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
Weitere Namen anzeigen
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
- Formalladung
- 0
- Komplexität
- 938
Experimentelle und physikochemische Eigenschaften
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)
- Farbe
- Pale Brown to Light Brown
- 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)
- InChIKey
- NBRBXGKOEOGLOI-UHFFFAOYSA-N
- SMILES
- CS(NC1=CC=C2C(=C1)C=CC(C1=CC(N3C(=O)NC(=O)C=C3)=CC(C(C)(C)C)=C1OC)=C2)(=O)=O
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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
Toxikologische Informationen
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Aquatic Chronic 4
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
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. 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.
FDA Pharmacological Classification
DE54EQW8T1
DASABUVIR
Established Pharmacologic Class [EPC] - Hepatitis C Virus Non-Nucleoside NS5B Palm Polymerase Inhibitor
Mechanisms of Action [MoA] - RNA Replicase Inhibitors
Mechanisms of Action [MoA] - UGT1A1 Inhibitors
Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors
Absorption, Distribution and Excretion
Dasabuvir reaches peak plasma concentration 4 hours after administration. The absolute bioavailability of Dasabuvir is 70%.
Dasabuvir is mainly excreted in the feces (94.4%) with very little excreted in the urine (2%). 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.
Dasabuvir has a volume of distribution at steady state of 149 liters.
Clearance of Dasabuvir has not been determined.
Anwendungen
VerwendenDasabuvir is an antiviral drug used in the treatment of chronic hepatitis C virus (HCV) infection.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
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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