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Details

Stereochemistry ACHIRAL
Molecular Formula C26H27N3O5S
Molecular Weight 493.575
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DASABUVIR

SMILES

COC1=C(C=C(C=C1C2=CC3=CC=C(NS(C)(=O)=O)C=C3C=C2)N4C=CC(=O)NC4=O)C(C)(C)C

InChI

InChIKey=NBRBXGKOEOGLOI-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C26H27N3O5S
Molecular Weight 493.575
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/26567871

Dasabuvir is a non-nucleoside inhibitor of the hepatitis C virus (HCV) NS5B palm polymerase inhibitor. It is used in the treatment of adult patients with chronic hepatitis C virus infection in combination with ombitasvir, paritaprevir, and ritonavir as the combination product Viekira Pak. Viekira PAK combines three direct-acting antiviral agents with distinct mechanisms of action and non-overlapping resistance profiles to target HCV at multiple steps in the viral lifecycle. Dasabuvir is extensively evaluated in large clinical trials and shown excellent sustained virological response among hepatitis C virus genotype1 patient population in combination with other oral direct acting antivirals, with good safety profile and tolerance.

Originator

Approval Year

2014
447
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8146
 2.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8307
VIEKIRA PAK (COPACKAGED)

Approved Use

Treatment of adult patients with chronic hepatitis C virus (HCV): genotype 1b without cirrhosis or with compensated cirrhosis, genotype 1a without cirrhosis or with compensated cirrhosis for use in combination with ribavirin.

Launch Date

1.4189472E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2110 ng/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
320 ng/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
200 mg 2 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
912 ng/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
400 mg 2 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1130 ng/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
600 mg 2 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
15800 ng × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
2620 ng × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
200 mg 2 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7050 ng × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
400 mg 2 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
8800 ng × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
600 mg 2 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.52 h
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
6.87 h
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
400 mg 2 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
6.87 h
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
600 mg 2 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.1%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
1000 mg 2 times / day multiple, oral
dose: 1000 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.1%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
200 mg 2 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.1%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
400 mg 2 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.1%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/28258380/
600 mg 2 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
DASABUVIR plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1600 mg 2 times / day multiple, oral
Highest studied dose
Dose: 1600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
healthy, adult
Health Status: healthy
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
2000 mg single, oral
Highest studied dose
Dose: 2000 mg
Route: oral
Route: single
Dose: 2000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
healthy, adult
Health Status: healthy
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
600 mg 2 times / day multiple, oral
Dose: 600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 600 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
unhealthy, adult
Health Status: unhealthy
Condition: hepatitis C virus
Age Group: adult
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
Sources:
https://pubmed.ncbi.nlm.nih.gov/28258380
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:85182
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85182
ChemicalBook
CB62681991
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB62681991
MolPort
MolPort-035-679-559
https://www.molport.com/shop/molecule-link/MolPort-035-679-559
ZINC
ZINC000095616937
http://zinc15.docking.org/substances/ZINC000095616937
PubMed

PubMed

TitleDatePubMed
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.
2015 Sep
New direct-acting antivirals in hepatitis C therapy: a review of sofosbuvir, ledipasvir, daclatasvir, simeprevir, paritaprevir, ombitasvir and dasabuvir.
2016
Dasabuvir (ABT333) for the treatment of chronic HCV genotype I: a new face of cure, an expert review.
2016
Patents

Patents

20090186912
3
20110070193
6
2012014913
3
2013217876
3
20525198
3
8188104
3

Sample Use Guides

In Vivo Use Guide
250 mg tablet twice daily (morning and evening) with a meal without regard to fat or calorie content.
Route of Administration: Oral
In Vitro Use Guide
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. The median EC50 values of dasabuvir against HCV replicons containing NS5B genes from a panel of genotype 1a and 1b isolates from treatment-naïve subjects were 0.6 nM (range 0.4 nM to 2.1 nM; n = 11) and 0.3 nM (range 0.2 nM to 2 nM; n = 10), respectively.
Substance Class Chemical
Created
by admin
on Fri Dec 16 21:28:58 UTC 2022
Edited
by admin
on Fri Dec 16 21:28:58 UTC 2022
Record UNII
DE54EQW8T1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DASABUVIR
DASH   INN   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
dasabuvir [INN]
Common Name English
N-(6-(3-TERT-BUTYL-5-(2,4-DIOXO-3,4-DIHYDROPYRIMIDIN-1(2H)-YL)-2-METHOXYPHENYL)NAPHTHALEN-2-YL)METHANESULFONAMIDE
Systematic Name English
DASABUVIR [MI]
Common Name English
METHANESULFONAMIDE, N-(6-(5-(3,4-DIHYDRO-2,4-DIOXO-1(2H)-PYRIMIDINYL)-3-(1,1-DIMETHYLETHYL)-2-METHOXYPHENYL)-2-NAPHTHALENYL)-
Systematic Name English
DASABUVIR [USAN]
Common Name English
ABT-333
Code English
Dasabuvir [WHO-DD]
Common Name English
DASABUVIR [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC J05AX66
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
WHO-ATC J05AP09
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
WHO-ATC J05AP52
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
FDA ORPHAN DRUG 484715
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
NCI_THESAURUS C281
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
NDF-RT N0000191257
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
WHO-ATC J05AX16
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
Code System Code Type Description
LACTMED
Dasabuvir
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
CAS
1132935-63-7
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
EVMPD
SUB131059
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
USAN
BC-08
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
FDA UNII
DE54EQW8T1
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
PUBCHEM
56640146
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
RXCUI
1597381
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY RxNorm
DRUG BANK
DB09183
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
WIKIPEDIA
Dasabuvir
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
MERCK INDEX
M11828
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
ChEMBL
CHEMBL3137312
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
CAS
1221573-79-0
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
NO STRUCTURE GIVEN
DAILYMED
DE54EQW8T1
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
CHEBI
85182
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
EPA CompTox
DTXSID301025953
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
NDF-RT
N0000191272
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY UGT1A1 Inhibitors [MoA]
INN
9741
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
NDF-RT
N0000190113
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY Breast Cancer Resistance Protein Inhibitors [MoA]
DRUG CENTRAL
4914
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
NDF-RT
N0000191258
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY RNA Replicase Inhibitors [MoA]
NCI_THESAURUS
C123880
Created by admin on Fri Dec 16 21:28:58 UTC 2022 , Edited by admin on Fri Dec 16 21:28:58 UTC 2022
PRIMARY
Related Record Type Details
Structure of DASABUVIR
EXCRETED UNCHANGED
URINE
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of DASABUVIR
EXCRETED UNCHANGED
FECAL
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
Structure of 2-(5-(2,4-DIOXOHEXAHYDROPYRIMIDIN-1-YL)-3-(6-(METHANESULFONAMIDO)-2-NAPHTHYL)-2-METHOXY-PHENYL)-2-METHYL-PROPANOIC ACID
METABOLITE -> PARENT
FECAL
Structure of A-1039710 GLUCURONIDE
METABOLITE -> PARENT
PLASMA; URINE
Structure of (2-(5-(2,4-DIOXOPYRIMIDIN-1-YL)-3-(6-(METHANESULFONAMIDO)-2-NAPHTHYL)-2-METHOXY-PHENYL)-2-METHYL-PROPYL) HYDROGEN SULFATE
METABOLITE -> PARENT
PLASMA; URINE
Structure of N-(6-(5-(2,4-DIOXOPYRIMIDIN-1-YL)-2-HYDROXY-3-(2-HYDROXY-1,1-DIMETHYL-ETHYL)PHENYL)-2-NAPHTHYL)METHANESULFONAMIDE
METABOLITE -> PARENT
PLASMA; URINE
Structure of (2S,3S,4S,5R,6R)-6-(2-(5-(2,4-DIOXOPYRIMIDIN-1-YL)-3-(6-(METHANESULFONAMIDO)-2-NAPHTHYL)-2-METHOXY-PHENYL)-2-METHYL-PROPOXY)-3,4,5-TRIHYDROXY-TETRAHYDROPYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
FECAL; PLASMA; URINE
Structure of A-1041392
METABOLITE -> PARENT
PLASMA
Structure of A-1039710
METABOLITE -> PARENT
FECAL
Related Record Type Details
Structure of DASABUVIR
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC
blood-to-plasma ratio PHARMACOKINETIC
NIH
NCATS
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