Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H32N2O2 |
| Molecular Weight | 356.5017 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN([C@H]1CC[C@@]2(CCCO2)C[C@@H]1N3CCCC3)C(=O)CC4=CC=CC=C4
InChI
InChIKey=PGZRDDYTKFZSFR-ONTIZHBOSA-N
InChI=1S/C22H32N2O2/c1-23(21(25)16-18-8-3-2-4-9-18)19-10-12-22(11-7-15-26-22)17-20(19)24-13-5-6-14-24/h2-4,8-9,19-20H,5-7,10-17H2,1H3/t19-,20-,22-/m0/s1
| Molecular Formula | C22H32N2O2 |
| Molecular Weight | 356.5017 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [3H]U-69593 a highly selective ligand for the opioid kappa receptor. | 1985 Feb 26 |
|
| kappa-Opioid receptor in humans: cDNA and genomic cloning, chromosomal assignment, functional expression, pharmacology, and expression pattern in the central nervous system. | 1995 Jul 18 |
|
| Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception. | 1995 Sep |
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| Prevention by morphine of apomorphine- and oxytocin-induced penile erection and yawning: involvement of nitric oxide. | 1997 May |
|
| Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications. | 1998 Mar |
|
| Sensitization of the adenylyl cyclase system in cloned kappa-opioid receptor-transfected cells following sustained agonist treatment: A chimeric study using G protein alpha(i)2/alpha(q) subunits. | 1999 Dec |
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| U69593, a kappa-opioid agonist, decreases cocaine self-administration and decreases cocaine-produced drug-seeking. | 1999 Jun |
|
| G-protein-coupled receptor heterodimerization modulates receptor function. | 1999 Jun 17 |
|
| Kappa-opioid receptor activation prevents alterations in mesocortical dopamine neurotransmission that occur during abstinence from cocaine. | 2000 |
|
| Reinstatement of extinguished drug-taking behavior in rats: effect of the kappa-opioid receptor agonist, U69593. | 2000 Jul |
|
| Effects of the kappa-opioid receptor agonist, U69593, on the development of sensitization and on the maintenance of cocaine self-administration. | 2001 Apr |
|
| Oligomerization of opioid receptors with beta 2-adrenergic receptors: a role in trafficking and mitogen-activated protein kinase activation. | 2001 Jan 2 |
|
| Kappa opioid receptor stimulation decreases amphetamine-induced behavior and neuropeptide mRNA expression in the striatum. | 2001 Sep 10 |
|
| Kappa opioids inhibit physiologically identified medullary pain modulating neurons and reduce morphine antinociception. | 2005 Mar |
|
| Mu- and kappa-opioids induce the differentiation of embryonic stem cells to neural progenitors. | 2006 Nov 3 |
|
| Sex differences in the potency of kappa opioids and mixed-action opioids administered systemically and at the site of inflammation against capsaicin-induced hyperalgesia in rats. | 2007 Apr |
|
| Pharmacological and genetic manipulation of kappa opioid receptors: effects on cocaine- and pentylenetetrazol-induced convulsions and seizure kindling. | 2007 Mar |
|
| Effect of kappa-opioid receptor agonists U69593, U50488H, spiradoline and salvinorin A on cocaine-induced drug-seeking in rats. | 2009 Dec |
|
| Discovery of aminobenzyloxyarylamides as κ opioid receptor selective antagonists: application to preclinical development of a κ opioid receptor antagonist receptor occupancy tracer. | 2011 Dec 8 |
|
| Structural determinants of opioid and NOP receptor activity in derivatives of buprenorphine. | 2011 Oct 13 |
|
| Essential structure of opioid κ receptor agonist nalfurafine for binding to the κ receptor 2: synthesis of decahydro(iminoethano)phenanthrene derivatives and their pharmacologies. | 2012 Aug 1 |
Patents
Sample Use Guides
in rats: in the intestinal transit test U-69,593 at doses between 0.5 and 15 mg/kg i.p. only slightly slowed intestinal transit of a charcoal meal in rats with no dose-relation; it partly but significantly antagonized morphine-induced constipation
Route of Administration:
Intraperitoneal
Receptor binding studies were performed to characterize the properties of subtypes of kappa opioid receptors in membrane preparations of human cerebral cortex. [3H]U69,593 ([3H]U69), a selective kappa 1-agonist, and [3H]diprenorphine ([3H]DIP), a non-selective opioid antagonist, in the presence of 1 microM each of DAMGO, DPDPE and U-69 to block mu-, delta-, and kappa 1-sites, labeled single population of binding sites, respectively. [3H]U-69 binding sites (KD = 3.8 +/- 0.2 nM, Bmax = 6.3 +/- 0.2 fmol/mg protein) had a binding profile that correspond to kappa 1-receptor.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:37:48 GMT 2023
by
admin
on
Fri Dec 15 19:37:48 GMT 2023
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| Record UNII |
J5S4K6TKTG
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| Record Status |
Validated (UNII)
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| Record Version |
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U 69593
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DTXSID3046326
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105104
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LABELED -> NON-LABELED |
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TARGET -> AGONIST |
[35S]-GTPγS Assay Emax
EC50
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ACTIVE MOIETY |
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