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GR-89696

GR-89696
Identifiers
  • methyl 4-[2-(3,4-dichlorophenyl)acetyl]-3-(pyrrolidin-1-ylmethyl)piperazine-1-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC19H25Cl2N3O3
Molar mass414.33 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1Cl)CC(=O)N2CCN(C(=O)OC)CC2CN3CCCC3
  • InChI=1S/C19H25Cl2N3O3/c1-27-19(26)23-8-9-24(15(13-23)12-22-6-2-3-7-22)18(25)11-14-4-5-16(20)17(21)10-14/h4-5,10,15H,2-3,6-9,11-13H2,1H3
  • Key:HJUAKZYKCANOOZ-UHFFFAOYSA-N
 ☒NcheckY (what is this?)  (verify)

GR-89696 is a drug which acts as a highly selective κ-opioid agonist.[1] It has been studied in various animal species, and has been described as selective for the κ2 subtype.[2][3][4] Recent studies have suggested that GR-89696 and related κ2-selective agonists may be useful for preventing the itching which is a common side effect of conventional opioid analgesic drugs, without the additional side effects of non-selective kappa agonists.[5] The structure bound to the κ-opioid receptor has been reported.[6]

References

  1. ^ Naylor A, Judd DB, Lloyd JE, Scopes DI, Hayes AG, Birch PJ (July 1993). "A potent new class of kappa-receptor agonist: 4-substituted 1-(arylacetyl)-2-[(dialkylamino)methyl]piperazines". Journal of Medicinal Chemistry. 36 (15): 2075–2083. doi:10.1021/jm00067a004. PMID 8393489.
  2. ^ Herrero JF, Headley PM (September 1993). "Functional evidence for multiple receptor activation by kappa-ligands in the inhibition of spinal nociceptive reflexes in the rat". British Journal of Pharmacology. 110 (1): 303–309. doi:10.1111/j.1476-5381.1993.tb13809.x. PMC 2176008. PMID 8220893.
  3. ^ Ho J, Mannes AJ, Dubner R, Caudle RM (April 1997). "Putative kappa-2 opioid agonists are antihyperalgesic in a rat model of inflammation". The Journal of Pharmacology and Experimental Therapeutics. 281 (1): 136–141. PMID 9103490.
  4. ^ Butelman ER, Ko MC, Traynor JR, Vivian JA, Kreek MJ, Woods JH (September 2001). "GR89,696: a potent kappa-opioid agonist with subtype selectivity in rhesus monkeys". The Journal of Pharmacology and Experimental Therapeutics. 298 (3): 1049–1059. PMID 11504802.
  5. ^ Ko MC, Husbands SM (January 2009). "Effects of atypical kappa-opioid receptor agonists on intrathecal morphine-induced itch and analgesia in primates". The Journal of Pharmacology and Experimental Therapeutics. 328 (1): 193–200. doi:10.1124/jpet.108.143925. PMC 2719014. PMID 18842704.
  6. ^ Han J, Zhang J, Nazarova AL, Bernhard SM, Krumm BE, Zhao L, et al. (May 2023). "Ligand and G-protein selectivity in the κ-opioid receptor". Nature. 617 (7960): 417–425. Bibcode:2023Natur.617..417H. doi:10.1038/s41586-023-06030-7. PMC 10172140. PMID 37138078.


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