Identification

Name
Dasabuvir
Accession Number
DB09183
Description

Dasabuvir is a direct acting antiviral 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 8. Treatment options for chronic Hepatitis C have advanced significantly since 2011, with the development of Direct Acting Antivirals (DAAs) such as Dasabuvir. Dasabuvir is a non-nucleoside NS5B inhibitor which binds to the palm domain of NS5B and induces a conformational change which renders the polymerase unable to elongate viral RNA Label. The binding sites for non-nucleoside NS5B inhibitors are poorly conserved across HCV genotypes leading to the restriction of Dasabuvir's use to genotype 1 only.

In a joint recommendation published in 2016, the American Association for the Study of Liver Diseases (AASLD) and the Infectious Diseases Society of America (IDSA) recommend Dasabuvir as first line therapy in combination with Ombitasvir, Paritaprevir, and Ritonavir for genotype 1b and with Ribavirin for genotype 1a of Hepatitis C 8. Dasabuvir, Ombitasvir, Paritaprevir, Ritonavir, and Ribavirin are used with the intent to cure, or achieve a sustained virologic response (SVR), after 12 weeks of therapy. SVR and eradication of HCV infection is associated with significant long-term health benefits including reduced liver-related damage, improved quality of life, reduced incidence of Hepatocellular Carcinoma, and reduced all-cause mortality 7.

Dasabuvir is available as a fixed dose combination product with Ombitasvir, Paritaprevir, and Ritonavir (tradename Viekira Pak) used for the treatment of chronic Hepatitis C. Approved in December 2014 by the FDA, Viekira Pak is indicated for the treatment of HCV genotype 1a with Ribavirin or genotype 1b without Ribavirin Label. When combined together, Dasabuvir Ombitasvir, Paritaprevir, and Ritonavir as the combination product Viekira Pak have been shown to achieve a SVR of 100% for genotype 1b and 89% or 95% for genotype 1a after 12 weeks or 24 weeks of treatment including Ribavirin.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 493.58
Monoisotopic: 493.167142155
Chemical Formula
C26H27N3O5S
Synonyms
  • Sodium 3-(3-tert-butyl-4-methoxy-5-{6­ [(methylsulfonyl)amino]naphthalene-2-yl}phenyl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-ide hydrate (1:1:1)
  • Dasabuvir
  • N-{6-[3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl]naphthalen-2-yl}methanesulfonamide
External IDs
  • ABT 333
  • ABT-333
  • ABT333

Pharmacology

Indication

Dasabuvir, in combination with Ombitasvir, Paritaprevir, and Ritonavir (as Viekira Pak) is indicated for the treatment of patients with HCV genotype 1a with Ribavirin or genotype 1b without Ribavirin including those with compensated cirrhosis Label.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Dasabuvir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotype 1 Label.

Mechanism of action

Dasabuvir is a non-nucleoside inhibitor of the HCV RNA-dependent RNA polymerase encoded by the NS5B gene, which is essential for replication of the viral genome Label. Based on drug resistance mapping studies of HCV genotypes 1a and 1b, dasabuvir targets the palm domain of the NS5B polymerase, and is therefore referred to as a non-nucleoside NS5B-palm polymerase inhibitor. The EC50 values of dasabuvir against genotype 1a-H77 and 1b-Con1 strains in HCV replicon cell culture assays were 7.7 nM and 1.8 nM, respectively.

By binding to NS5b outside of the active site of the enzyme, dasabuvir induces a conformational change thereby preventing further elongation of the nascent viral genome 6,Label. A limitation of binding outside of the active site is that these binding sites are poorly preserved across the viral genotypes. This results in a limited potential for cross-genotypic activity and increased potential for development of resistance. Dasabuvir is therefore limited to treating genotypes 1a and 1b, and must be used in combination with other antiviral products.

TargetActionsOrganism
ANonstructural protein 5B (NS5B)
inhibitor
Absorption

Dasabuvir reaches peak plasma concentration 4 hours after administration Label. The absolute bioavailability of Dasabuvir is 70%.

Volume of distribution

Dasabuvir has a volume of distribution at steady state of 149 liters Label.

Protein binding

Dasabuvir is greater than 99.5% bound to human plasma proteins Label.

Metabolism

Dasabuvir is predominantly metabolized by CYP2C8, and to a lesser extent by CYP3A Label.

Route of elimination

Dasabuvir is mainly excreted in the feces (94.4%) with very little excreted in the urine (2%) Label. 26.2% and 0.03% of the drug excreted in the feces and urine respectively was present as the parent compound suggesting metabolism as the major elimination pathway.

Half-life

The half-life of elimination of dasabuvir is 5.5 to 6 hours Label.

Clearance

Clearance of Dasabuvir has not been determined.

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

The most common adverse effects of Viekira Pak either in combination with or without Ribavirin were pruritus, nausea, insomnia, and asthenia Label.

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.
DrugInteraction
AbacavirThe metabolism of Abacavir can be decreased when combined with Dasabuvir.
AbametapirThe serum concentration of Dasabuvir can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Dasabuvir can be increased when combined with Abatacept.
AbemaciclibDasabuvir may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AbirateroneThe metabolism of Dasabuvir can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Dasabuvir can be decreased when combined with Acebutolol.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Dasabuvir.
AdalimumabThe metabolism of Dasabuvir can be increased when combined with Adalimumab.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Dasabuvir.
AfatinibThe serum concentration of Dasabuvir can be increased when it is combined with Afatinib.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid St. John's Wort. This herb induces the CYP3A metabolism of dasabuvir and may reduce its serum concentration. St. John's Wort is contraindicated for use with Viekira Pak.
  • Take at the same time every day.
  • Take with food.

Products

Product Ingredients
IngredientUNIICASInChI Key
Dasabuvir sodiumR2M8F5TK9T1132940-11-4XHGMJAKIIJSQMF-UHFFFAOYSA-M
Dasabuvir sodium monohydrateOG6D40M62L1456607-55-8SJHKKWUESHNTBB-UHFFFAOYSA-M
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ExvieraTablet, film coated250 mgOralAbbvie2015-01-15Not applicableEU flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Holkira PakDasabuvir (250 mg) + Ombitasvir (12.5 mg) + Paritaprevir (75 mg) + Ritonavir (50 mg)Kit; TabletOralAbbvie2015-01-062018-08-15Canada flag
Viekira PakDasabuvir sodium monohydrate (250 mg/1) + Ombitasvir heminonahydrate (12.5 mg/1) + Paritaprevir dihydrate (75 mg/1) + Ritonavir (50 mg/1)OralAbbVie Inc.2014-12-19Not applicableUS flag
Viekira XRDasabuvir sodium monohydrate (200 mg/1) + Ombitasvir heminonahydrate (8.33 mg/1) + Paritaprevir dihydrate (50 mg/1) + Ritonavir (33.33 mg/1)OralAbbVie Inc.2016-07-222019-01-17US flag

Categories

ATC Codes
J05AP09 — DasabuvirJ05AP52 — Dasabuvir, ombitasvir, paritaprevir and ritonavir
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylnaphthalenes. These are compounds containing a phenylnaphthalene skeleton, which consists of a naphthalene bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Phenylnaphthalenes
Direct Parent
Phenylnaphthalenes
Alternative Parents
Sulfanilides / Methoxyanilines / Phenylpropanes / Phenoxy compounds / Anisoles / Methoxybenzenes / Pyrimidones / Alkyl aryl ethers / Organosulfonamides / Organic sulfonamides
show 11 more
Substituents
Alkyl aryl ether / Aminosulfonyl compound / Anisole / Aromatic heteropolycyclic compound / Azacycle / Ether / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, sulfonamide, pyrimidone, ring assembly, naphthalenes (CHEBI:85182)

Chemical Identifiers

UNII
DE54EQW8T1
CAS number
1132935-63-7
InChI Key
NBRBXGKOEOGLOI-UHFFFAOYSA-N
InChI
InChI=1S/C26H27N3O5S/c1-26(2,3)22-15-20(29-11-10-23(30)27-25(29)31)14-21(24(22)34-4)18-7-6-17-13-19(28-35(5,32)33)9-8-16(17)12-18/h6-15,28H,1-5H3,(H,27,30,31)
IUPAC Name
N-{6-[3-tert-butyl-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl}methanesulfonamide
SMILES
COC1=C(C=C(C=C1C1=CC2=CC=C(NS(C)(=O)=O)C=C2C=C1)N1C=CC(=O)NC1=O)C(C)(C)C

References

General References
  1. Gentile I, Buonomo AR, Borgia G: Dasabuvir: A Non-Nucleoside Inhibitor of NS5B for the Treatment of Hepatitis C Virus Infection. Rev Recent Clin Trials. 2014;9(2):115-23. [PubMed:24882169]
  2. Trivella JP, Gutierrez J, Martin P: Dasabuvir : a new direct antiviral agent for the treatment of hepatitis C. Expert Opin Pharmacother. 2015 Mar;16(4):617-24. doi: 10.1517/14656566.2015.1012493. Epub 2015 Feb 9. [PubMed:25665437]
  3. Mantry PS, Pathak L: Dasabuvir (ABT333) for the treatment of chronic HCV genotype I: a new face of cure, an expert review. Expert Rev Anti Infect Ther. 2016 Feb;14(2):157-65. doi: 10.1586/14787210.2016.1120668. Epub 2015 Dec 17. [PubMed:26567871]
  4. McConachie SM, Wilhelm SM, Kale-Pradhan PB: New direct-acting antivirals in hepatitis C therapy: a review of sofosbuvir, ledipasvir, daclatasvir, simeprevir, paritaprevir, ombitasvir and dasabuvir. Expert Rev Clin Pharmacol. 2016 Feb;9(2):287-302. doi: 10.1586/17512433.2016.1129272. Epub 2016 Jan 8. [PubMed:26651915]
  5. Shen J, Serby M, Reed A, Lee AJ, Menon R, Zhang X, Marsh K, Wan X, Kavetskaia O, Fischer V: Metabolism and Disposition of Hepatitis C Polymerase Inhibitor Dasabuvir in Humans. Drug Metab Dispos. 2016 Aug;44(8):1139-47. doi: 10.1124/dmd.115.067512. Epub 2016 May 13. [PubMed:27179126]
  6. Bagaglio S, Uberti-Foppa C, Morsica G: Resistance Mechanisms in Hepatitis C Virus: implications for Direct-Acting Antiviral Use. Drugs. 2017 May 12. doi: 10.1007/s40265-017-0753-x. [PubMed:28497432]
  7. Myers RP, Shah H, Burak KW, Cooper C, Feld JJ: An update on the management of chronic hepatitis C: 2015 Consensus guidelines from the Canadian Association for the Study of the Liver. Can J Gastroenterol Hepatol. 2015 Jan-Feb;29(1):19-34. Epub 2015 Jan 13. [PubMed:25585348]
  8. American Association for the Study of Liver Diseases; Infectious Diseases Society of America. HCV guidance. http://hcvguidelines.org. Accessed June 12, 2017. [Link]
KEGG Drug
D10582
PubChem Compound
56640146
PubChem Substance
310265091
ChemSpider
29776744
RxNav
1597381
ChEBI
85182
ChEMBL
CHEMBL3137312
ZINC
ZINC000095616937
PharmGKB
PA166163411
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Dasabuvir
FDA label
Download (540 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection1
4Active Not RecruitingTreatmentChronic Hepatitis C Virus (HCV) Infection / Chronic Kidney Disease (CKD)1
4Active Not RecruitingTreatmentHepatitis C Virus (HCV) Infection1
4CompletedPreventionHepatitis C Viral Infection1
4CompletedTreatmentChronic Hepatitis C Virus (HCV) Infection1
4CompletedTreatmentHCV Coinfection1
4CompletedTreatmentHepatitis Viruses1
4Unknown StatusTreatmentChronic Hepatitis C Virus (HCV) Infection2
4Unknown StatusTreatmentChronic Hepatitis, C Virus1
3Active Not RecruitingTreatmentChronic Hepatitis C Genotype 12

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral250 mg
Tablet, coated250 mg
Kit; tabletOral
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US6703403Yes2004-03-092016-12-26US flag
US6037157Yes2000-03-142016-12-26US flag
US7364752Yes2008-04-292021-05-10US flag
US7148359Yes2006-12-122020-01-19US flag
US8268349Yes2012-09-182025-02-25US flag
US8399015Yes2013-03-192025-02-25US flag
US9139536No2015-09-222028-11-09US flag
US8685984No2014-04-012032-09-04US flag
US8466159No2013-06-182032-09-04US flag
US8642538No2014-02-042029-09-10US flag
US8501238No2013-08-062028-09-17US flag
US8680106No2014-03-252032-09-04US flag
US8492386No2013-07-232032-09-04US flag
US8188104No2012-05-292029-05-17US flag
US9006387No2015-04-142030-06-10US flag
US9044480No2015-06-022031-04-10US flag
US8686026No2014-04-012031-06-09US flag
US8420596Yes2013-04-162031-10-10US flag
US8691938No2014-04-082032-04-13US flag
US9629841No2017-04-252033-10-18US flag
US9333204No2016-05-102035-01-02US flag
US9744170No2017-08-292035-01-02US flag
US10105365No2018-10-232035-01-02US flag
US10201584No2019-02-122032-05-17US flag
US10201542No2019-02-122033-10-18US flag
US10201541No2019-02-122032-05-17US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000799 mg/mLALOGPS
logP4.7ALOGPS
logP3.42ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.81 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity134.04 m3·mol-1ChemAxon
Polarizability53.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Not Available
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
Rna binding
Gene Name
NS5b
Uniprot ID
P87764
Uniprot Name
Nonstructural protein 5b
Molecular Weight
Not Available
References
  1. Soriano V, Vispo E, de Mendoza C, Labarga P, Fernandez-Montero JV, Poveda E, Trevino A, Barreiro P: Hepatitis C therapy with HCV NS5B polymerase inhibitors. Expert Opin Pharmacother. 2013 Jun;14(9):1161-70. doi: 10.1517/14656566.2013.795543. Epub 2013 Apr 27. [PubMed:23621117]
  2. Mantry PS, Pathak L: Dasabuvir (ABT333) for the treatment of chronic HCV genotype I: a new face of cure, an expert review. Expert Rev Anti Infect Ther. 2016 Feb;14(2):157-65. doi: 10.1586/14787210.2016.1120668. Epub 2015 Dec 17. [PubMed:26567871]
  3. Trivella JP, Gutierrez J, Martin P: Dasabuvir : a new direct antiviral agent for the treatment of hepatitis C. Expert Opin Pharmacother. 2015 Mar;16(4):617-24. doi: 10.1517/14656566.2015.1012493. Epub 2015 Feb 9. [PubMed:25665437]

Enzymes

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
  1. Shen J, Serby M, Reed A, Lee AJ, Menon R, Zhang X, Marsh K, Wan X, Kavetskaia O, Fischer V: Metabolism and Disposition of Hepatitis C Polymerase Inhibitor Dasabuvir in Humans. Drug Metab Dispos. 2016 Aug;44(8):1139-47. doi: 10.1124/dmd.115.067512. Epub 2016 May 13. [PubMed:27179126]
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
References
  1. Shen J, Serby M, Reed A, Lee AJ, Menon R, Zhang X, Marsh K, Wan X, Kavetskaia O, Fischer V: Metabolism and Disposition of Hepatitis C Polymerase Inhibitor Dasabuvir in Humans. Drug Metab Dispos. 2016 Aug;44(8):1139-47. doi: 10.1124/dmd.115.067512. Epub 2016 May 13. [PubMed:27179126]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Shen J, Serby M, Reed A, Lee AJ, Menon R, Zhang X, Marsh K, Wan X, Kavetskaia O, Fischer V: Metabolism and Disposition of Hepatitis C Polymerase Inhibitor Dasabuvir in Humans. Drug Metab Dispos. 2016 Aug;44(8):1139-47. doi: 10.1124/dmd.115.067512. Epub 2016 May 13. [PubMed:27179126]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A4
Uniprot ID
P22310
Uniprot Name
UDP-glucuronosyltransferase 1-4
Molecular Weight
60024.535 Da

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
Substrate
General Function
Efflux transmembrane transporter activity
Specific Function
Drug efflux transporter present in a number of stem cells that acts as a regulator of cellular differentiation. Able to mediate efflux from cells of the rhodamine dye and of the therapeutic drug do...
Gene Name
ABCB5
Uniprot ID
Q2M3G0
Uniprot Name
ATP-binding cassette sub-family B member 5
Molecular Weight
138639.48 Da
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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

Drug created on October 15, 2015 12:45 / Updated on October 27, 2020 09:44

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