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Details

Stereochemistry RACEMIC
Molecular Formula C15H20ClN3O2
Molecular Weight 309.791
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ZACOPRIDE

SMILES

COC1=CC(N)=C(Cl)C=C1C(=O)NC2CN3CCC2CC3

InChI

InChIKey=FEROPKNOYKURCJ-UHFFFAOYSA-N
InChI=1S/C15H20ClN3O2/c1-21-14-7-12(17)11(16)6-10(14)15(20)18-13-8-19-4-2-9(13)3-5-19/h6-7,9,13H,2-5,8,17H2,1H3,(H,18,20)

HIDE SMILES / InChI

Molecular Formula C15H20ClN3O2
Molecular Weight 309.791
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Zacopride is a potent antagonist at the 5-HT3 receptor and an agonist at the 5-HT4 receptor with antiemetic, anxiolytic and nootropic effects in animal models. Zacopride also has pro-respiratory effects, both reducing sleep apnea and reversing opioid-induced respiratory depression in animal studies. Zacopride has been tested in clinical trials for the treatment of schizophrenia but was found unsuccessful.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.39 nM [Ki]
1.5 nM [Ki]
5.95 null [pEC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
0.2, 0.4, 0.8 and 1.6 mg/day for 4 weeks
Route of Administration: Oral
In Vitro Use Guide
Adrenal explants, obtained from patients undergoing expanded nephrectomy for kidney cancer, were immediately transported to the laboratory in Dulbecco Modified Eagle’s Medium (DMBM). After dissection and preincubation in DMEM at 20 C, adrenocortical fragments consisting of both glomerulosa and fasciculata zones were mixed with Bio-Gel P2 and transferred into perifusion chambers. Each perifusion column contained approximately 100 mg wet tissue: The perifusion chambers were supplied with DMEM at a constant flow rate (260 mkL/min). The pH (7.4) and temperature (37 C) were kept constant throughout the experiment. The perifusion medium was continuously gassed with a 95% O2-5% CO2 mixture. The tissues were allowed to stabilize for 2 h before zacopride was administered. Zacopride was dissolved in gassed DMEM and infused for 20 min into the perifusion chambers at the same flow rate as DMEM alone by means of a multichannel peristaltic pump. Fractions of the effluent perifusate were collected every 5 min and immediately frozen until assay. Aldosterone and cortisol concentrations were determined by RIA.
Substance Class Chemical
Record UNII
9GN3OT4156
Record Status Validated (UNII)
Record Version