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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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.7 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
39K8JHE8XN
Record Status Validated (UNII)
Record Version