protease NS3/4A, voxilaprevir therefore prevents viral replication and function. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as voxilaprevir.
Voxilaprevir has been available since July 2017 in a fixed dose combination product with sofosbuvir and velpatasvir as the commercially available product Vosevi. Vosevi is approved for the treatment of adult patients with chronic HCV infection with genotype 1, 2, 3, 4, 5, or 6 infection Label. Notably, Vosevi 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 and have previously been treated with an HCV regimen containing sofosbuvir without an NS5A inhibitor 4. Prior to Vosevi, there were no approved retreatment options for patients who have previously received, and failed, a regimen containing an NS5A inhibitor for treatment of chronic HCV infection.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Voxilaprevir (DB12026)
- Weight
- Average: 868.94
Monoisotopic: 868.345261104 - Chemical Formula
- C40H52F4N6O9S
- Synonyms
- Voxilaprevir
- External IDs
- GS 9857
- GS-9857
- GS9857
Pharmacology
- Indication
Vosevi (Voxilaprevir/Sofosbuvir/Velpatasvir) 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 Sofosbuvir without an NS5A inhibitor 4.
- Associated Conditions
- Previously treated with an HCV regimen containing an NS5A inhibitor Chronic Hepatitis C Genotype 1
- Previously treated with an HCV regimen containing an NS5A inhibitor Chronic hepatitis C genotype 2
- Previously treated with an HCV regimen containing an NS5A inhibitor Chronic hepatitis C genotype 3
- Previously treated with an HCV regimen containing an NS5A inhibitor Chronic hepatitis C genotype 4
- Previously treated with an HCV regimen containing an NS5A inhibitor Chronic hepatitis C genotype 5
- Previously treated with an HCV regimen containing an NS5A inhibitor Chronic hepatitis C genotype 6
- Previously treated with an HCV regimen containing sofosbuvir without an NS5A inhibitor Chronic hepatitis C genotype 1a
- Previously treated with an HCV regimen containing sofosbuvir without an NS5A inhibitor Chronic hepatitis C genotype 3
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
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 Label.
- Mechanism of action
Voxilaprevir exerts its antiviral action by reversibley binding and inhibiting the NS3/4A serine protease of Hepatitis C Virus (HCV) Label. 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 2. By inhibiting viral protease NS3/4A, voxilaprevir therefore prevents viral replication and function.
Target Actions Organism ANS3/4A protein inhibitorHepatitis C Virus - Absorption
When provided as the fixed dose combination product Vosevi with Sofosbuvir and Velpatasvir, voxilaprevir reaches a maximum concentration (Cmax) of 192 ng/mL at a maximum time (Tmax) of 4 hours post-dose Label.
- Volume of distribution
- Not Available
- Protein binding
Voxilaprevir is more than 99% bound to human plasma proteins Label.
- Metabolism
Voxilaprevir is primarily metabolized by Cytochrome P450 3A4 (CYP3A4) and to a lesser extent by CYP2C8 and CYP1A2Label.
- Route of elimination
Voxilaprevir is primarily eliminated via biliary excretion Label.
- Half-life
33 hr Label
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Hepatitis C Virus
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Voxilaprevir can be increased when it is combined with Abametapir. Abatacept The metabolism of Voxilaprevir can be increased when combined with Abatacept. Abemaciclib Abemaciclib may decrease the excretion rate of Voxilaprevir which could result in a higher serum level. Abiraterone The serum concentration of Voxilaprevir can be increased when it is combined with Abiraterone. Acenocoumarol The metabolism of Voxilaprevir can be decreased when combined with Acenocoumarol. Acetaminophen The metabolism of Voxilaprevir can be decreased when combined with Acetaminophen. Acetylcysteine The excretion of Voxilaprevir can be decreased when combined with Acetylcysteine. Acyclovir The metabolism of Voxilaprevir can be decreased when combined with Acyclovir. Adalimumab The metabolism of Voxilaprevir can be increased when combined with Adalimumab. Adenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Voxilaprevir. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid St. John's Wort. This herb induces CYP3A metabolism and may reduce serum levels of voxilaprevir.
- Take separate from antacids. Take Vosevi (sofosbuvir, velpatasvir, and voxilaprevir) at least 4 hours before or after antacids. Antacids have been shown to reduce the serum levels of velpatasvir and may not impact voxilaprevir.
- Take with food.
Products
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Vosevi Voxilaprevir (100 mg) + Sofosbuvir (400 mg) + Velpatasvir (100 mg) Tablet Oral Gilead Sciences 2017-09-18 Not applicable Canada 
Vosevi Voxilaprevir (100 mg/1) + Sofosbuvir (400 mg/1) + Velpatasvir (100 mg/1) Tablet, film coated Oral Gilead Sciences, Inc. 2017-07-18 Not applicable US 
Categories
- ATC Codes
- J05AP56 — Sofosbuvir, velpatasvir and voxilaprevir
- Drug Categories
- Amides
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Antivirals for treatment of HCV infections
- BCRP/ABCG2 Inhibitors
- BCRP/ABCG2 Substrates
- Breast Cancer Resistance Protein Inhibitors
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Direct Acting Antivirals
- HCV NS3/4A Protease Inhibitors
- NS3/4A Protease Inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B1/SLCO1B1 Substrates
- OATP1B3 inhibitors
- OATP1B3 substrates
- Organic Anion Transporting Polypeptide 1B1 Inhibitors
- Organic Anion Transporting Polypeptide 1B3 Inhibitors
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Sulfones
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Cyclic peptides
- Alternative Parents
- Macrolactams / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Quinoxalines / Pyrrolidinecarboxamides / Anisoles / Alkyl aryl ethers / Pyrazines / Cyclopropanecarboxylic acids and derivatives / Tertiary carboxylic acid amides show 15 more
- Substituents
- Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Aminosulfonyl compound / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid show 34 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 0570F37359
- CAS number
- 1535212-07-7
- InChI Key
- MZBLZLWXUBZHSL-FZNJKFJKSA-N
- 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
- IUPAC Name
- (1R,18R,20R,24S,27S,28S)-24-tert-butyl-N-[(1R,2R)-2-(difluoromethyl)-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetraazapentacyclo[24.2.1.0^{3,12}.0^{5,10}.0^{18,20}]nonacosa-3(12),4,6,8,10-pentaene-27-carboxamide
- SMILES
- CC[[email protected]@H]1[[email protected]@H]2CN([[email protected]@H]1C(=O)N[[email protected]@]1(C[[email protected]]1C(F)F)C(=O)NS(=O)(=O)C1(C)CC1)C(=O)[[email protected]@H](NC(=O)O[[email protected]@H]1C[[email protected]]1CCCCC(F)(F)C1=C(O2)N=C2C=C(OC)C=CC2=N1)C(C)(C)C
References
- General References
- Bourliere M, Gordon SC, Flamm SL, Cooper CL, Ramji A, Tong M, Ravendhran N, Vierling JM, Tran TT, Pianko S, Bansal MB, de Ledinghen V, Hyland RH, Stamm LM, Dvory-Sobol H, Svarovskaia E, Zhang J, Huang KC, Subramanian GM, Brainard DM, McHutchison JG, Verna EC, Buggisch P, Landis CS, Younes ZH, Curry MP, Strasser SI, Schiff ER, Reddy KR, Manns MP, Kowdley KV, Zeuzem S: Sofosbuvir, Velpatasvir, and Voxilaprevir for Previously Treated HCV Infection. N Engl J Med. 2017 Jun 1;376(22):2134-2146. doi: 10.1056/NEJMoa1613512. [PubMed:28564569]
- Moradpour D, Penin F: Hepatitis C virus proteins: from structure to function. Curr Top Microbiol Immunol. 2013;369:113-42. doi: 10.1007/978-3-642-27340-7_5. [PubMed:23463199]
- American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
- FDA News Release: FDA approves Vosevi for Hepatitis C [Link]
- External Links
- PubChem Compound
- 89921642
- PubChem Substance
- 347828341
- ChemSpider
- 44209500
- 1939323
- ChEMBL
- CHEMBL3707372
- PDBe Ligand
- L9P
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Voxilaprevir
- PDB Entries
- 6nzt
- FDA label
- Download (1.34 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment HCV Coinfection / Human Immunodeficiency Virus (HIV) Infections / Liver Diseases 1 4 Completed Other Hepatitis C Viral Infection / Transplantation Disease Transmission 1 4 Recruiting Basic Science Cardiovascular Heart Disease / Hepatitis C Viral Infection / Human Immunodeficiency Virus (HIV) Infections 1 4 Recruiting Treatment Chronic Hepatitis C Virus (HCV) Infection 1 3 Active Not Recruiting Treatment Hepatitis C Virus Infection 1 3 Completed Treatment Hepatitis C Viral Infection 2 3 Completed Treatment Hepatitis C Virus Infection 3 2 Completed Treatment Chronic Hepatitis C Virus (HCV) Infection 2 2 Completed Treatment Hepatitis C Virus Infection 3 2 Terminated Treatment Hepatitis C Virus Infection 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet, film coated Oral Tablet, film coated Oral 400 MG Tablet, coated Oral 400 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS7964580 Yes 2011-06-21 2029-09-26 US US8334270 Yes 2012-12-18 2028-09-21 US US8633309 Yes 2014-01-21 2029-09-26 US US8618076 Yes 2013-12-31 2031-06-11 US US8735372 Yes 2014-05-27 2028-09-21 US US8580765 Yes 2013-11-12 2028-09-21 US US8889159 Yes 2014-11-18 2029-09-26 US US9085573 Yes 2015-07-21 2028-09-21 US US9284342 Yes 2016-03-15 2031-03-13 US US8940718 No 2015-01-27 2032-11-16 US US8575135 No 2013-11-05 2032-11-16 US US8921341 No 2014-12-30 2032-11-16 US US9585906 No 2017-03-07 2028-03-21 US US9296782 No 2016-03-29 2034-07-17 US US9868745 No 2018-01-16 2032-11-16 US Additional Data Available- Filed On
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0506 mg/mL ALOGPS logP 3.98 ALOGPS logP 4.9 ChemAxon logS -4.2 ALOGPS pKa (Strongest Acidic) 3.74 ChemAxon pKa (Strongest Basic) -0.84 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 10 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 195.22 Å2 ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 203.02 m3·mol-1 ChemAxon Polarizability 85.37 Å3 ChemAxon Number of Rings 7 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Hepatitis C Virus
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type peptidase activity
- Specific Function
- Not Available
- Gene Name
- NS3/4A
- Uniprot ID
- B0B3C9
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 72789.28 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- VOSEVI ( (sofosbuvir, velpatasvir, and voxilaprevir) FDA Label [File]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
Drug created on October 20, 2016 15:12 / Updated on June 12, 2020 11:42
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