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U-69,593

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Chemical compound

Pharmaceutical compound

U-69,593
Clinical data

ATC code	none
Identifiers
IUPAC name N-methyl-2-phenyl-N-[(5R,7S,8S)-7-(pyrrolidin-1-yl)-1-oxaspiro[4.5]dec-8-yl]acetamide
CAS Number	96744-75-1
PubChemCID	105104
IUPHAR/BPS	1655
ChemSpider	94828
UNII	J5S4K6TKTG
ChEBI	CHEBI:73357^Y
ChEMBL	ChEMBL440765
CompTox Dashboard(EPA)	DTXSID3046326
Chemical and physical data
Formula	C₂₂H₃₂N₂O₂
Molar mass	356.510 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(N([C@H]3CC[C@]1(OCCC1)C[C@@H]3N2CCCC2)C)Cc4ccccc4

U-69,593 is adrug which acts as apotent andselective κ₁-opioid receptor agonist.^[1]^[2]^[3] In animal studies it has been shown to produceantinociception,^[1]^[4]^[5]anti-inflammation,^[6]anxiolysis (at low doses),^[7]^[8]^[9]respiratory depression,^[5] anddiuresis,^[10] while having little effect ongastrointestinal motility.^[1] It also inhibits theperipheral, though notcentral secretion ofoxytocin andvasopressin in rats.^[11]^[12]

References

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^^a ^b ^cLa Regina A, Petrillo P, Sbacchi M, Tavani A (1988). "Interaction of U-69,593 with mu-, alpha- and kappa-opioid binding sites and its analgesic and intestinal effects in rats".Life Sciences.42 (3):293–301.doi:10.1016/0024-3205(88)90638-8.PMID 2826959.
^Frey HH (March 1988). "Effect of mu- and kappa-opioid agonists on the electroconvulsive seizure threshold in mice and antagonism by naloxone and MR 2266".Pharmacology & Toxicology.62 (3):150–4.doi:10.1111/j.1600-0773.1988.tb01863.x.PMID 2836842.
^Zukin RS, Eghbali M, Olive D, Unterwald EM, Tempel A (June 1988)."Characterization and visualization of rat and guinea pig brain kappa opioid receptors: evidence for kappa 1 and kappa 2 opioid receptors".Proceedings of the National Academy of Sciences of the United States of America.85 (11):4061–5.Bibcode:1988PNAS...85.4061Z.doi:10.1073/pnas.85.11.4061.PMC 280361.PMID 2836869.
^Millan MJ, Członkowski A, Lipkowski A, Herz A (October 1989)."Kappa-opioid receptor-mediated antinociception in the rat. II. Supraspinal in addition to spinal sites of action".The Journal of Pharmacology and Experimental Therapeutics.251 (1):342–50.doi:10.1016/S0022-3565(25)20726-1.PMID 2571723.
^^a ^bFrance CP, Medzihradsky F, Woods JH (January 1994)."Comparison of kappa opioids in rhesus monkeys: behavioral effects and receptor binding affinities".The Journal of Pharmacology and Experimental Therapeutics.268 (1):47–58.doi:10.1016/S0022-3565(25)38497-1.PMID 8301589.
^Binder W, Machelska H, Mousa S, et al. (June 2001)."Analgesic and antiinflammatory effects of two novel kappa-opioid peptides".Anesthesiology.94 (6):1034–44.doi:10.1097/00000542-200106000-00018.PMID 11465595.S2CID 46531607.
^Privette TH, Terrian DM (April 1995). "Kappa opioid agonists produce anxiolytic-like behavior on the elevated plus-maze".Psychopharmacology.118 (4):444–50.doi:10.1007/BF02245945.PMID 7568631.S2CID 21326960.
^Wall PM, Messier C (February 2000). "U-69,593 microinjection in the infralimbic cortex reduces anxiety and enhances spontaneous alternation memory in mice".Brain Research.856 (1–2):259–80.doi:10.1016/S0006-8993(99)01990-3.PMID 10677636.S2CID 11630212.
^Wall PM, Messier C (May 2000). "Concurrent modulation of anxiety and memory".Behavioural Brain Research.109 (2):229–41.doi:10.1016/S0166-4328(99)00177-1.PMID 10762693.S2CID 42974528.
^Soulard CD, Guerif S, Payne A, Dahl SG (December 1996)."Differential effects of fedotozine compared to other kappa agonists on diuresis in rats".The Journal of Pharmacology and Experimental Therapeutics.279 (3):1379–85.doi:10.1016/S0022-3565(25)21298-8.PMID 8968362.
^Van de Heijning BJ, Koekkoek-Van den Herik I, Van Wimersma Greidanus TB (December 1991). "The opioid receptor subtypes mu and kappa, but not delta, are involved in the control of the vasopressin and oxytocin release in the rat".European Journal of Pharmacology.209 (3):199–206.doi:10.1016/0014-2999(91)90170-U.PMID 1665795.
^Melis MR, Stancampiano R, Gessa GL, Argiolas A (January 1992). "Prevention by morphine of apomorphine- and oxytocin-induced penile erection and yawning: site of action in the brain".Neuropsychopharmacology.6 (1):17–21.PMID 1315136.