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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
Structure of U-69593

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

HIDE SMILES / InChI
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

Description

U-69,593 is a selective κ1-opioid receptor agonist. In the experiments on rats it reverses enhanced K+ induced dopamine release in the nucleus accumbens, but not the expression of locomotor sensitization in amphetamine-sensitized rats

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Kappa-type opioid receptor
60
Target ID: P41145
Gene ID: 4986.0
Gene Symbol: OPRK1
Target Organism: Homo sapiens (Human)
Agonist
2678
 3.8 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
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
Effects of the kappa-opioid receptor agonist, U69593, on the development of sensitization and on the maintenance of cocaine self-administration.
2001 Apr
Kappa opioids inhibit physiologically identified medullary pain modulating neurons and reduce morphine antinociception.
2005 Mar
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

Patents

20120322740
1
WO2012088494A1
1

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Fri Dec 15 19:37:48 UTC 2023
Edited
by admin
on Fri Dec 15 19:37:48 UTC 2023
Record UNII
J5S4K6TKTG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
U-69593
Common Name English
BENZENEACETAMIDE, N-METHYL-N-((5R,7S,8S)-7-(1-PYRROLIDINYL)-1-OXASPIRO(4.5)DEC-8-YL)-
Systematic Name English
Code System Code Type Description
FDA UNII
J5S4K6TKTG
Created by admin on Fri Dec 15 19:37:48 UTC 2023 , Edited by admin on Fri Dec 15 19:37:48 UTC 2023
PRIMARY
CAS
96744-75-1
Created by admin on Fri Dec 15 19:37:48 UTC 2023 , Edited by admin on Fri Dec 15 19:37:48 UTC 2023
PRIMARY
CHEBI
73357
Created by admin on Fri Dec 15 19:37:48 UTC 2023 , Edited by admin on Fri Dec 15 19:37:48 UTC 2023
PRIMARY
WIKIPEDIA
U 69593
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID3046326
Created by admin on Fri Dec 15 19:37:48 UTC 2023 , Edited by admin on Fri Dec 15 19:37:48 UTC 2023
PRIMARY
PUBCHEM
105104
Created by admin on Fri Dec 15 19:37:49 UTC 2023 , Edited by admin on Fri Dec 15 19:37:49 UTC 2023
PRIMARY
Related Record Type Details
Structure of U-69593 H-3
LABELED -> NON-LABELED
KAPPA-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
[35S]-GTPγS Assay Emax
EC50
Related Record Type Details
Structure of U-69593
ACTIVE MOIETY
NIH
NCATS
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