Elbasvir
Grundinformationen
- CAS
1370468-36-2- Standard-SMILES
COC(=O)N[C@H](C(=O)N1CCC[C@H]1c1ncc(-c2ccc3c(c2)O[C@@H](c2ccccc2)n2c-3cc3cc(-c4cnc([C@@H]5CCCN5C(=O)[C@@H](NC(=O)OC)C(C)C)[nH]4)ccc32)[nH]1)C(C)C- InChIKey
BVAZQCUMNICBAQ-PZHYSIFUSA-N- Summenformel
- C49H55N9O7
- Durchschnittliche Molmasse
- 882 g/mol
- Monoisotopische Masse
- 881,42244513
Überblick
Elbasvir is a complex organic heterotetracyclic compound that is a hepatitis C virus nonstructural protein 5A inhibitor used in combination with grazoprevir (under the brand name Zepatier) for treatment of chronic HCV genotypes 1 or 4 infection in adults. It has a role as an antiviral drug, a hepatoprotective agent and a hepatitis C virus nonstructural protein 5A inhibitor. It is a carbamate ester, a member of imidazoles, a ring assembly, an organic heterotetracyclic compound, a N-acylpyrrolidine and a L-valine derivative.
Namen und Bezeichner
- Bevorzugter Name
- Elbasvir
- IUPAC
- methyl N-[(2S)-1-[(2S)-2-[5-[(6S)-3-[2-[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]-6-phenyl-6H-indolo[1,2-c][1,3]benzoxazin-10-yl]-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate
- Englischer Name
- Elbasvir
- Summenformel
- C49H55N9O7
- Molmasse
- 882.02
Namen und Synonyme
Elbasvir1370468-36-2MK-8742MK 8742632L571YDKMK8742CHEBI:132967methyl N-[(2S)-1-[(2S)-2-[5-[(6S)-3-[2-[(2S)-1-[(2S)-2-(methoxycarbonylamino)-3-methylbutanoyl]pyrrolidin-2-yl]-1H-imidazol-5-yl]-6-phenyl-6H-indolo[1,2-c][1,3]benzoxazin-10-yl]-1H-imidazol-2-yl]pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamateelbasvirummethyl N-((2S)-1-((2S)-2-(5-((6S)-3-(2-((2S)-1-((2S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-6-phenyl-6H-indolo(1,2-c)(1,3)benzoxazin-10-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-yl)carbamateRefChem:136463DTXCID9082534
Weitere Namen anzeigen
AlbasvirD6-ElbasvirMK-8742 ElbasvirElbasvir/MK-8742Elbasvir, 10 mM in DMSOdimethyl ((2s,2's)-((2s,2's)-(((s)-6-phenyl-6h-benzo[5,6][1,3]oxazino[3,4-a]indole-3,10-diyl)bis(1h-imidazole-2,5-diyl))bis(pyrrolidine-2,1-diyl))bis(3-methyl-1-oxobutane-1,2-diyl))dicarbamate
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 6,7
- Polarare Oberfläche (TPSA)
- 189 Ų
- H-Brücken-Donoren
- 4
- H-Brücken-Akzeptoren
- 9
- Frei drehbare Bindungen
- 13
- Schwere Atome
- 65
- Formalladung
- 0
- Komplexität
- 1.680
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antiviral Agents; NS5A Inhibitors
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Dichte
- 1.4 · 1.40±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 33 mg/ml; · DMF: 33 mg/ml; DMSO: 20 mgm/l; Ethanol: 33 mg/ml; Ethanol:PBS (pH 7.2)(1:2): 0.33 mg/ml
- Aggregatzustand
- A crystalline solid
- pka
- 11.22 · 11.22±0.46(Predicted)
- Farbe
- White to yellow
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Warning
H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 35 reports by companies from 1 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Hazard Classes and CategoriesAquatic Chronic 1 (100%)
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Sicherheitsdaten
- Alarmwort
- Warnung
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H226
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingElbasvir is more than 99.9% bound to plasma proteins. It binds both human serum albumin and α1-acid glycoprotein.
PharmacodynamicsElbasvir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotypes 1a, 1b, and 4.
Mechanism of Action
Elbasvir is an inhibitor of the HCV non-structural protein 5A. While the precise role of this protein is unknown, it is essential to viral replication and virion assembly.[synthesis] Potential modes of action of NS5A inhibitors like elbasvir include blocking signaling interactions, redistribution of NS5A from the endoplasmic reticulum to the surface of lipid droplets, and modification of the HCV replication complex. Computational target-based _in silico_ research suggests that elbasvir may carry activity at several proteins required for replication of SARS-CoV-2 - namely RNA-dependent RNA polymerase, helicase, and papain-like proteinase - although specific activity has yet to be affirmed by follow-up clinical studies.
Biological Half-LifeThe geometric mean apparent terminal half-life for elbasvir is 24 hours in HCV-infected subjects.
Metabolism/MetabolitesElbasvir is partially eliminated by oxidative metabolism meditated by CYP3A. No circulating metabolites of elbasvir have been detected in human plasma.
FDA Pharmacological Classification
632L571YDK
ELBASVIR
Established Pharmacologic Class [EPC] - Hepatitis C Virus NS5A Inhibitor
Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors
Elbasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of elbasvir is as a Breast Cancer Resistance Protein Inhibitor.
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