8-Hydroxyefavirenz
8-HydroxyEfavirenz · Rac 8-hydroxy efavirenz · 8-hydroxy Efavirenz (Standard) · 8-Hydroxyefavirenz/205754-33-2 · Efavirenz Impurity 11(8-Hydroxy Efavirenz) · (4S)-6-chloro-4-(2-cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one · 6-Chloro-4-(cyclopropyl-d4-ethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one · 2H-3,1-Benzoxazin-2-one,6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-8-hydroxy-4-(trifluoromethyl)-, (4S)-
Identifikatoren & physikalische Daten
| CAS No. | 205754-33-2 |
|---|---|
| Summenformel | C14H9ClF3NO3 |
| Durchschnittliche Molmasse | 331,67 g/mol |
| Monoisotopische Masse | 331,0223053 g/mol |
| SMILES | O=C1Nc2c(O)cc(Cl)cc2[C@@](C#CC2CC2)(C(F)(F)F)O1 |
| InChIKey | OOVOMPCQLMFEDT-ZDUSSCGKSA-N |
| PubChem CID | 487643 |
| ChEMBL | CHEMBL1309 |
| DTXSID | DTXSID50942769 |
Chemische & physikalische Eigenschaften
| XLogP | 3,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 58,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 551 |
| Arzneimittel | Pharmaceuticals -> Metabolite of Efavirenz |
| Schmelzpunkt | 144-154°C |
| Siedepunkt | 373.6±42.0 °C(Predicted) |
| Dichte | 1+-.0.1 g/cm3(Predicted) |
| Lagerbedingungen | Store at -20°C |
| Löslichkeit | Acetonitrile: solubleDMSO: solubleMethanol: soluble |
| Aggregatzustand | A solid |
| pKa (Säurekonstante) | 7.18±0.40(Predicted) |
| Farbe | White to off-white |
| InChI | InChI=1S/C14H9ClF3NO3/c15-8-5-9-11(10(20)6-8)19-12(21)22-13(9,14(16,17)18)4-3-7-1-2-7/h5-7,20H,1-2H2,(H,19,21)/t13-/m0/s1 |
| InChIKey | OOVOMPCQLMFEDT-ZDUSSCGKSA-N |
| SMILES | N1C2=C(O)C=C(Cl)C=C2[C@@](C#CC2CC2)(C(F)(F)F)OC1=O |
Anwendungen & Verwendung
Beschreibung
8-hydroxy Efavirenz is a major oxidative metabolite of the non-nucleoside reverse transcriptase inhibitor efavirenz . 8-hydroxy Efavirenz is formed when efavirenz is metabolized by the cytochrome P450 (CYP) isoform CYP2B6. It induces apoptosis in rat primary hippocampal neurons and loss of dendritic spines in rat primary hippocampal neuronal cultures when used at a concentration of 0.01 μM.
Verwenden
A labellebed metabolite of Efavirenz, a nonnucleoside HIV-1 reverse transcriptase inhibitor