Abiraterone
(3S,8R,9S,10R,13S,14S)-10,13-diMethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol · Cb-7598 · Aberration · 7-Keto Abiraterone Acetate · (3β)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol · Androsta-5,16-dien-3-ol, 17-(3-pyridinyl)-, (3beta)- · CS-211 · Abiron
Identifikatoren & physikalische Daten
| CAS No. | 154229-19-3 |
|---|---|
| Summenformel | C24H31NO |
| Durchschnittliche Molmasse | 349,5 g/mol |
| Monoisotopische Masse | 349,24056461 g/mol |
| SMILES | C[C@]12CC[C@H](O)CC1=CC[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12 |
| InChIKey | GZOSMCIZMLWJML-VJLLXTKPSA-N |
| PubChem CID | 132971 |
| ChEMBL | CHEMBL254328 |
| ChEBI | CHEBI:68642 |
| EC No. | 810-941-6 |
| DTXSID | DTXSID80879993 |
Chemische & physikalische Eigenschaften
| XLogP | 4,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 33,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 636 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Metabolite of Abiraterone acetate |
| Human Drugs | Hormones and antihormones |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 227-228 °C(Solv: toluene (108-88-3)) |
| Siedepunkt | 500.2±50.0 °C(Predicted) |
| Dichte | 1.14±0.1 g/cm3(Predicted) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform (Slightly), Methanol (Slightly) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 14.71±0.70(Predicted) |
| Farbe | White to Pale Yellow |
| InChIKey | GZOSMCIZMLWJML-DROLTIPTNA-N |
| SMILES | C[C@]12CC[C@]3([H])[C@]4(CC[C@H](O)CC4=CC[C@@]3([H])[C@]1([H])CC=C2C1=CN=CC=C1)C |&1:1,4,6,9,15,17,r| |
| CAS Datenbank | 154229-19-3 |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH360 (57.1%): May damage fertility or the unborn child [Danger Reproductive toxicity]P203, P260, P273, P280, P318, P319, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 7 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Status: Active Update: 01-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/31684 |
| Hazard Classes and Categories | Repr. 1B (57.1%) |
| Hepatotoxicity | Serum aminotransferase elevations occur in up to 13% of patients treated with abiraterone compared with 1% to 8% receiving placebo or a comparator drug, but the abnormalities are generally mild, transient and not associated with symptoms or jaundice. ALT elevations above 5 times the upper limit of normal (ULN) occur in 6% of abiraterone treated vs |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)AbirateroneDILI PositiveDOI:10.1016/j.drudis.2019.09.022 |
| Alarmwort | Warnung |
| Gefahrenhinweise | Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302 |
Anwendungen & Verwendung
History
Abiraterone (brand name: Zytiga) is an anti-cancer drug developed by Centocor Ortho Biotech Inc. It was first approved by the FDA on 28 April 2011 for the treatment of advanced prostate cancer. In December 2012, the FDA expanded Zytiga's approved use to include treatment of men with advanced (metastatic) castration-resistant prostate cancer prior to chemotherapy. By February 2018, the FDA further approved Zytiga (abiraterone acetate) in combination with prednisone for the treatment of early metastatic prostate cancer.
Verwenden
Abiraterone, a steroidal cytochrome P 450 17α-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent pr ostate cancer.