Cobicistat
Grundinformationen
- CAS
1004316-88-4- Standard-SMILES
CC(C)c1nc(CN(C)C(=O)N[C@@H](CCN2CCOCC2)C(=O)N[C@H](CC[C@H](Cc2ccccc2)NC(=O)OCc2cncs2)Cc2ccccc2)cs1- InChIKey
ZCIGNRJZKPOIKD-CQXVEOKZSA-N- Summenformel
- C40H53N7O5S2
- Durchschnittliche Molmasse
- 776 g/mol
- Monoisotopische Masse
- 775,35496016
Überblick
Cobicistat is a monocarboxylic acid amide obtained by formal condensation of the carboxy group of (2S)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-4-(morpholin-4-yl)butanoic acid with the amino group of 1,3-thiazol-5-ylmethyl [(2R,5R)-5-amino-1,6-diphenylhexan-2-yl]carbamate. Acts as a pharmacoenhancer in treatment of HIV-1 by inhibiting P450 enzymes that metabolise other medications.. It has a role as a P450 inhibitor. It is a carbamate ester, a monocarboxylic acid amide, a member of 1,3-thiazoles, a member of morpholines and a member of ureas.
Namen und Bezeichner
- Bevorzugter Name
- Cobicistat
- IUPAC
- 1,3-thiazol-5-ylmethyl N-[(2R,5R)-5-[[(2S)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamate
- Englischer Name
- Cobicistat
- Summenformel
- C40H53N7O5S2
- Molmasse
- 776.02
Namen und Synonyme
Cobicistat1004316-88-4GS-9350TybostGS 9350cobicistatum2,7,10,12-Tetraazatridecanoic acid, 12-methyl-13-[2-(1-methylethyl)-4-thiazolyl]-9-[2-(4-morpholinyl)ethyl]-8,11-dioxo-3,6-bis(phenylmethyl)-, 5-thiazolylmethyl ester, (3R,6R,9S)-LW2E03M5PG1,3-thiazol-5-ylmethyl N-[(2R,5R)-5-[[(2S)-2-[[methyl-[(2-propan-2-yl-1,3-thiazol-4-yl)methyl]carbamoyl]amino]-4-morpholin-4-ylbutanoyl]amino]-1,6-diphenylhexan-2-yl]carbamateCOBICISTAT, (R,R,S)-CHEBI:72291GENVOYA COMPONENT COBICISTAT
Weitere Namen anzeigen
Cobicistat (GS-9350)GS9350CS-753Genvoya.CobiclstatCobicistat D8
DTXSID00143269EVOTAZ COMPONENT COBICISTATSYMTUZA COMPONENT COBICISTATREZOLSTA COMPONENT COBICISTATSTRIBILD COMPONENT COBICISTATPREZCOBIX COMPONENT COBICISTAT1,3-thiazol-5-ylmethyl [(2R,5R)-5-{[(2S)-2-({[(2-isopropyl-1,3-thiazol-4-yl)methyl](methyl)carbamoyl}amino)-4-(morpholin-4-yl)butanoyl]amino}-1,6-diphenylhexan-2-yl]carbamate2,7,10,12-Tetraazatridecanoic acid, 12-methyl-13-(2-(1-methylethyl)-4-thiazolyl)-9-(2-(4-morpholinyl)ethyl)-8,11-dioxo-3,6-bis(phenylmethyl)-, 5-thiazolylmethyl ester, (3R,6R,9S)-
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 5,7
- Polarare Oberfläche (TPSA)
- 195 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 20
- Schwere Atome
- 54
- Formalladung
- 0
- Komplexität
- 1.120
Experimentelle und physikochemische Eigenschaften
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Used in Switzerland
Human Drugs
FDA approved drugs -> Active ingredient
EMA approved medicines: Human medicine
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Schmelzpunkt
- 50 · 50-54°C
- Siedepunkt
- 974.5 · 974.5±65.0 °C(Predicted)
- Dichte
- 1.228 · 1.228±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- Hygroscopic, Refrigerator, under inert atmosphere
- Löslichkeit
- Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- Aggregatzustand
- Solid
- pka
- 11.86 · 11.86±0.46(Predicted)
- Farbe
- White to Off-White
- Stabilität
- Hygroscopic
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Cobicistat
Ambiguous-DILI-concern
5
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Sicherheitsdaten
- Gefahrenhinweise
- Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315
Chemie und Industrie
Pharmakologische Informationen
ATC Code
J05AR14
V - Various
QV - Various
Protein Binding97-98% bound to human plasma proteins.
Mechanism of Action
Cobicistat is a mechanism-based inhibitor of cytochrome P450 3A (CYP3A) isoforms. Inhibition of CYP3A-mediated metabolism by cobicistat increases the systemic exposure of CYP3A substrates atazanavir and darunavir and therefore enables increased anti-viral activity at a lower dosage. Cobicistat does not have any anti-HIV activity on its own.
Biological Half-LifeThe terminal plasma half-life of cobicistat is approximately 3 to 4 hours.
Metabolism/MetabolitesCobicistat is metabolized by CYP3A and to a minor extent by CYP2D6 enzymes and does not undergo glucuronidation.
FDA Pharmacological Classification
LW2E03M5PG
COBICISTAT
Mechanisms of Action [MoA] - Cytochrome P450 3A Inhibitors
Established Pharmacologic Class [EPC] - Cytochrome P450 3A Inhibitor
Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors
Mechanisms of Action [MoA] - Cytochrome P450 2D6 Inhibitors
MeSH Pharmacological Classification
Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS.
Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP3A.
Absorption, Distribution and Excretion
Median peak plasma concentrations were observed at 3.5 hours post-dose.
With single dose administration of [14C] cobicistat after multiple dosing of cobicistat for six days, the mean percent of the administered dose excreted in feces and urine was 86.2% and 8.2%, respectively.
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