Grazoprevir
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Grundinformationen
- CAS
1350462-55-3- Standard-SMILES
C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H]2CN1C(=O)[C@H](C(C)(C)C)NC(=O)O[C@@H]1C[C@H]1CCCCCc1nc3ccc(OC)cc3nc1O2)C(=O)NS(=O)(=O)C1CC1- InChIKey
OBMNJSNZOWALQB-NCQNOWPTSA-N- Summenformel
- C38H50N6O9S
- Durchschnittliche Molmasse
- 766,9 g/mol
- Monoisotopische Masse
- 766,33599818
Überblick
Grazoprevir is an azamacrocyclic compound that is a hepatitis C protease inhibitor used in combination with elbasvir (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 protease inhibitor. It is a carbamate ester, a lactam, an aromatic ether, a quinoxaline derivative, a member of cyclopropanes, an azamacrocycle and a N-sulfonylcarboxamide.
Namen und Bezeichner
- Bevorzugter Name
- Grazoprevir
- IUPAC
- (1R,18R,20R,24S,27S)-24-tert-butyl-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamide
- Englischer Name
- MK 5172 hydrate
- Summenformel
- C38H50N6O9S.H2O
- Molmasse
- 784.91868
Namen und Synonyme
Grazoprevir1350514-68-9MK5172MK-5172 ANHYDROUS(1R,18R,20R,24S,27S)-24-tert-butyl-N-[(1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl]-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3,5(10),6,8,11-pentaene-27-carboxamideCHEBI:132975DTXSID50159234MK-5172 MONOHYDRATEDTXSID00159229grazoprevirum(1R,18R,20R,24S,27S)-24-tert-butyl-N-((1R,2S)-1-(cyclopropylsulfonylcarbamoyl)-2-ethenylcyclopropyl)-7-methoxy-22,25-dioxo-2,21-dioxa-4,11,23,26-tetrazapentacyclo(24.2.1.03,12.05,10.018,20)nonacosa-3,5(10),6,8,11-pentaene-27-carboxamideRefChem:782705
Weitere Namen anzeigen
AnapivirMK5172 hydrateMK 5172 hydrateMK-5172 (hydrate)Grazoprevir hydrate (MK-5172 hydrate)MK5172 HYDRATEMK 5172 HYDRATE(33R,35S,91R,92R,5S)-5-(tert-butyl)-N-((1R,2S)-1-((cyclopropylsulfonyl)carbamoyl)-2-vinylcyclopropyl)-17-methoxy-4,7-dioxo-2,8-dioxa-6-aza-1(2,3)-quinoxalina-3(3,1)-pyrrolidina-9(1,2)-cyclopropanacyclotetradecaphane-35-carboxamide Hydrate
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 4,7
- Polarare Oberfläche (TPSA)
- 204 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 11
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 54
- Formalladung
- 0
- Komplexität
- 1.580
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antiviral Agents; Protease Inhibitors
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- 50 mg/mL · DMSO : 50 mg/mL (63.70 mM; Need ultrasonic)H2O : < 0.1 mg/mL (insoluble)
- Aggregatzustand
- Powder
- Farbe
- White to off-white
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
H373 (100%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
P260, P319, 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 CategoriesSTOT RE 2 (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 H373
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein BindingGrazoprevir is more than 98.8% bound to plasma proteins. It binds both human serum albumin and α1-acid glycoprotein.
PharmacodynamicsGrazoprevir is classified as a direct-acting antiviral (DAA) and prevents viral replication in HCV genotypes 1a, 1b, and 4.
Mechanism of Action
Grazoprevir is a second generation NS3/4a protease inhibitor used to inhibit viral HCV replication. NS3/4a protease is an integral part of viral replication and mediates the cleavage the virally encoded polyprotein to mature proteins (NS3, NS4A, NS4B, NS5A and NS5B). Grazoprevir inhibits the NS3/4protease enzymes of HCV genotype 1a, 1B, and 4 with IC50 values of 7pM, 4pM, and 62pM, respectively.
Biological Half-LifeThe geometric mean apparent terminal half-life for Grazoprevir is 31 hours in HCV-infected subjects.
Metabolism/MetabolitesGrazoprevir is partially eliminated by oxidative metabolism meditated by CYP3A. No circulating metabolites of have been detected in human plasma.
FDA Pharmacological Classification
8YE81R1X1J
GRAZOPREVIR ANHYDROUS
Mechanisms of Action [MoA] - HCV NS3/4A Protease Inhibitors
Established Pharmacologic Class [EPC] - Hepatitis C Virus NS3/4A Protease Inhibitor
Mechanisms of Action [MoA] - Breast Cancer Resistance Protein Inhibitors
Mechanisms of Action [MoA] - Cytochrome P450 3A Inhibitors
MeSH Pharmacological Classification
Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
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