Dutasteride
Avodart · (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(2,5-Bis(trifluoroMethyl)phenyl)-4a,6a-diMethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxaMide · Avolve · Duagen · (5α,17β)- · GI 198745 · utasteride · DUTASTERIDE
Identifikatoren & physikalische Daten
| CAS No. | 164656-23-9 |
|---|---|
| Summenformel | C27H30F6N2O2 |
| Durchschnittliche Molmasse | 528,5 g/mol |
| Monoisotopische Masse | 528,22114718 g/mol |
| SMILES | C[C@]12C=CC(=O)N[C@@H]1CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](C(=O)Nc3cc(C(F)(F)F)ccc3C(F)(F)F)CC[C@@H]12 |
| InChIKey | JWJOTENAMICLJG-QWBYCMEYSA-N |
| PubChem CID | 6918296 |
| ChEMBL | CHEMBL1200969 |
| ChEBI | CHEBI:521033 |
| EC No. | 638-758-5 |
| DTXSID | DTXSID8046452 |
Chemische & physikalische Eigenschaften
| XLogP | 5,4 |
|---|---|
| Polarare Oberfläche (TPSA) | 58,2 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 37 |
| Formalladung | 0 |
| Komplexität | 964 |
| Arzneimittel | Pharmaceuticals -> Genito-urinary system and sex hormones -> UrologicalsPharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 6.8 |
| Löslichkeit | Insoluble9.08e-04 g/LDMSO: soluble2mg/mL, clear |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Schmelzpunkt | 242-250242-250°C |
| Physical Description | Solid |
| Siedepunkt | 620.3±55.0 °C(Predicted) |
| Dichte | 1.303±0.06 g/cm3(Predicted) |
| Lagerbedingungen | -20°C |
| pKa (Säurekonstante) | 13.32±0.70(Predicted) |
| Aggregatzustand | powder |
| Farbe | white to beige |
| BCS Class | 2/4 |
| InChIKey | JWJOTENAMICLJG-QWBYCMEYSA-N |
| SMILES | N1[C@@]2([H])[C@@](C)([C@@]3([H])CC[C@@]4(C)[C@]([H])([C@]3([H])CC2)CC[C@@H]4C(NC2=CC(C(F)(F)F)=CC=C2C(F)(F)F)=O)C=CC1=O |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH351 (15.8%): Suspected of causing cancer [Warning Carcinogenicity]P203, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 19 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Dutusteride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazard Classes and Categories | Carc. 2 (15.8%) |
| Hepatotoxicity | Dutasteride has been associated with a low rate of serum aminotransferase elevations that, in controlled trials, was no higher than with placebo therapy. These elevations were transient and rarely required dose modification. There have been no published reports of clinically apparent liver injury due to dutasteride therapy. |
| Unerwünschte Wirkungen | Adverse Drug Reactions |
| Toxizitätsübersicht | Signs and Symptoms of Overdose |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)DutasteridevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| EPA Human Health Benchmarks for Pharmaceuticals | Dutasteride0.010.05The recommended dose of dutasteride capsules is 1 capsule (0.5 mg dutasteride) taken once daily.Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 0.5 mg/day, Lowest Therapeutic Dose (LTD): 0.006 mg/kg-day, and Screening Dose: 0.000002 mg/kg-day.25-Feb-20 |
| Wassergefährdungsklasse (WGK) | WGK 3 |
| Zollcode | 2937290000 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrenklasse | Carc. 2Repr. 1B |
Anwendungen & Verwendung
Beschreibung
Dutasteride is a synthetic 4-azasteroid compound. It is a dual inhibitor of type 1 and 2 isoforms of 5α-reductase unlike finasteride, the first marketed 5α-reductase inhibitor, which only acts on type 2 isozyme. Dutasteride is a 3-fold greater inhibitor of type-2 5α-reductase than finasteride in men and has greater effect on the type-l than on type-2 isozyme. In animal models,dutasteride exhibited superior efficacy and pharmacokinetics compared to finasteride. In patients with benign prostate hyperplasia, administration of dutasteride was shown to dose-dependently decrease serum dihydrotestosterone levels with greater efficacy as compared to finasteride (95% vs 67%). Serum testosterone levels increased with both active drugs, in conjunction with dihydrotestosterone suppression but remained within normal ranges. In long term studies, in men with moderate to severe benign prostate hyperplasia, once daily dutasteride significantly reduced prostate volume, reduced the risk of acute urinary retention and surgery by 57% and improved lower urinary tract symptoms and urinary flow measurements.
Verwenden
Dutasteride is a dual inhibitor of 5a-reductase isoenzymes type 1 and 2; structurally related to Finasteride. Dutasteride is used in the treatment of benign prostatic hyperplasia. Dutasteride is associated with a low rate of transient serum aminotransferase elevations, but has yet to be linked to instances of clinically apparent acute liver injury.