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Details

Stereochemistry RACEMIC
Molecular Formula C19H26Cl2N2O
Molecular Weight 369.329
Optical Activity ( + / - )
Defined Stereocenters 1 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of U-50488

SMILES

CN([C@H]1CCCC[C@H]1N2CCCC2)C(=O)CC3=CC=C(Cl)C(Cl)=C3

InChI

InChIKey=VQLPLYSROCPWFF-QRWMCTBCSA-N
InChI=1S/C19H26Cl2N2O/c1-22(19(24)13-14-8-9-15(20)16(21)12-14)17-6-2-3-7-18(17)23-10-4-5-11-23/h8-9,12,17-18H,2-7,10-11,13H2,1H3/t17?,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H26Cl2N2O
Molecular Weight 369.329
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://google.com/patents/DE2749950C2 | https://www.ncbi.nlm.nih.gov/pubmed/28116477 | https://www.ncbi.nlm.nih.gov/pubmed/26330078 | https://www.ncbi.nlm.nih.gov/pubmed/26303466

U-50488 is a drug which acts as a highly selective κ-opioid agonist, but without any μ-opioid antagonist effects. U-50488 has analgesic, diuretic and antitussive effects, and reverses the memory impairment produced by anticholinergic drugs.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.7 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Regulation and function of MeCP2 Ser421 phosphorylation in U50488-induced conditioned place aversion in mice.
2017 Mar
Patents

Patents

Sample Use Guides

C57BL6 male mice were placed in the open field for 30 min prior to injection of vehicle (saline) or 5 mg/kg i.p. U50488 (Tocris). Two hours later, mice were transcardially perfused with 4% paraformaldehyde (PFA) and 0.1 M PBS. Brains were postfixed overnight in PBS with 4% PFA and then transferred to 20% sucrose in PBS with 4% PFA.
Route of Administration: Intraperitoneal
Flasks of T. brucei were seeded at 1 x 104 cells/ml and incubated in the presence of the U50,488 for 3 days. Flasks were set up in triplicate for each inhibitor at multiples of EC50 along with 3 control flasks with no inhibitor added. Pentamidine and U50,488 were added in DMSO in a volume of 0.1% of the culture. Eflornithine was dissolved directly in HMI9-T medium and sterilised by 0.22 mMfiltration before diluting into the cell culture.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:11:06 GMT 2023
Edited
by admin
on Fri Dec 15 18:11:06 GMT 2023
Record UNII
39K8JHE8XN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
U-50488
Code English
BENZENEACETAMIDE, 3,4-DICHLORO-N-METHYL-N-(2-(1-PYRROLIDINYL)CYCLOHEXYL)-, TRANS-
Common Name English
(±)-TRANS-U 50488
Common Name English
3,4-DICHLORO-N-METHYL-N-(2-(1-PYRROLIDINYL)-CYCLOHEXYL)-BENZENEACETAMIDE, (TRANS)-ISOMER
Common Name English
Code System Code Type Description
FDA UNII
39K8JHE8XN
Created by admin on Fri Dec 15 18:11:06 GMT 2023 , Edited by admin on Fri Dec 15 18:11:06 GMT 2023
PRIMARY
CAS
67198-13-4
Created by admin on Fri Dec 15 18:11:06 GMT 2023 , Edited by admin on Fri Dec 15 18:11:06 GMT 2023
PRIMARY
CHEBI
73358
Created by admin on Fri Dec 15 18:11:06 GMT 2023 , Edited by admin on Fri Dec 15 18:11:06 GMT 2023
PRIMARY
PUBCHEM
68616
Created by admin on Fri Dec 15 18:11:06 GMT 2023 , Edited by admin on Fri Dec 15 18:11:06 GMT 2023
PRIMARY
WIKIPEDIA
U-50488
Created by admin on Fri Dec 15 18:11:06 GMT 2023 , Edited by admin on Fri Dec 15 18:11:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID50849401
Created by admin on Fri Dec 15 18:11:06 GMT 2023 , Edited by admin on Fri Dec 15 18:11:06 GMT 2023
PRIMARY
Related Record Type Details
TARGET->LIGAND
BINDING
IC50
TARGET->LIGAND
WEAK BINDER
BINDING
IC50
TARGET -> AGONIST
Selective for the kappa receptor no mu activity.
BINDING
IC50
Related Record Type Details
ACTIVE MOIETY