Trilostane

Base Information

• Chemical Name: Trilostane
• CAS No.: 13647-35-3
• Deprecated CAS: 27107-98-8,28414-46-2
• Molecular Formula: C₂₀H₂₇NO₃
• Molecular Weight: 329.439
• Hs Code.: 29372900
• European Community (EC) Number: 237-133-0
• UNII: L0FPV48Q5R
• DSSTox Substance ID: DTXSID9023706
• Nikkaji Number: J108.016D
• Wikipedia: Trilostane
• Wikidata: Q907313
• NCI Thesaurus Code: C1263
• RXCUI: 38668
• Pharos Ligand ID: 4BK6B8JNKQNX
• Metabolomics Workbench ID: 43337
• ChEMBL ID: CHEMBL1200907
• Mol file: 13647-35-3.mol

Synonyms:4alpha,5-epoxy-17beta-hydroxy-3-oxoandrostane-2-carbonitrile;Modrenal;trilostane;WIN 24,540

Chemical Property of Trilostane

Chemical Property:

• Appearance/Colour: tan crystals
• Vapor Pressure: 5.39E-12mmHg at 25°C
• Melting Point: 264 °C
• Refractive Index: 1.61
• Boiling Point: 497.8 °C at 760 mmHg
• PKA: 8.57±0.70(Predicted)
• Flash Point: 254.8 °C
• PSA: 76.78000
• Density: 1.25 g/cm³
• LogP: 3.46688
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥17mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 329.19909372
• Heavy Atom Count: 24
• Complexity: 692

Purity/Quality:

99.0%min, ^*data from raw suppliers

Trilostane ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-62
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2O)CCC45C3(CC(=C(C4O5)O)C#N)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@]45[C@@]3(CC(=C([C@H]4O5)O)C#N)C
• Recent ClinicalTrials: Randomized Study of Letrozole and Trilostane for Medical Abortion
• Recent EU Clinical Trials: A Phase IV Non-randomised Study of Modrenal? (Trilostane) in
• Indications: Trilostane can inhibit 3β-dehydrogenase in the synthesis of corticosteroids, and decrease the synthesis of cortisol and aldosterone. It also can be used in the treatment of Cushing's syndrome (hypercortisolism) and primary aldosteronism. But the efficacy to treat Cushing's syndrome (hypercortisolism) is not as metyrapone. This product also has a significant role in lowering blood testosterone levels, which may be related with that its synthesis is inhibited.
• Description: 3β-hydroxysteroid dehydrogenase (3β-HSD) type 1 and type 2 isoforms are key enzymes for the biosynthesis of all active steroid hormones. 3β-HSD1 (type I) is expressed in placenta and peripheral tissues including breast tumors, whereas 3β-HSD2 (type 2) is expressed in the adrenal gland, ovary, and testis. Trilostane is an inhibitor of the 3β-HSDs: 3β-HSD1 and 3β-HSD2 with Ki values of 0.10 and 1.60 μM, respectively. Trilsotane has been approved for use in the treatment of Cushing’s syndrome in dogs to reduce cortisol, aldosterone, and corticosterone levels. Because human 3β-HSD (type 1) is a critical enzyme in the conversion of DHEA to estradiol in breast tumors, trilostane is also of interest for the treatment of breast cancer in postmenopausal women.
• Uses: An inhibitor of steroid biosynthesis. Used as an adrenocortical suppressant. Used in the treatment of breast cancer. An inhibitor of steroid biosynthesis. Used as an adrenocortical suppressant. Used in the treatment of breast cancer Trilostane has been used to evaluate its capability to regulate the sex-dependent differences in the lipopolysaccharide (LPS)-induced inflammatory responses of astrocytes.
• Therapeutic Function: Corticosteroid antagonist

Technology Process of Trilostane

There total 1 articles about Trilostane 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: 95.0%

4α,5-epoxy-(5α)-androstano[2,3-d]isoxazol-17β-ol (20051-76-7) → Trilostane (13647-35-3)

Guidance literature:

4α,5-epoxy-(5α)-androstano[2,3-d]isoxazol-17β-ol; With sodium hydroxide; In methanol; at 40 - 45 ℃; for 2h;

With acetic acid; In methanol; water; at 40 - 45 ℃; for 2h;

upstream raw materials:

4α,5-epoxy-(5α)-androstano[2,3-d]isoxazol-17β-ol

Refernces