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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

Description
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

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
The 5-HT4 receptor: molecular cloning and pharmacological characterization of two splice variants.
1995 Jun 15
Serotoninergic modulation of excitability in area CA1 of the in vitro rat hippocampus.
1995 Oct 27
Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor.
1996 Nov 25
Different receptor subtypes are involved in the serotonin-induced modulation of epileptiform activity in rat frontal cortex in vitro.
2001 Jun
R-zacopride, a 5-HT3 antagonist/5-HT4 agonist, reduces sleep apneas in rats.
2001 May-Jun
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
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
Dose-effect study of Gelsemium sempervirens in high dilutions on anxiety-related responses in mice.
2010 Jul
Reduced signal transduction by 5-HT4 receptors after long-term venlafaxine treatment in rats.
2010 Oct
Patents

Sample Use Guides

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.
Name Type Language
ZACOPRIDE
INN  
INN  
Official Name English
(±)-ZACOPRIDE
Common Name English
4-AMINO-5-CHLORO-N-3-QUINUCLIDINYL-O-ANISAMIDE
Common Name English
BENZAMIDE, 4-AMINO-N-1-AZABICYCLO(2.2.2)OCT-3-YL-5-CHLORO-2-METHOXY-
Systematic Name English
zacopride [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
NCI_THESAURUS C267
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
Code System Code Type Description
MESH
C055971
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
WIKIPEDIA
ZACOPRIDE
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
FDA UNII
9GN3OT4156
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL18041
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
SMS_ID
100000079385
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
NCI_THESAURUS
C152942
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
EVMPD
SUB00127MIG
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID1048251
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
INN
5895
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
PUBCHEM
108182
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY
CAS
90182-92-6
Created by admin on Fri Dec 15 17:20:30 GMT 2023 , Edited by admin on Fri Dec 15 17:20:30 GMT 2023
PRIMARY