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GR-89696

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Chemical compound

Pharmaceutical compound

GR-89696
Identifiers


IUPAC name methyl 4-[2-(3,4-dichlorophenyl)acetyl]-3-(pyrrolidin-1-ylmethyl)piperazine-1-carboxylate
CAS Number	126766-32-3^Y
PubChemCID	3505
IUPHAR/BPS	1649
ChemSpider	3385
UNII	YDF52K5SDR
ChEMBL	ChEMBL277863^N
PDB ligand	U9I (PDBe,RCSB PDB)
CompTox Dashboard(EPA)	DTXSID50875164
Chemical and physical data
Formula	C₁₉H₂₅Cl₂N₃O₃
Molar mass	414.33 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1Cl)CC(=O)N2CCN(C(=O)OC)CC2CN3CCCC3
InChI 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
^NY (what is this?) (verify)

GR-89696 is a drug which acts as a highly selectiveκ-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 theitching which is a common side effect of conventionalopioid analgesic drugs, without the additional side effects of non-selective kappa agonists.^[5] The structure bound to theκ-opioid receptor has been reported.^[6]

References

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^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.
^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.
^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.doi:10.1016/S0022-3565(24)36556-5.PMID 9103490.
^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.doi:10.1016/S0022-3565(24)29474-X.PMID 11504802.
^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.
^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.