Pharmakon1600-01505386

Base Information

• Chemical Name: Pharmakon1600-01505386
• CAS No.: 164656-23-9
• Molecular Formula: C₂₇H₃₀F₆N₂O₂
• Molecular Weight: 528.538
• Hs Code.: 2937290000
• NSC Number: 759880
• Pharos Ligand ID: 6F6SUUFRD35T
• ChEMBL ID: CHEMBL283245
• Mol file: 164656-23-9.mol

Synonyms:CHEMBL283245;Pharmakon1600-01505386;SCHEMBL12194984;JWJOTENAMICLJG-JLAOSSPPSA-N;BDBM50057487;NSC759880;EN300-27695465;(1S,9aR,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide;(4aR,6aS,7S)-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-carboxylic acid (2,5-bis-trifluoromethyl-phenyl)-amide;(4aR,6aS,7S)-N-[2,5-bis(trifluoromethyl)phenyl]-4a,6a-dimethyl-2-oxo-1H,2H,4aH,4bH,5H,6H,6aH,7H,8H,9H,9aH,9bH,10H,11H,11aH-indeno[5,4-f]quinoline-7-carboxamide;(4aR,6aS,7S)-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

Chemical Property of Pharmakon1600-01505386

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 242-250 °C
• Refractive Index: 1.523
• Boiling Point: 620.3 °C at 760 mmHg
• PKA: 13.32±0.70(Predicted)
• Flash Point: 329 °C
• PSA: 58.20000
• Density: 1.303 g/cm³
• LogP: 6.97790
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: soluble2mg/mL, clear
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 528.22114718
• Heavy Atom Count: 37
• Complexity: 964

Purity/Quality:

99% ^*data from raw suppliers

Dutasteride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CCC5C3(C=CC(=O)N5)C
• Isomeric SMILES: C[C@]12CCC3C(C1CC[C@@H]2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CCC5[C@@]3(C=CC(=O)N5)C
• Description: 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.
• Uses: 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.
• Biological Functions: Similar to finasteride, dutasteride is a competitive and mechanism-based inhibitor not only of type 2 but also of type 1 5α-reductase isoenzymes, with which stable enzyme-NADP adduct complexes are formed, inhibiting the conversion of testosterone to DHT. The suppression of both type 1 and type 2 isoforms results in greater and more consistent reduction of plasma DHT than that observed for finasteride. The more effective dual inhibition of type 1 and type 2 5α-reductase isoforms lowers circulating DHT to a greater extent than with finasteride and shows advantages in treating BPH and other disease states (e.g., prostate cancer) that are DHT-dependent.
• Clinical Use: Dutasteride belongs to azasteriod class of compounds and function as a 5α-reductase inhibitor1 which prevents the conversion of the androgen sex hormone testosterone into the more potent metabolite dihydrotestosterone (DHT). In 2009, South Korea has been licensed dutasteride for the treatment of androgenetic alopecia and in Japan 2015.Dutasteride is the first and only double 5α reductase inhibitor used to treat Benign prostatic hyperplasia, and it is mainly used clinically to treat prostate enlargement, male-pattern hair loss, seborrheic hair loss, and hereditary hair loss.
• Drug interactions: Potentially hazardous interactions with other drugsNone known

Technology Process of Pharmakon1600-01505386

There total 33 articles about Pharmakon1600-01505386 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: 95.2%

2,5-bis(trifluoromethyl)aniline (328-93-8) + (S)-3-keto-4-aza-5α-androstane-1-ene-17β-formyl chloride → (5α,17β)-N-(2,5-bis(trifluoromethyl)phenyl)-3-oxo-4-azaandrost-1-ene-17-carboxamide (1796930-46-5,164656-23-9)

Guidance literature:

With pyridine; In toluene; at 90 ℃; for 3h; Temperature;

Reference yield: 88.21%

2,5-bis(trifluoromethyl)aniline (328-93-8) + 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid (104239-97-6) → dutasteride (1796930-46-5,164656-23-9)

Guidance literature:

2,5-bis(trifluoromethyl)aniline; With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; at 105 - 110 ℃;

3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid; In N,N-dimethyl-formamide;

Reference yield: 82.2%

2,5-bis(trifluoromethyl)aniline (328-93-8) + C23H33NO4 → dutasteride (1796930-46-5,164656-23-9)

Guidance literature:

In tetrahydrofuran; for 3h;

upstream raw materials:

2-iodo-1,4-bis-(trifluoromethyl)-benzene

3-Oxo-4-aza-5alpha-androst-1-ene-17beta-carboxamide

C₂₀H₂₉NO₅S

2,5-bis(trifluoromethyl)aniline

Refernces

• 1、 -. "A method of preparation he male amine". Paragraph 0012-0013. . Retrieved 2018/09/26.
• 2、 -. "A high-pure undistilled he male amine preparation method (by machine translation)". Paragraph 0064. . Retrieved 2017/08/29.