Abiraterone Acetate
ZYTIGA · (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-yl acetate · 17-(3-pyridyl)-5,16-androstadien-3beta-acetate · ABITATERONE ACETATE · Abiraterone Acotate · (3β)-17-(3-pyridinyl) androsta-5,16-dien-3-yl acetate · (3)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol Acetate (Ester) · (3beta)-17-(3-pyridinyl)-Androsta-5,16-dien-3-ol acetate (ester)
Identifikatoren & physikalische Daten
| CAS No. | 154229-18-2 |
|---|---|
| Summenformel | C26H33NO2 |
| Durchschnittliche Molmasse | 391,5 g/mol |
| Monoisotopische Masse | 391,2511293 g/mol |
| SMILES | CC(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@]2(C)C(c4cccnc4)=CC[C@@H]32)C1 |
| InChIKey | UVIQSJCZCSLXRZ-UBUQANBQSA-N |
| PubChem CID | 9821849 |
| ChEMBL | CHEMBL271227 |
| ChEBI | CHEBI:68639 |
| EC No. | 620-314-7 |
| DTXSID | DTXSID3049043 |
Chemische & physikalische Eigenschaften
| XLogP | 5,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 39,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 29 |
| Formalladung | 0 |
| Komplexität | 739 |
| Arzneimittel | Pharmaceuticals -> Used in Switzerland |
| Human Drugs | FDA approved drugs -> Active ingredientEMA approved medicines: Human medicine |
| Schmelzpunkt | 127-130°C |
| Siedepunkt | 506.7±50.0 °C(Predicted) |
| Dichte | 1.14±0.1 g/cm3(Predicted) |
| Lagerbedingungen | -20°C |
| Löslichkeit | Chloroform (Slightly), DMSO (Sparingly), Methanol (Sparingly) |
| pKa (Säurekonstante) | 5.31±0.12(Predicted) |
| Aggregatzustand | powder |
| Farbe | white to beige |
| InChIKey | UVIQSJCZCSLXRZ-UBUQANBQSA-N |
| SMILES | C1[C@@]2(C)C(=CC[C@]3([H])[C@]2([H])CC[C@]2(C)C(C4=CC=CN=C4)=CC[C@@]32[H])C[C@@H](OC(=O)C)C1 |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 5.1% (2 of 39) of reports.DangerH302 (74.4%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P264, P270, P273, P280, P301+P317, P318, P319, P330, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Hazard Traits - Developmental ToxicityReproductive Toxicity |
| Hazard Classes and Categories | Acute Tox. 4 (74.4%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Abiraterone acetatevMost-DILI-concern8Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 2937290000 |
| RTECS-Nr. | BV7992100 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrenklasse | Aquatic Chronic 1Repr. 1BSTOT RE 2 |
Anwendungen & Verwendung
Beschreibung
In April 2011, the United States FDA approved abiraterone acetate (CB7630) in combination with the steroid prednisone for the treatment of metastatic castration-resistant prostate cancer (mCRPC) for patients who were previously treated with a docetaxel containing regimen for late-stage disease. Abiraterone acetate affects prostate, testicular, and adrenal androgens by irreversibly inhibiting both the lyase and hydroxylase activity of cytochrome P450 17A (CYP17) signaling pathways (IC50's of 2.9 and 4 nM, respectively) thereby decreasing testosterone levels.Most common serious adverse events for abiraterone acetate versus placebo included fluid retention (30.5% vs. 22.3%), hypokalemia (17.1% vs. 8.4%), hypertension (9.7% vs. 7.9%), hepatic transaminase abnormalities (10.4% vs. 8.1%), and cardiac abnormalities (13.3% vs. 10.4%).
Verwenden
Abiraterone acetate is a novel steroidal inhibitor of human Cytochrome P450 (17α-Hydroxylase-C17,20-lyase): potential agent for the treatment of prostatic cancer.