dasabuvir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antivirals RNA polymerase (NS5B) inhibitors 4914 1132935-63-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dasabuvir sodium monohydrate
  • dasabuvir
  • dasabuvir sodium
  • exviera
  • ABT-333
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. In a biochemical assay, dasabuvir inhibited a panel of genotype 1a and 1b NS5B polymerases. 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.
  • Molecular weight: 493.58
  • Formula: C26H27N3O5S
  • CLOGP: 4.07
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 2
  • TPSA: 104.81
  • ALOGS: -5.79
  • ROTB: 5

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.50 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Hosey CM, Chan R, Benet LZ
Vd (Volume of distribution) 2.13 L/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.01 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 5.70 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 20, 2014 EMA AbbVie Ltd
Dec. 19, 2014 FDA ABBVIE INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Jaundice 520.98 24.50 188 7704 30125 53311049
Blood bilirubin increased 378.78 24.50 156 7736 35574 53305600
Hyperbilirubinaemia 363.65 24.50 112 7780 10957 53330217
Hepatic failure 279.54 24.50 126 7766 35680 53305494
Ascites 215.85 24.50 109 7783 39626 53301548
Hepatic encephalopathy 151.82 24.50 58 7834 10801 53330373
Hepatocellular carcinoma 144.05 24.50 41 7851 3039 53338135
Hepatic cirrhosis 132.83 24.50 61 7831 17961 53323213
Asthenia 99.51 24.50 180 7712 343410 52997764
Anaemia 95.85 24.50 157 7735 276561 53064613
Vomiting 87.23 24.50 212 7680 496927 52844247
Nausea 85.97 24.50 275 7617 755816 52585358
Drug ineffective 75.31 24.50 15 7877 817230 52523944
Haemoglobin decreased 66.10 24.50 91 7801 137216 53203958
Pruritus 63.14 24.50 136 7756 293696 53047478
Yellow skin 62.66 24.50 20 7872 2186 53338988
Child-Pugh-Turcotte score increased 61.34 24.50 10 7882 44 53341130
Ocular icterus 58.83 24.50 22 7870 3857 53337317
Bilirubin conjugated increased 58.33 24.50 20 7872 2731 53338443
Renal impairment 57.26 24.50 66 7826 83252 53257922
Chromaturia 51.25 24.50 31 7861 15919 53325255
Hepatorenal syndrome 43.87 24.50 15 7877 2030 53339144
Encephalopathy 43.30 24.50 39 7853 36769 53304405
Decreased appetite 42.13 24.50 96 7796 214878 53126296
Varices oesophageal 41.76 24.50 16 7876 2996 53338178
Off label use 40.65 24.50 10 7882 472202 52868972
Portal vein thrombosis 40.25 24.50 15 7877 2604 53338570
Fatigue 38.93 24.50 211 7681 730295 52610879
Oesophageal varices haemorrhage 38.24 24.50 12 7880 1241 53339933
Upper gastrointestinal haemorrhage 36.70 24.50 26 7866 17404 53323770
Acute hepatic failure 33.04 24.50 24 7868 16696 53324478
Hepatic cancer 32.69 24.50 14 7878 3487 53337687
Renal failure 31.49 24.50 60 7832 118392 53222782
Pain 31.10 24.50 25 7867 588373 52752801
Blood bilirubin unconjugated increased 30.78 24.50 8 7884 420 53340754
Insomnia 30.66 24.50 78 7814 186994 53154180
Hepatitis C 29.96 24.50 16 7876 6485 53334689

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Blood bilirubin increased 346.03 22.82 180 8500 38604 32466242
Jaundice 247.01 22.82 138 8542 34020 32470826
Ascites 226.15 22.82 138 8542 40053 32464793
Hepatocellular carcinoma 203.17 22.82 83 8597 10187 32494659
Hepatic failure 191.71 22.82 119 8561 35561 32469285
Hepatic cirrhosis 190.82 22.82 92 8588 16717 32488129
Hyperbilirubinaemia 154.10 22.82 81 8599 17649 32487197
Hepatic encephalopathy 149.55 22.82 75 8605 14820 32490026
Renal impairment 122.08 22.82 136 8544 91836 32413010
Fatigue 93.62 22.82 253 8427 350448 32154398
Yellow skin 65.91 22.82 24 8656 2153 32502693
Anaemia 61.04 22.82 163 8517 223461 32281385
Ocular icterus 60.82 22.82 25 8655 3107 32501739
Hepatitis C 57.51 22.82 39 8641 13479 32491367
Encephalopathy 54.75 22.82 56 8624 34201 32470645
Oesophageal varices haemorrhage 53.77 22.82 23 8657 3156 32501690
Asthenia 52.69 22.82 160 8520 235784 32269062
Haemoglobin decreased 52.19 22.82 105 8575 119566 32385280
Blood bilirubin unconjugated increased 50.69 22.82 15 8665 699 32504147
Portal hypertension 48.35 22.82 23 8657 4041 32500805
Drug interaction 45.93 22.82 145 8535 218040 32286806
Insomnia 44.87 22.82 89 8591 100259 32404587
Hepatitis C RNA increased 39.99 22.82 11 8669 393 32504453
Distributive shock 38.92 22.82 13 8667 902 32503944
Gastric varices haemorrhage 38.76 22.82 10 8670 278 32504568
Alanine aminotransferase increased 36.75 22.82 71 8609 78408 32426438
Child-Pugh-Turcotte score increased 33.66 22.82 7 8673 72 32504774
Bilirubin conjugated increased 33.46 22.82 17 8663 3441 32501405
Vomiting 29.79 22.82 133 8547 235424 32269422
Nausea 28.54 22.82 164 8516 320685 32184161
Chromaturia 27.45 22.82 26 8654 14452 32490394
Varices oesophageal 26.95 22.82 15 8665 3646 32501200
Drug ineffective 25.97 22.82 39 8641 383438 32121408
Alpha 1 foetoprotein increased 25.64 22.82 9 8671 725 32504121
Hepatic lesion 25.43 22.82 14 8666 3333 32501513
Immunosuppressant drug level increased 24.67 22.82 16 8664 5129 32499717
Acute on chronic liver failure 24.26 22.82 6 8674 140 32504706
Irritability 23.66 22.82 31 8649 24623 32480223
Death 23.01 22.82 42 8638 382475 32122371

Pharmacologic Action:

SourceCodeDescription
ATC J05AP09 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HCV infections
ATC J05AP52 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Antivirals for treatment of HCV infections
FDA MoA N0000190113 Breast Cancer Resistance Protein Inhibitors
FDA EPC N0000191257 Hepatitis C Virus Non-Nucleoside NS5B Palm Polymerase Inhibitor
FDA MoA N0000191258 RNA Replicase Inhibitors
FDA MoA N0000191272 UGT1A1 Inhibitors
CHEBI has role CHEBI:36044 anti-virus drug
CHEBI has role CHEBI:85180 nonstructural protein 5B inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Chronic hepatitis C indication 128302006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.38 acidic
pKa2 9.01 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 8501238 Sept. 17, 2028 USE OF DASABUVIR TO INHIBIT VIRAL REPLICATION FOR THE TREATMENT OF HCV INFECTION.
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 8501238 Sept. 17, 2028 USE OF DASABUVIR TO INHIBIT VIRAL REPLICATION FOR THE TREATMENT OF HCV INFECTION.
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 9139536 Nov. 9, 2028 TREATMENT OF HCV INFECTION USING DASABUVIR
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 9139536 Nov. 9, 2028 TREATMENT OF HCV INFECTION USING DASABUVIR
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 8188104 May 17, 2029 USE OF DASABUVIR TO INHIBIT VIRAL REPLICATION FOR THE TREATMENT OF HCV INFECTION.
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 8188104 May 17, 2029 USE OF DASABUVIR TO INHIBIT VIRAL REPLICATION FOR THE TREATMENT OF HCV INFECTION.
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 8642538 Sept. 10, 2029 TREATMENT OF HCV INFECTION USING PARITAPREVIR
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 8642538 Sept. 10, 2029 TREATMENT OF HCV INFECTION USING PARITAPREVIR
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 9006387 June 10, 2030 TREATMENT OF HCV INFECTION USING OMBITASVIR
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 9006387 June 10, 2030 TREATMENT OF HCV INFECTION USING OMBITASVIR
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 9044480 April 10, 2031 TREATMENT OF HCV INFECTION USING PARITAPREVIR
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 9044480 April 10, 2031 TREATMENT OF HCV INFECTION USING PARITAPREVIR
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 10201584 May 17, 2032 TREATMENT OF HCV INFECTION USING DASABUVIR/OMBITASVIR/PARITAPREVIR/RITONAVIR FIXED DOSE COMBINATION
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 8466159 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR WITH RIBAVIRIN.
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 8492386 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR, WITHOUT RIBAVIRIN
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 8680106 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR WITH RIBAVIRIN.
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 8685984 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR, WITHOUT RIBAVIRIN
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 8466159 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR WITH RIBAVIRIN.
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 8492386 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR, WITHOUT RIBAVIRIN
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 8680106 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR WITH RIBAVIRIN.
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 8685984 Sept. 4, 2032 TREATMENT OF HCV INFECTION USING PARITAPREVIR, OMBITASVIR, RITONAVIR, AND DASABUVIR, WITHOUT RIBAVIRIN
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 10201542 Oct. 18, 2033 TREATMENT OF HCV INFECTION USING DASABUVIR
EQ 250MG BASE;12.5MG, 75MG, 50MG VIEKIRA PAK (COPACKAGED) ABBVIE INC N206619 Dec. 19, 2014 DISCN TABLET ORAL 9629841 Oct. 18, 2033 TREATMENT OF HCV INFECTION USING DASABUVIR
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 10105365 Jan. 2, 2035 TREATMENT OF HCV INFECTION USING DASABUVIR/OMBITASVIR/PARITAPREVIR/RITONAVIR FIXED DOSE COMBINATION
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 9333204 Jan. 2, 2035 TREATMENT OF HCV INFECTION USING DASABUVIR/OMBITASVIR/PARITAPREVIR/RITONAVIR FIXED DOSE COMBINATION
EQ 200MG BASE;8.33MG;50MG;33.33MG VIEKIRA XR ABBVIE INC N208624 July 22, 2016 DISCN TABLET, EXTENDED RELEASE ORAL 9744170 Jan. 2, 2035 TREATMENT OF HCV INFECTION USING DASABUVIR/OMBITASVIR/PARITAPREVIR/RITONAVIR FIXED DOSE COMBINATION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
NS5B protein Enzyme EC50 8.74 CHEMBL

External reference:

IDSource
D10553 KEGG_DRUG
1456607-55-8 SECONDARY_CAS_RN
4034028 VANDF
CHEBI:85182 CHEBI
CHEMBL3137312 ChEMBL_ID
C588260 MESH_SUPPLEMENTAL_RECORD_UI
11270 IUPHAR_LIGAND_ID
9741 INN_ID
DB09183 DRUGBANK_ID
DE54EQW8T1 UNII
56640146 PUBCHEM_CID
1597381 RXNORM
30778 MMSL
31899 MMSL
d08322 MMSL
015829 NDDF
015830 NDDF
714104000 SNOMEDCT_US
714105004 SNOMEDCT_US
716018007 SNOMEDCT_US
725851005 SNOMEDCT_US
C3852512 UMLSCUI
CHEMBL3544985 ChEMBL_ID

Pharmaceutical products:

None