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)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20950056Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20950056
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1899 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24365159 |
0.39 nM [Ki] | ||
Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1312602 |
1.5 nM [Ki] | ||
Target ID: CHEMBL1875 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12540230 |
5.95 null [pEC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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The 5-HT4 receptor: molecular cloning and pharmacological characterization of two splice variants. | 1995 Jun 15 |
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Serotoninergic modulation of excitability in area CA1 of the in vitro rat hippocampus. | 1995 Oct 27 |
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Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor. | 1996 Nov 25 |
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Different receptor subtypes are involved in the serotonin-induced modulation of epileptiform activity in rat frontal cortex in vitro. | 2001 Jun |
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R-zacopride, a 5-HT3 antagonist/5-HT4 agonist, reduces sleep apneas in rats. | 2001 May-Jun |
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Modulation of hippocampal excitability by 5-HT4 receptor agonists persists in a transgenic model of Alzheimer's disease. | 2004 |
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MD-354 potentiates the antinociceptive effect of clonidine in the mouse tail-flick but not hot-plate assay. | 2004 Jul 14 |
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Effect of ginseng saponins on a rat visceral hypersensitivity model. | 2005 Nov |
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Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats. | 2006 Feb |
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Dose-effect study of Gelsemium sempervirens in high dilutions on anxiety-related responses in mice. | 2010 Jul |
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Reduced signal transduction by 5-HT4 receptors after long-term venlafaxine treatment in rats. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1514881
0.2, 0.4, 0.8 and 1.6 mg/day for 4 weeks
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8263156
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.
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Classification Tree | Code System | Code | ||
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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
SALT/SOLVATE (PARENT)