Literature DB >> 25147603

Discovery of a Potent Analgesic NOP and Opioid Receptor Agonist: Cebranopadol.

Stefan Schunk1, Klaus Linz1, Claudia Hinze1, Sven Frormann1, Stefan Oberbörsch1, Bernd Sundermann1, Saskia Zemolka1, Werner Englberger1, Tieno Germann1, Thomas Christoph1, Babette-Y Kögel1, Wolfgang Schröder1, Stephanie Harlfinger1, Derek Saunders1, Achim Kless1, Hans Schick2, Helmut Sonnenschein2.   

Abstract

In a previous communication, our efforts leading from 1 to the identification of spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amine 2a as analgesic NOP and opioid receptor agonist were disclosed and their favorable in vitro and in vivo pharmacological properties revealed. We herein report our efforts to further optimize lead 2a, toward trans-6'-fluoro-4',9'-dihydro-N,N-dimethyl-4-phenyl-spiro[cyclohexane-1,1'(3'H)-pyrano[3,4-b]indol]-4-amine (cebranopadol, 3a), which is currently in clinical development for the treatment of severe chronic nociceptive and neuropathic pain.

Entities:  

Keywords:  MOP receptor agonists; NOP receptor agonists; analgesics; cebranopadol

Year:  2014        PMID： 25147603      PMCID： PMC4137374          DOI： 10.1021/ml500117c

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


  13 in total

Review 1.  Opioids.

Authors:  C Zöllner; C Stein
Journal:  Handb Exp Pharmacol       Date:  2007

2.  Discovery of Spiro[cyclohexane-dihydropyrano[3,4-b]indole]-amines as Potent NOP and Opioid Receptor Agonists.

Authors:  Stefan Schunk; Klaus Linz; Sven Frormann; Claudia Hinze; Stefan Oberbörsch; Bernd Sundermann; Saskia Zemolka; Werner Englberger; Tieno Germann; Thomas Christoph; Babette-Y Kögel; Wolfgang Schröder; Stephanie Harlfinger; Derek Saunders; Achim Kless; Hans Schick; Helmut Sonnenschein
Journal:  ACS Med Chem Lett       Date:  2014-06-24       Impact factor: 4.345

3.  In vitro and in vivo characterization of tapentadol metabolites.

Authors:  R Terlinden; B Y Kogel; W Englberger; T M Tzschentke
Journal:  Methods Find Exp Clin Pharmacol       Date:  2010 Jan-Feb

4.  Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches.

Authors:  O P Hamill; A Marty; E Neher; B Sakmann; F J Sigworth
Journal:  Pflugers Arch       Date:  1981-08       Impact factor: 3.657

5.  Cebranopadol: a novel potent analgesic nociceptin/orphanin FQ peptide and opioid receptor agonist.

Authors:  Klaus Linz; Thomas Christoph; Thomas M Tzschentke; Thomas Koch; Klaus Schiene; Michael Gautrois; Wolfgang Schröder; Babette Y Kögel; Horst Beier; Werner Englberger; Stefan Schunk; Jean De Vry; Ulrich Jahnel; Stefanie Frosch
Journal:  J Pharmacol Exp Ther       Date:  2014-04-08       Impact factor: 4.030

6.  A preclinical comparison between different opioids: antinociceptive versus adverse effects.

Authors:  Theo F Meert; Hilde A Vermeirsch
Journal:  Pharmacol Biochem Behav       Date:  2005-01-07       Impact factor: 3.533

Review 7.  The use of bifunctional NOP/mu and NOP receptor selective compounds for the treatment of pain, drug abuse, and psychiatric disorders.

Authors:  Lawrence Toll
Journal:  Curr Pharm Des       Date:  2013       Impact factor: 3.116

8.  Roles of μ-opioid receptors and nociceptin/orphanin FQ peptide receptors in buprenorphine-induced physiological responses in primates.

Authors:  Colette M Cremeans; Erin Gruley; Donald J Kyle; Mei-Chuan Ko
Journal:  J Pharmacol Exp Ther       Date:  2012-06-28       Impact factor: 4.030

9.  Crystal structure of the µ-opioid receptor bound to a morphinan antagonist.

Authors:  Aashish Manglik; Andrew C Kruse; Tong Sun Kobilka; Foon Sun Thian; Jesper M Mathiesen; Roger K Sunahara; Leonardo Pardo; William I Weis; Brian K Kobilka; Sébastien Granier
Journal:  Nature       Date:  2012-03-21       Impact factor: 49.962

10.  Structure of the nociceptin/orphanin FQ receptor in complex with a peptide mimetic.

Authors:  Aaron A Thompson; Wei Liu; Eugene Chun; Vsevolod Katritch; Huixian Wu; Eyal Vardy; Xi-Ping Huang; Claudio Trapella; Remo Guerrini; Girolamo Calo; Bryan L Roth; Vadim Cherezov; Raymond C Stevens
Journal:  Nature       Date:  2012-05-16       Impact factor: 49.962
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  27 in total

1.  Structure-Based SAR in the Design of Selective or Bifunctional Nociceptin (NOP) Receptor Agonists.

Authors:  Michael E Meyer; Arpit Doshi; Dennis Yasuda; Nurulain T Zaveri
Journal:  AAPS J       Date:  2021-05-11       Impact factor: 4.009

2.  A bifunctional nociceptin and mu opioid receptor agonist is analgesic without opioid side effects in nonhuman primates.

Authors:  Huiping Ding; Norikazu Kiguchi; Dennis Yasuda; Pankaj R Daga; Willma E Polgar; James J Lu; Paul W Czoty; Shiroh Kishioka; Nurulain T Zaveri; Mei-Chuan Ko
Journal:  Sci Transl Med       Date:  2018-08-29       Impact factor: 17.956

Review 3.  Central N/OFQ-NOP Receptor System in Pain Modulation.

Authors:  Norikazu Kiguchi; Huiping Ding; Mei-Chuan Ko
Journal:  Adv Pharmacol       Date:  2015-12-17

4.  A novel orvinol analog, BU08028, as a safe opioid analgesic without abuse liability in primates.

Authors:  Huiping Ding; Paul W Czoty; Norikazu Kiguchi; Gerta Cami-Kobeci; Devki D Sukhtankar; Michael A Nader; Stephen M Husbands; Mei-Chuan Ko
Journal:  Proc Natl Acad Sci U S A       Date:  2016-08-29       Impact factor: 11.205

5.  Pharmacological studies on the NOP and opioid receptor agonist PWT2-[Dmt1]N/OFQ(1-13).

Authors:  Maria Camilla Cerlesi; Huiping Ding; Mark F Bird; Norikazu Kiguchi; Federica Ferrari; Davide Malfacini; Anna Rizzi; Chiara Ruzza; David G Lambert; Mei-Chuan Ko; Girolamo Calo; Remo Guerrini
Journal:  Eur J Pharmacol       Date:  2016-11-19       Impact factor: 4.432

Review 6.  Nociceptin/Orphanin FQ Peptide Receptor-Related Ligands as Novel Analgesics.

Authors:  Norikazu Kiguchi; Huiping Ding; Shiroh Kishioka; Mei-Chuan Ko
Journal:  Curr Top Med Chem       Date:  2020       Impact factor: 3.295

Review 7.  Nociceptin/Orphanin FQ Receptor Structure, Signaling, Ligands, Functions, and Interactions with Opioid Systems.

Authors:  Lawrence Toll; Michael R Bruchas; Girolamo Calo'; Brian M Cox; Nurulain T Zaveri
Journal:  Pharmacol Rev       Date:  2016-03-08       Impact factor: 25.468

Review 8.  Strategies for Developing κ Opioid Receptor Agonists for the Treatment of Pain with Fewer Side Effects.

Authors:  Kelly F Paton; Diana V Atigari; Sophia Kaska; Thomas Prisinzano; Bronwyn M Kivell
Journal:  J Pharmacol Exp Ther       Date:  2020-09-10       Impact factor: 4.030

9.  Bifunctional Peptide-Based Opioid Agonist-Nociceptin Antagonist Ligands for Dual Treatment of Acute and Neuropathic Pain.

Authors:  Karel Guillemyn; Joanna Starnowska; Camille Lagard; Jolanta Dyniewicz; Ewelina Rojewska; Joanna Mika; Nga N Chung; Valérie Utard; Piotr Kosson; Andrzej W Lipkowski; Lucie Chevillard; Pol Arranz-Gibert; Meritxell Teixidó; Bruno Megarbane; Dirk Tourwé; Frédéric Simonin; Barbara Przewlocka; Peter W Schiller; Steven Ballet
Journal:  J Med Chem       Date:  2016-04-14       Impact factor: 7.446

Review 10.  Medications for substance use disorders (SUD): emerging approaches.

Authors:  Eduardo R Butelman; Mary Jeanne Kreek
Journal:  Expert Opin Emerg Drugs       Date:  2017-10-30       Impact factor: 4.191
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