Dasabuvir

HCID 56640146CAS 1132935-63-7

Grundinformationen

Standard-SMILES
COc1c(-c2ccc3cc(NS(C)(=O)=O)ccc3c2)cc(-n2ccc(=O)[nH]c2=O)cc1C(C)(C)C
InChIKey
NBRBXGKOEOGLOI-UHFFFAOYSA-N
Summenformel
C26H27N3O5S
Durchschnittliche Molmasse
493,6 g/mol
Monoisotopische Masse
493,16714196

Überblick

Dasabuvir is a member of the class of pyrimidone, which is (as the monohydrate of its sodium salt) in combination with ombitasvir, paritaprevir and ritonavir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as cirrhosis of the liver. It has a role as an antiviral drug and a nonnucleoside hepatitis C virus polymerase inhibitor. It is a member of naphthalenes, a sulfonamide, an aromatic ether and a pyrimidone. It is functionally related to a uracil.

Namen und Bezeichner

Bevorzugter Name
Dasabuvir
IUPAC
N-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide
Englischer Name
ABT-333
Summenformel
C26H27N3O5S
Molmasse
493.57

Namen und Synonyme

Dasabuvir1132935-63-7ABT-333ABT333exvieraDE54EQW8T1N-(6-(3-tert-Butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamideABT 333CHEBI:85182DTXSID301025953Methanesulfonamide, N-(6-(5-(3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl)-3-(1,1-dimethylethyl)-2-methoxyphenyl)-2-naphthalenyl)-N-[6-[3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl]naphthalen-2-yl]methanesulfonamide
Weitere Namen anzeigen
CS-2000ABT-333/DasabuvirDasabuvir (ABT-333)Dasabuvir-13C 15N2 D3Dasabuvir, 10 mM in DMSON-{6-[3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl]-2-naphthyl}methanesulfonamideN-{6-[5-(2,4-Dioxo-3,4-dihydro-1(2H)-pyrimidinyl)-2-methoxy-3-(2-methyl-2-propanyl)phenyl]-2-naphthyl}methanesulfonamide
N-{6-[3-tert-butyl-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl]naphthalen-2-yl}methanesulfonamidedasabuvirumN-(6-(3-tert-butyl-5-(2,4-dioxopyrimidin-1-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamideRefChem:585200J05AP09DTXCID901510205805-439-9N-(6-(3-(tert-butyl)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2-methoxyphenyl)naphthalen-2-yl)methanesulfonamide

Datenbank-Bezeichner

CAS
1132935-63-7
PubChem CID
56640146
DTXSID
DTXSID301025953
ChEMBL
CHEMBL3137312
ChEBI
CHEBI:85182
UNII
DE54EQW8T1
EC Number
805-439-9
Nikkaji
J3.299.348F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,3
Polarare Oberfläche (TPSA)
113 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
6
Schwere Atome
35

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsBreast Feeding; Lactation; Milk, Human; Antiviral Agents

Physikochemische Eigenschaften

Schmelzpunkt
192 oC · >192oC (dec.)
Dichte
1.317 · 1.317±0.06 g/cm3(Predicted)
storage temp.
-20 °C · Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit
Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated)
Aggregatzustand
Solid
pka
8.52 · 8.52±0.30(Predicted)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory InformationStatus: Active Update: 08-05-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/5761
Hazard Classes and CategoriesAquatic Chronic 4 (100%)

Toxikologische Informationen

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

wgk
WGK 3
Speicherklasse
11 - Combustible Solids
Hazard Classifications
Aquatic Chronic 4

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

Protein BindingDasabuvir is greater than 99.5% bound to human plasma proteins.
PharmacodynamicsDasabuvir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotype 1.
Mechanism of Action · 1 Eintrag

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. 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. 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.

Biological Half-LifeThe half-life of elimination of dasabuvir is 5.5 to 6 hours.
Metabolism/MetabolitesDasabuvir is predominantly metabolized by CYP2C8, and to a lesser extent by CYP3A.

Anwendungen

VerwendenDasabuvir is an antiviral drug used in the treatment of chronic hepatitis C virus (HCV) infection.

Anbieter50 Anbieter

BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.+86-18600796368 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
湖北科乐精细化工有限公司027-59101668 19945030958 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A member of the class of pyrimidone, which is (as the monohydrate of its sodium salt) in combination with ombitasvir, paritaprevir and ritonavir (under the trade name Viekira Pak) for treatment of chronic hepatitis C virus genotype 1 infection as well as c rrhosis of the liver.

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