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OJBTm
Online Journal of Bioinformatics
Established 1995

ISSN  1443-2250


Volume 20(3): 233-244, 2019.


Alternate synthesis of Finasteride and derivatives to inhibit 5α-reductase.


Divya Sanganabhatla and R Shyam Sunder.

 

Department of Pharmacy, University College of Technology, Osmania University, Hyderabad-500007, India

 

ABSTRACT

 

Sanganabhatla D, Sunder RS., Alternate synthesis of Finasteride and derivatives to inhibit 5α-reductase,
20(3): 233-244, 2019. Finasteride is used to manage benign prostatic hyperplasia and androgenic alopecia but currently its synthesis is a costly process. We synthesized finasteride (3-oxo-4-aza-5α-androst-1-ene-17β-(N-tert-butylcarboxamide) and its derivatives from 4-androsten-3,17-dione via 7 steps with an overall yield of 20%. Conditions of processing were optimized and scaled by purification of each step by crystallization and recrystallization. At 1st step we obtained ~95% acid 3 compared with previously reported 88.8% by using ~10% less sodium periodate. Hydrogenation was optimized by using 0.2 weight equivalent of palladium carbon atmospheric pressure at 25oC for 4 h to yield 78.2%. We used 2,3-dichloro-5,6-dicyanobenzoquinone to synthesize large amounts of finasteride by re-crystallization of crude product from ethanol to yield 71.1% powder meeting British Pharmacopeia 2007 standards. The products and all intermediates were fully characterized by physical and spectroscopic methods. The overall yield was 20.01%, higher than those reported (16-18%). In synthesis of finasteride, derivatives 3 and 4 showed optimal GOLD In silico docking and inhibition of α-reductase.

 

KEYWORDS: Finasteride, benign prostatic hyperplasia, androst-4-en-3,17-dione, synthesis, Docking.