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Old 08-15-2014, 07:00 AM
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rss 3-Alkoxy-pyrrolo[1,2-b]pyrazolines as novel selective androgen receptor modulators (S

Related Articles 3-Alkoxy-pyrrolo[1,2-b]pyrazolines as novel selective androgen receptor modulators (SARMs) with ideal physicochemical properties for transdermal administration.

J Med Chem. 2014 Aug 14;

Authors: Ullrich T, Sasmal S, Boorgu V, Pasagadi S, Cheera S, Rajagopalan S, Bhumireddy A, Shashikumar D, Chelur S, Belliappa C, Pandit C, Krishnamurthy N, Mukherjee S, Ramanathan A, Ghadiyaram C, Ramachandra M, Santos PG, Lagu B, Bock MG, Perrone MH, Weiler S, Keller H

Abstract
We describe the synthesis and characterization of 3-alkoxy-pyrrolo[1,2-b]pyrazolines as novel selective androgen receptor (AR) modulators that possess excellent physicochemical properties for transdermal administration. Compound 26 bound to human AR with an IC50 of 0.7 nM with great selectivity over other nuclear hormone receptors and potently activated AR in a C2C12 muscle cell reporter gene assay with an EC50 of 0.5 nM. It showed high aqueous solubility of 1.3 g/L at pH 7.4 and an in silico model as well as a customized parallel artificial membrane permeability assay indicated good skin permeation. Indeed, when measuring skin permeation through excised human skin an excellent flux of 2 Ķg/(cm(2)*h) was determined without any permeation enhancers. In a two-week Hershberger model using castrated rats, the compound showed dose-dependent effects fully restoring skeletal muscle weight at 0.3 mg/kg/day after subcutaneous administration with high selectivity over prostate stimulation.


PMID: 25121964 [PubMed - as supplied by publisher]



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