Literature DB >> 31223461

Discovery of SHR1653, a Highly Potent and Selective OTR Antagonist with Improved Blood-Brain Barrier Penetration.

Xin Li1, Zhigao Zhang1, Yang Chen1, Hong Wan1, Jiakang Sun1, Bin Wang1, Bingqiang Feng1, Bing Hu1, Xingxing Shi1, Jun Feng1, Lei Zhang1, Feng He1,2, Chang Bai1, Lianshan Zhang3, Weikang Tao1,2.   

Abstract

The oxytocin receptor (OTR) plays a major role in the control of male sexual responses. Antagonists of the OTR have been reported to inhibit ejaculation in animal models and serve as a potential treatment for premature ejaculation (PE). Herein, we describe a novel scaffold featuring an aryl substituted 3-azabicyclo [3.1.0] hexane structure. The lead compound, SHR1653, was shown to be a highly potent OTR antagonist, which exhibited excellent selectivity over V1AR, V1BR, and V2R. This novel molecule was shown to have a favorable pharmacokinetic profile across species, as well as robust in vivo efficacy in a rat uterine contraction model. Interestingly, SHR1653 exhibited excellent blood-brain barrier penetration, which might be beneficial for the treatment of CNS-related PE.

Entities:  

Year:  2019        PMID: 31223461      PMCID: PMC6580551          DOI: 10.1021/acsmedchemlett.9b00186

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN: 1948-5875            Impact factor:   4.345


  17 in total

Review 1.  The oxytocin receptor system: structure, function, and regulation.

Authors:  G Gimpl; F Fahrenholz
Journal:  Physiol Rev       Date:  2001-04       Impact factor: 37.312

Review 2.  The oxytocin receptor.

Authors:  Hans H Zingg; Stephane A Laporte
Journal:  Trends Endocrinol Metab       Date:  2003-07       Impact factor: 12.015

3.  Oral oxytocin antagonists.

Authors:  Alan D Borthwick
Journal:  J Med Chem       Date:  2010-09-23       Impact factor: 7.446

Review 4.  International Society for Sexual Medicine's guidelines for the diagnosis and treatment of premature ejaculation.

Authors:  Stanley E Althof; Carmita H N Abdo; John Dean; Geoff Hackett; Marita McCabe; Chris G McMahon; Raymond C Rosen; Richard Sadovsky; Marcel Waldinger; Edgardo Becher; Gregory A Broderick; Jacques Buvat; Irwin Goldstein; Amr I El-Meliegy; Francois Giuliano; Wayne J G Hellstrom; Luca Incrocci; Emmanuele A Jannini; Kwangsung Park; Sharon Parish; Hartmut Porst; David Rowland; Robert Segraves; Ira Sharlip; Chiara Simonelli; Hui Meng Tan
Journal:  J Sex Med       Date:  2010-09       Impact factor: 3.802

5.  High-throughput screening of drug-brain tissue binding and in silico prediction for assessment of central nervous system drug delivery.

Authors:  Hong Wan; Mikael Rehngren; Fabrizio Giordanetto; Fredrik Bergström; Anders Tunek
Journal:  J Med Chem       Date:  2007-08-29       Impact factor: 7.446

6.  Triazole oxytocin antagonists: identification of aryl ether replacements for a biaryl substituent.

Authors:  Alan Brown; Lindsay Brown; T Bruce Brown; Andrew Calabrese; Dave Ellis; Nicholas Puhalo; Chris R Smith; Olga Wallace; Lesa Watson
Journal:  Bioorg Med Chem Lett       Date:  2008-08-22       Impact factor: 2.823

7.  Pharmacology of (2S,4Z)-N-[(2S)-2-hydroxy-2-phenylethyl]-4-(methoxyimino) -1-[(2'-methyl[1,1'-biphenyl]-4-yl)carbonyl]-2-pyrrolidinecarboxamide, a new potent and selective nonpeptide antagonist of the oxytocin receptor.

Authors:  Rocco Cirillo; Enrico Gillio Tos; Matthias K Schwarz; Anna Quattropani; Alexander Scheer; Marc Missotten; Jerome Dorbais; Anthony Nichols; Francesco Borrelli; Claudio Giachetti; Lucia Golzio; Paolo Marinelli; Russell J Thomas; Claude Chevillard; Florence Laurent; Karine Portet; Claude Barberis; Andre Chollet
Journal:  J Pharmacol Exp Ther       Date:  2003-03-26       Impact factor: 4.030

Review 8.  Oxytocin involvement in SSRI-induced delayed ejaculation: a review of animal studies.

Authors:  Trynke R de Jong; Jan G Veening; Berend Olivier; Marcel D Waldinger
Journal:  J Sex Med       Date:  2007-01       Impact factor: 3.802

9.  Treatment with oxytocin antagonists before embryo transfer may increase implantation rates after IVF.

Authors:  Ozlem Moraloglu; Esra Tonguc; Turgut Var; Tugba Zeyrek; Sertac Batioglu
Journal:  Reprod Biomed Online       Date:  2010-04-18       Impact factor: 3.828

10.  Triazole oxytocin antagonists: Identification of an aryloxyazetidine replacement for a biaryl substituent.

Authors:  Alan Brown; T Bruce Brown; Andrew Calabrese; Dave Ellis; Nicholas Puhalo; Michael Ralph; Lesa Watson
Journal:  Bioorg Med Chem Lett       Date:  2009-11-23       Impact factor: 2.823

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