DASABUVIR

First approved in 2014

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206619Orig1s011lbl.pdf
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

Targets

Primary Target	Pharmacology	Condition	Potency
polyprotein 3 Target ID: 951475.0 Gene Symbol: HCVgp1 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206619Orig1s011lbl.pdf	Inhibitor 8297		2.8 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis C 42 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/206619Orig1s011lbl.pdf	Primary		Approved 8429	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 2014

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

F_unbound

Value	Dose	Analyte	Population
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

Dose	Population	Adverse 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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Dasabuvir: A Non-Nucleoside Inhibitor of NS5B for the Treatment of Hepatitis C Virus Infection.	2014	24882169
Interferon-free therapy for hepatitis C: The hurdles amid a golden era.	2015 Sep	25937625
New direct-acting antivirals in hepatitis C therapy: a review of sofosbuvir, ledipasvir, daclatasvir, simeprevir, paritaprevir, ombitasvir and dasabuvir.	2016	26651915
Dasabuvir (ABT333) for the treatment of chronic HCV genotype I: a new face of cure, an expert review.	2016	26567871

Patents

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 15 17:02:18 GMT 2023` Edited by `admin` on `Fri Dec 15 17:02:18 GMT 2023`
Record UNII	DE54EQW8T1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DASABUVIR

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