Epristeride

Base Information

• Chemical Name: Epristeride
• CAS No.: 119169-78-7
• Molecular Formula: C25H37NO3
• Molecular Weight: 399.574
• UNII: 39517A04PS
• DSSTox Substance ID: DTXSID9048643
• Nikkaji Number: J274.922J
• Wikipedia: Epristeride
• Wikidata: Q5383934
• NCI Thesaurus Code: C81621
• Pharos Ligand ID: L2FUHQ6KTG7T
• ChEMBL ID: CHEMBL138225
• Mol file: 119169-78-7.mol

Synonyms:17-N-t-butylcarboxamide androst-3,5-diene-3-carboxylic acid;epristeride;ONO 9302;ONO-9302;SK and F 105657;SK and F-105657;SKF 105657

Chemical Property of Epristeride

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 242-249°
• Refractive Index: 1.563
• Boiling Point: 596°Cat760mmHg
• PKA: 4.8(at 25℃)
• Flash Point: 314.3°C
• PSA: 66.40000
• Density: 1.13g/cm³
• LogP: 5.49190
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 399.27734404
• Heavy Atom Count: 29
• Complexity: 788

Purity/Quality:

98%,99%, ^*data from raw suppliers

Epristeride 99.96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)NC(C)(C)C)CC=C4C3(CCC(=C4)C(=O)O)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC(C)(C)C)CC=C4[C@@]3(CCC(=C4)C(=O)O)C
• Uses: Inhibitor (alpha reductase.

Technology Process of Epristeride

There total 16 articles about Epristeride 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: 77.0%

carbon monoxide (201230-82-2) + 3-Bromo-N-(1,1-dimethylethyl)androsta-3,5-diene-17β-carboxamide (119169-84-5) → epristeride (119169-78-7)

Guidance literature:

With sodium hydroxide; cetyltrimethylammonim bromide; palladium diacetate; triphenylphosphine; In pentan-1-ol; at 80 ℃; for 18h; under 760 Torr;

DOI:10.1080/00397919808006865

Reference yield: 73.5%

3-Carbomethoxy-N-t-butyl-androst-3,5-diene-17β-carboxamide (119169-79-8) → epristeride (119169-78-7)

Guidance literature:

With sodium carbonate; In methanol; water; for 8h; Reflux; Large scale;

Reference yield: 70.0%

carbon monoxide (201230-82-2) + 1,1,2,2-Tetrafluoro-2-(1,1,2,2-tetrafluoro-ethoxy)-ethanesulfonic acid (8S,9S,10R,13S,14S,17S)-17-tert-butylcarbamoyl-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester (174673-05-3) → epristeride (119169-78-7)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In N,N-dimethyl-formamide; at 70 ℃; for 2h;

DOI:10.1016/S0960-894X(98)00339-4

upstream raw materials:

3-Carbomethoxy-N-t-butyl-androst-3,5-diene-17β-carboxamide

carbon dioxide

3-Bromo-N-(1,1-dimethylethyl)androsta-3,5-diene-17β-carboxamide

carbon monoxide

Refernces

• 1、 Tian, Weisheng,Zhu, Zheng,Liao, Qingjiang,Wu, Yikang. "A practical synthesis of 3-substituted Δ(3,6(6))-steroids as new potential 5α-reductase inhibitor". . p. 1949 - 1952. Retrieved 1998.
• 2、 Holt, Dennis A.,Levy, Mark A.,Oh, Hye-Ja,Erb, Jill M.,Heaslip, Julie I.,et al.. "Inhibition of Steroid 5α-Reductase by Unsaturated 3-Carboxysteroids". . p. 943 - 950. Retrieved 1990.
• 3、 -. "Nitrate prodrugs able to release nitric oxide in a controlled and selective way and their use for prevention and treatment of inflammatory, ischemic and proliferative diseases". . . Retrieved 2008/06/13.