Spiradoline

Drugbox
IUPAC_name = 2-(3,4-dichlorophenyl)-N-methyl-N- [(5R,7S,8S)-7-pyrrolidin-1-yl-1-oxaspiro [4.5] decan-8-yl] acetamide

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width = 200
CAS_number = 87151-85-7
smiles = CN( [C@H] 1CC [C@@] 2(CCCO2)C [C@@H] 1N3CCCC3)C(=O)CC4=CC(=C(C=C4)Cl)Cl
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PubChem = 55652
DrugBank =
C=22|H=30|Cl=2|N=2|O=2
molecular_weight = 425.392 g/mol
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Spiradoline (U-62066) is a drug which acts as a highly selective κ-opioid agonist. [Vonvoigtlander PF, Lewis RA. Analgesic and mechanistic evaluation of spiradoline, a potent kappa opioid. "Journal of Pharmacology and Experimental Therapeutics". 1988 Jul;246(1):259-62. PMID 2839665] It has analgesic, [Kunihara M, Ohyama M, Nakano M, Hayashi S. Analgesic activity of spiradoline mesylate (U-62,066E), a kappa opioid agonist in mice. "Life Sciences". 1989;45(13):1191-8. PMID 2796604] diuretic [Yamada K, Imai M, Yoshida S. Mechanism of diuretic action of U-62,066E, a kappa opioid receptor agonist. "European Journal of Pharmacology". 1989 Jan 31;160(2):229-37. PMID 2547626] and antitussive effects, [Kamei J, Tanihara H, Kasuya Y. Antitussive effects of two specific kappa-opioid agonists, U-50,488H and U-62,066E, in rats. "European Journal of Pharmacology". 1990 Oct 9;187(2):281-6. PMID 2272363] and produces subjective effects in animals similar to those of ketocyclazocine and allylnormetazocine. [Holtzman SG. Further characterization of the discriminative stimulus effects of spiradoline. "Pharmacology, Biochemistry and Behaviour". 2000 Jul;66(3):517-22. PMID 10899364] The main effect in humans is sedation, along with analgesic and diuretic effects, but significant side effects such as dysphoria and hallucinations have stopped it from being used clinically. [Wadenberg ML. A review of the properties of spiradoline: a potent and selective kappa-opioid receptor agonist. "CNS Drug Reviews". 2003 Summer;9(2):187-98. PMID 12847558]

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