HS665

HS665
Clinical data
Other names	HS-665
Drug class	κ-Opioid receptor agonist; Analgesic
Identifiers
	IUPAC name 3-[2-[cyclobutylmethyl(2-phenylethyl)amino]ethyl]phenol;
CAS Number	1409931-92-5;
PubChem CID	71452041;
ChemSpider	28666556;
ChEMBL	ChEMBL2180639;
CompTox Dashboard (EPA)	DTXSID401336626 ;
Chemical and physical data
Formula	C21H27NO
Molar mass	309.453 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC(C1)CN(CCC2=CC=CC=C2)CCC3=CC(=CC=C3)O;
	InChI InChI=1S/C21H27NO/c23-21-11-5-8-19(16-21)13-15-22(17-20-9-4-10-20)14-12-18-6-2-1-3-7-18/h1-3,5-8,11,16,20,23H,4,9-10,12-15,17H2; Key:YNVKFHIWFDRVNY-UHFFFAOYSA-N;

HS665 is a drug which acts as a potent and selective κ-opioid receptor agonist, and has analgesic effects in animal studies.^[1]^[2]^[3]^[4] HS665 is not an agonist for the μ-opioid receptor, leading to less potential for misuse.^[5]

The structure of HS665 is a close analog of an existing compound called RU-24213. RU-24213 has D2-agonist and KOR antagonist pharmacology.^[6]

References

↑ Spetea M, Berzetei-Gurske IP, Guerrieri E, Schmidhammer H (November 2012). "Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective κ opioid receptor agonist". Journal of Medicinal Chemistry. 55 (22): 10302–10306. doi:10.1021/jm301258w. PMID 23134120.
↑ Spetea M, Eans SO, Ganno ML, Lantero A, Mairegger M, Toll L, et al. (August 2017). "Selective κ receptor partial agonist HS666 produces potent antinociception without inducing aversion after i.c.v. administration in mice". British Journal of Pharmacology. 174 (15): 2444–2456. doi:10.1111/bph.13854. PMC 5513865. PMID 28494108.
↑ Erli F, Guerrieri E, Ben Haddou T, Lantero A, Mairegger M, Schmidhammer H, Spetea M (September 2017). "Highly Potent and Selective New Diphenethylamines Interacting with the κ-Opioid Receptor: Synthesis, Pharmacology, and Structure-Activity Relationships". Journal of Medicinal Chemistry. 60 (17): 7579–7590. doi:10.1021/acs.jmedchem.7b00981. PMC 5601360. PMID 28825813.
↑ Zhu L, Cui Z, Zhu Q, Zha X, Xu Y (2018). "Novel Opioid Receptor Agonists with Reduced Morphine-like Side Effects". Mini Reviews in Medicinal Chemistry. 18 (19): 1603–1610. doi:10.2174/1389557518666180716124336. PMID 30009707. S2CID 51628100.
↑ Advokat CD, Comaty JE, Julien RM (2019). Julien's Primer of Drug Action: A comprehensive guide to the actions, uses, and side effects of psychoactive drugs (14th ed.). New York: Worth Publishers. p. 564. ISBN 978-1-319-20054-1.
↑ Fortin M, Degryse M, Petit F, Hunt PF. The dopamine D2 agonists RU 24213 and RU 24926 are also kappa-opioid receptor antagonists. Neuropharmacology. 1991 Apr;30(4):409-12. doi: 10.1016/0028-3908(91)90068-m. PMID: 1677169.

External links

HS665 - Isomer Design

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[1] Spetea M, Berzetei-Gurske IP, Guerrieri E, Schmidhammer H (November 2012). "Discovery and pharmacological evaluation of a diphenethylamine derivative (HS665), a highly potent and selective κ opioid receptor agonist". Journal of Medicinal Chemistry. 55 (22): 10302–10306. doi:10.1021/jm301258w. PMID 23134120.

[2] Spetea M, Eans SO, Ganno ML, Lantero A, Mairegger M, Toll L, et al. (August 2017). "Selective κ receptor partial agonist HS666 produces potent antinociception without inducing aversion after i.c.v. administration in mice". British Journal of Pharmacology. 174 (15): 2444–2456. doi:10.1111/bph.13854. PMC 5513865. PMID 28494108.

[3] Erli F, Guerrieri E, Ben Haddou T, Lantero A, Mairegger M, Schmidhammer H, Spetea M (September 2017). "Highly Potent and Selective New Diphenethylamines Interacting with the κ-Opioid Receptor: Synthesis, Pharmacology, and Structure-Activity Relationships". Journal of Medicinal Chemistry. 60 (17): 7579–7590. doi:10.1021/acs.jmedchem.7b00981. PMC 5601360. PMID 28825813.

[4] Zhu L, Cui Z, Zhu Q, Zha X, Xu Y (2018). "Novel Opioid Receptor Agonists with Reduced Morphine-like Side Effects". Mini Reviews in Medicinal Chemistry. 18 (19): 1603–1610. doi:10.2174/1389557518666180716124336. PMID 30009707. S2CID 51628100.

[5] Advokat CD, Comaty JE, Julien RM (2019). Julien's Primer of Drug Action: A comprehensive guide to the actions, uses, and side effects of psychoactive drugs (14th ed.). New York: Worth Publishers. p. 564. ISBN 978-1-319-20054-1.

[6] Fortin M, Degryse M, Petit F, Hunt PF. The dopamine D2 agonists RU 24213 and RU 24926 are also kappa-opioid receptor antagonists. Neuropharmacology. 1991 Apr;30(4):409-12. doi: 10.1016/0028-3908(91)90068-m. PMID: 1677169.

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