(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide

Base Information

• Chemical Name: (1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
• CAS No.: 98319-26-7
• Molecular Formula: C₂₃H₃₆N₂O₂
• Molecular Weight: 372.551
• Hs Code.: 29379000
• NSC Number: 759318
• Wikidata: Q27163705
• Mol file: 98319-26-7.mol

Synonyms:(1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide;Finasteride, 3;SCHEMBL12194743;BDBM92326;CHEBI:91906;DBEPLOCGEIEOCV-BYQKQGHSSA-N;HMS2094C21;Pharmakon1600-01506069;NSC759318;CCG-213608;SBI-0206935.P001;F0675;AB01563141_01;EN300-27023267;BRD-A83081521-001-01-5;Q27163705;N-(tert-Butyl)-3-oxo-4-aza-5.alpha.-androst-1-ene-17-carboxamide;(4aR,6aS,7S)-N-tert-butyl-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-tert-Butyl-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 (1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 253 °C
• Refractive Index: 1.524
• Boiling Point: 576.6 °C at 760 mmHg
• PKA: 14.17±0.70(Predicted)
• Flash Point: 177.4 °C
• PSA: 58.20000
• Density: 1.065 g/cm³
• LogP: 4.53420
• Storage Temp.: Store at RT
• Solubility.: DMSO: 32 mg/mL, soluble
• Water Solubility.: insoluble
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 372.277678395
• Heavy Atom Count: 27
• Complexity: 678

Purity/Quality:

99% ^*data from raw suppliers

Finasteride ≥98% (HPLC), powder ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T,Xi
• Hazard Codes: Xn,T,Xi
• Statements: 22-61-60-36/37/38
• Safety Statements: 36/37/39-45-53-36-26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)NC(C)(C)C)CCC4C3(C=CC(=O)N4)C
• Isomeric SMILES: C[C@]12CCC3C(C1CC[C@@H]2C(=O)NC(C)(C)C)CCC4[C@@]3(C=CC(=O)N4)C
• Mechanism of Action: Finasteride is a selective inhibitor of the enzyme 5-alpha reductase. It inhibits the conversion of testosterone into dihydrotestosterone (DHT), thereby reducing prostate volume and serum prostate-specific antigen (PSA) levels. By inhibiting androgen activity in the prostate, it has been hypothesized to reduce the risk of prostate cancer development.
• Medical Uses: Finasteride is FDA-approved for the treatment of androgenetic alopecia (AGA) in males. It is also used off-label for female pattern hair loss (FPHL).; Topical formulations of finasteride have been developed to minimize systemic adverse effects associated with oral administration.
• Clinical Efficacy: Oral finasteride has demonstrated efficacy in treating AGA, with studies showing slower progression of hair loss or enhanced hair growth compared to baseline or placebo. Long-term studies have shown sustained benefits of oral finasteride over 5-10 years of treatment. While generally well-tolerated, some patients may experience sexual adverse effects and an increased risk of depression.
• Topical Administration: Topical administration of finasteride offers the potential to reduce systemic adverse effects by targeting 5-alpha reductase specifically in the scalp. This approach aims to maintain efficacy in treating AGA while minimizing the risk of systemic adverse effects.
• Potential Risks and Concerns: There are emerging concerns about the long-lasting pathophysiological harm associated with finasteride use, particularly regarding its potential to cause depression, anxiety, and sexual dysfunction. Organizations such as the Post-Finasteride Syndrome Foundation have been established to address these concerns and provide support for affected individuals.

Technology Process of (1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide

There total 36 articles about (1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide 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: 93.0%

dihydrofinasteride iodide → finasteride (98319-26-7,140375-21-9,140375-22-0)

Guidance literature:

With Oxone; sodium hydrogencarbonate; In methanol; water; at 30 ℃; Solvent;

Reference yield: 90.0%

17β-(N-tert-butylcarbamoyl)-4-aza-5α-androst-1-ene-3-one solvate → finasteride (98319-26-7,140375-21-9,140375-22-0)

Guidance literature:

In water; at 20 ℃; for 4h;

DOI:10.1515/HC.2007.13.2-3.121

Reference yield: 88.0%

17β-(N-tert-butyl-carbamoyl)-4-benzoyl-4-aza-5α-androst-1-ene-3-one → finasteride (98319-26-7,140375-21-9,140375-22-0)

Guidance literature:

With ethylamine; In ethanol; at 25 - 30 ℃; for 12h;

DOI:10.1002/jhet.5570440323

upstream raw materials:

(4aR,4bS,6aS,7S,9aS,9bS,11aR)-7-(Imidazole-1-carbonyl)-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-indeno[5,4-f]quinolin-2-one

dihydro-finasteride

4-aza-androst-5,16-diene-17-cyano-3-one

4-aza-5-androstene-17α-hydroxy-17β-cyano-3-one

Downstream raw materials:

3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid

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

6α-hydroxy-finasteride

Refernces

• 1、 -. "Method for forming double bonds between 1-position and 2-position during synthesis of finasteride and dutasteride". . . Retrieved 2016/12/01.
• 2、 Bhattacharya, Apurba,Manudhane, Kushal S,Maddula, Srinivasula Reddy,Sreekanth,Thota, Sridhar,Bandichhor, Rakeshwar. "Crystallization engineering in aza-steroid: Application in the development of finasteride". . p. 599 - 602. Retrieved 2013/06/05.