Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C15H20ClN3O2.ClH |
| Molecular Weight | 346.252 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=C(C=C(Cl)C(N)=C1)C(=O)NC2CN3CCC2CC3
InChI
InChIKey=ITXVOUSORXSTQH-UHFFFAOYSA-N
InChI=1S/C15H20ClN3O2.ClH/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);1H
| Molecular Formula | C15H20ClN3O2 |
| Molecular Weight | 309.791 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1514881 | https://www.ncbi.nlm.nih.gov/pubmed/12540230 | https://www.ncbi.nlm.nih.gov/pubmed/24365159 | https://www.ncbi.nlm.nih.gov/pubmed/1312602 | https://www.ncbi.nlm.nih.gov/pubmed/8263156
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1514881 | https://www.ncbi.nlm.nih.gov/pubmed/12540230 | https://www.ncbi.nlm.nih.gov/pubmed/24365159 | https://www.ncbi.nlm.nih.gov/pubmed/1312602 | https://www.ncbi.nlm.nih.gov/pubmed/8263156
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.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Reduced signal transduction by 5-HT4 receptors after long-term venlafaxine treatment in rats. | 2010-10 |
|
| Dose-effect study of Gelsemium sempervirens in high dilutions on anxiety-related responses in mice. | 2010-07 |
|
| Investigations into the binding affinities of different human 5-HT4 receptor splice variants. | 2010 |
|
| Long-term treatment with fluoxetine induces desensitization of 5-HT4 receptor-dependent signalling and functionality in rat brain. | 2009-08 |
|
| 5-Hydroxytryptamine Receptor Subtypes and their Modulators with Therapeutic Potentials. | 2009-06 |
|
| 5-HT inhibition of rat insulin 2 promoter Cre recombinase transgene and proopiomelanocortin neuron excitability in the mouse arcuate nucleus. | 2009-03-03 |
|
| Engineered G-protein Coupled Receptors are Powerful Tools to Investigate Biological Processes and Behaviors. | 2009 |
|
| Effect of itopride hydrochloride on the ileal and colonic motility in guinea pig in vitro. | 2008-06-30 |
|
| Modifying ligand-induced and constitutive signaling of the human 5-HT4 receptor. | 2007-12-19 |
|
| Imipramine and citalopram reverse corticosterone-induced alterations in the effects of the activation of 5-HT(1A) and 5-HT(2) receptors in rat frontal cortex. | 2006-09 |
|
| Imipramine treatment ameliorates corticosterone-induced alterations in the effects of 5-HT1A and 5-HT4 receptor activation in the CA1 area of rat hippocampus. | 2006-07 |
|
| Inhibitory effect of zacopride on Cisplatin-induced delayed emesis in ferrets. | 2006-05 |
|
| Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats. | 2006-02 |
|
| Antinociception: mechanistic studies on the action of MD-354 and clonidine. Part 1. The 5-HT3 component. | 2005-12-28 |
|
| Effect of ginseng saponins on a rat visceral hypersensitivity model. | 2005-11 |
|
| 5-HT(3) receptors, alcohol and aggressive behavior in mice. | 2005-05 |
|
| MD-354 potentiates the antinociceptive effect of clonidine in the mouse tail-flick but not hot-plate assay. | 2004-07-14 |
|
| Modulation of hippocampal excitability by 5-HT4 receptor agonists persists in a transgenic model of Alzheimer's disease. | 2004 |
|
| Adaptive changes in the reactivity of 5-HT1A and 5-HT2 receptors induced in rat frontal cortex by repeated imipramine and citalopram. | 2003-05 |
|
| Effects of serotonin-3 receptor antagonists on the intracranial self-administration of ethanol within the ventral tegmental area of Wistar rats. | 2003-01 |
|
| Comparison of the effects of 5-HT1A and 5-HT4 receptor activation on field potentials and epileptiform activity in rat hippocampus. | 2002-12 |
|
| Imipramine but not 5-HT(1A) receptor agonists or neuroleptics induces adaptive changes in hippocampal 5-HT(1A) and 5-HT(4) receptors. | 2002-05-17 |
|
| Role of gas chromatography-mass spectrometry with negative ion chemical ionization in clinical and forensic toxicology, doping control, and biomonitoring. | 2002-04 |
|
| Anxiolytic-like effects of DAIZAC, a selective high-affinity 5-HT(3) receptor antagonist, in the mouse elevated plus-maze. | 2001-08-18 |
|
| R-zacopride, a 5-HT3 antagonist/5-HT4 agonist, reduces sleep apneas in rats. | 2001-06-23 |
|
| Different receptor subtypes are involved in the serotonin-induced modulation of epileptiform activity in rat frontal cortex in vitro. | 2001-06 |
|
| Opposite effects of antidepressants and corticosterone on the sensitivity of hippocampal CA1 neurons to 5-HT1A and 5-HT4 receptor activation. | 2001-05 |
|
| Cloning, expression, and pharmacology of four human 5-hydroxytryptamine 4 receptor isoforms produced by alternative splicing in the carboxyl terminus. | 1998-06 |
|
| Cloning and expression of human 5-HT4S receptors. Effect of receptor density on their coupling to adenylyl cyclase. | 1997-10-20 |
|
| [3H]RS 57639, a high affinity, selective 5-HT4 receptor partial agonist, specifically labels guinea-pig striatal and rat cloned (5-HT4S and 5-HT4L) receptors. | 1997-04-01 |
|
| Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor. | 1996-11-25 |
|
| [3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor. | 1996-05-23 |
|
| Serotoninergic modulation of excitability in area CA1 of the in vitro rat hippocampus. | 1995-10-27 |
|
| The 5-HT4 receptor: molecular cloning and pharmacological characterization of two splice variants. | 1995-06-15 |
Patents
Sample Use Guides
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
Created
by
admin
on
Edited
Mon Mar 31 21:23:02 GMT 2025
by
admin
on
Mon Mar 31 21:23:02 GMT 2025
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| Record UNII |
BJ3775635U
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| Record Status |
Validated (UNII)
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| Record Version |
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |
