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
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)
| 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 | ( + / - ) |
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 |
|---|---|---|
| Cloning and expression of human 5-HT4S receptors. Effect of receptor density on their coupling to adenylyl cyclase. | 1997 Oct 20 |
|
| Cloning, expression, and pharmacology of four human 5-hydroxytryptamine 4 receptor isoforms produced by alternative splicing in the carboxyl terminus. | 1998 Jun |
|
| Anxiolytic-like effects of DAIZAC, a selective high-affinity 5-HT(3) receptor antagonist, in the mouse elevated plus-maze. | 2001 Jul-Aug |
|
| Different receptor subtypes are involved in the serotonin-induced modulation of epileptiform activity in rat frontal cortex in vitro. | 2001 Jun |
|
| Opposite effects of antidepressants and corticosterone on the sensitivity of hippocampal CA1 neurons to 5-HT1A and 5-HT4 receptor activation. | 2001 May |
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| R-zacopride, a 5-HT3 antagonist/5-HT4 agonist, reduces sleep apneas in rats. | 2001 May-Jun |
|
| Role of gas chromatography-mass spectrometry with negative ion chemical ionization in clinical and forensic toxicology, doping control, and biomonitoring. | 2002 Apr |
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| Comparison of the effects of 5-HT1A and 5-HT4 receptor activation on field potentials and epileptiform activity in rat hippocampus. | 2002 Dec |
|
| Imipramine but not 5-HT(1A) receptor agonists or neuroleptics induces adaptive changes in hippocampal 5-HT(1A) and 5-HT(4) receptors. | 2002 May 17 |
|
| Effects of serotonin-3 receptor antagonists on the intracranial self-administration of ethanol within the ventral tegmental area of Wistar rats. | 2003 Jan |
|
| Adaptive changes in the reactivity of 5-HT1A and 5-HT2 receptors induced in rat frontal cortex by repeated imipramine and citalopram. | 2003 May |
|
| Modulation of hippocampal excitability by 5-HT4 receptor agonists persists in a transgenic model of Alzheimer's disease. | 2004 |
|
| MD-354 potentiates the antinociceptive effect of clonidine in the mouse tail-flick but not hot-plate assay. | 2004 Jul 14 |
|
| Antinociception: mechanistic studies on the action of MD-354 and clonidine. Part 1. The 5-HT3 component. | 2005 Dec 28 |
|
| 5-HT(3) receptors, alcohol and aggressive behavior in mice. | 2005 May |
|
| Effect of ginseng saponins on a rat visceral hypersensitivity model. | 2005 Nov |
|
| Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats. | 2006 Feb |
|
| 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 Jul |
|
| Inhibitory effect of zacopride on Cisplatin-induced delayed emesis in ferrets. | 2006 May |
|
| 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 Sep |
|
| Modifying ligand-induced and constitutive signaling of the human 5-HT4 receptor. | 2007 Dec 19 |
|
| Effect of itopride hydrochloride on the ileal and colonic motility in guinea pig in vitro. | 2008 Jun 30 |
|
| Investigations into the binding affinities of different human 5-HT4 receptor splice variants. | 2010 |
|
| Reduced signal transduction by 5-HT4 receptors after long-term venlafaxine treatment in rats. | 2010 Oct |
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
Fri Dec 15 17:20:30 GMT 2023
by
admin
on
Fri Dec 15 17:20:30 GMT 2023
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| Record UNII |
9GN3OT4156
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C28197
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NCI_THESAURUS |
C267
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C055971
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ZACOPRIDE
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9GN3OT4156
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CHEMBL18041
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100000079385
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C152942
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SUB00127MIG
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DTXSID1048251
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5895
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108182
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90182-92-6
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ACTIVE MOIETY |
