Galeterone

Base Information

• Chemical Name: Galeterone
• CAS No.: 851983-85-2
• Molecular Formula: C26H32N2O
• Molecular Weight: 388.553
• European Community (EC) Number: 806-537-4
• UNII: WA33E149SW
• DSSTox Substance ID: DTXSID101025602
• Nikkaji Number: J2.952.671K
• Wikipedia: Galeterone
• Wikidata: Q5518498
• NCI Thesaurus Code: C84866
• Pharos Ligand ID: FDNMMW5DDY8D
• Metabolomics Workbench ID: 153406
• ChEMBL ID: CHEMBL2105738
• Mol file: 851983-85-2.mol

Synonyms:17-(1H-benzimidazol-1-yl)androsta-5,16-dien-3beta-ol;3-hydroxy-17-(1H-benzimidazole-1-yl)androsta-5,16-diene;galeterone;VN-124-1

Chemical Property of Galeterone

Chemical Property:

• Melting Point: 189-190 °C
• Boiling Point: 564.5 °C at 760 mmHg
• PKA: 14.71±0.70(Predicted)
• Flash Point: 295.2 °C
• PSA: 38.05000
• Density: 1.28 g/cm³
• LogP: 5.81080
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Aceatae (Slightly, Heated)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 388.251463648
• Heavy Atom Count: 29
• Complexity: 743

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

Galeterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1=CCC3C2CCC4(C3CC=C4N5C=NC6=CC=CC=C65)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](CC1=CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC=C4N5C=NC6=CC=CC=C65)C)O
• Recent ClinicalTrials: 1911GCCC: Galeterone or Galeterone With Gemcitabine for Patients With Metastatic Pancreatic Adenocarcinoma
• Recent EU Clinical Trials: ARMOR3-SV: A Phase 3, Randomized, Open-Label, Multi-Center, Controlled Study of Galeterone Compared with Enzalutamide in Men Expressing Androgen Receptor Splice Variant-7 mRNA with Metastatic Castration Resistant Prostate Cancer
• Description: Galeterone (TOK-001) is a small molecule oral drug that disrupts AR signaling by a novel triple mechanism: it potently and selectively inhibits CYP17 lyase, potently antagonizes AR and decreases AR protein levels (wild-type and mutant), leading to antitumor activity. Galeterone has shown significant anti-tumour activity with a well-tolerated safety profile in patients with CRPC in phase I and II clinical studies.
• Uses: Galeterone is an androgen receptor antagonist and CYP17A1 enzyme inhibitor. It has been used in trials studying the treatment of Prostate Cancer.

Technology Process of Galeterone

There total 5 articles about Galeterone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

3β-acetoxy-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene (851895-79-9) → Galeterone (851983-85-2)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃; for 1.5h;

DOI:10.1021/jm040202w

Reference yield:

3-β-acetoxy-17-(1H-benzimidazol-1-yl)-16-formyl-androsta-5,16-diene (851895-78-8) → Galeterone (851983-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 73.8 percent / Pd/C; benzonitrile / 5 h / Heating

2: 94 percent / KOH / methanol / 1.5 h / 20 °C

With potassium hydroxide; palladium on activated charcoal; benzonitrile; In methanol;

DOI:10.1021/jm040202w

Reference yield:

benzoimidazole (51-17-2,79351-71-6) → Galeterone (851983-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 88.7 percent / K₂CO₃ / dimethylformamide / 1.5 h / 80 °C

2: 73.8 percent / Pd/C; benzonitrile / 5 h / Heating

3: 94 percent / KOH / methanol / 1.5 h / 20 °C

With potassium hydroxide; palladium on activated charcoal; potassium carbonate; benzonitrile; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm040202w

upstream raw materials:

3β-acetoxy-17-(1H-benzimidazol-1-yl)-androsta-5,16-diene

3-β-acetoxy-17-(1H-benzimidazol-1-yl)-16-formyl-androsta-5,16-diene

benzoimidazole

3β-acetoxy-17-chloro-16-formylandrost-5,16-diene

Downstream raw materials:

3β-amino-17-(1H-benzimidazole-1-yl)androsta-5,16-diene

17-benzimidazol-1-yl-androsta-3,5,16-triene

Refernces

• 1、 -. "NOVEL COMPOSITIONS AND METHODS FOR TREATING PROSTATE CANCER". Paragraph 0251; 0252. . Retrieved 2016/03/05.
• 2、 -. "BIOMARKERS FOR TREATMENT OF NEOPLASTIC DISORDERS USING ANDROGEN-TARGETED THERAPIES". Page/Page column 00113. . Retrieved 2015/02/25.