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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H20ClN3O3
Molecular Weight 313.78
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORCISAPRIDE, (+)-

SMILES

CO[C@H]1CNCC[C@H]1NC(=O)C2=C(OC)C=C(N)C(Cl)=C2

InChI

InChIKey=OMLDMGPCWMBPAN-YPMHNXCESA-N
InChI=1S/C14H20ClN3O3/c1-20-12-6-10(16)9(15)5-8(12)14(19)18-11-3-4-17-7-13(11)21-2/h5-6,11,13,17H,3-4,7,16H2,1-2H3,(H,18,19)/t11-,13+/m1/s1

HIDE SMILES / InChI
Ticalopride is an isomer of the active metabolite of cisapride, which is marketed by Janssen for the treatment of nocturnal heartburn due to gastroesophageal reflux disease. Ticalopride acts through the stimulation of the serotonin 5-HT4 receptors which increases acetylcholine release in the enteric nervous system (specifically the myenteric plexus). This results in increased tone and amplitude of gastric contractions, relaxation of the pyloric sphincter and the duodenal bulb, and increased peristalsis of the duodenum and jejunum resulting in accelerated gastric emptying and intestinal transit. Phase II clinical trials of the Ticalopride are being suspended while investigators study reports of adverse events in patients with gastroesophageal reflux disease and diabetes.

Approval Year

PubMed

PubMed

TitleDatePubMed
Fast method development and rapid analysis using a screening approach for enantiomeric separations in capillary electrophoresis.
2003 Sep-Dec
Patents

Patents

Name Type Language
NORCISAPRIDE, (+)-
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-(3-METHOXY-4-PIPERIDINYL)-, CIS-(+)-
Common Name English
NARONAPRIDE METABOLITE M4
Common Name English
TICALOPRIDE
INN  
INN  
Official Name English
4-AMINO-5-CHLORO-2-METHOXY-N-((3S,4R)-3-METHOXY-4-PIPERIDINYL)BENZAMIDE
Common Name English
ticalopride [INN]
Common Name English
(+)-NORCISAPRIDE
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-((3S,4R)-3-METHOXY-4-PIPERIDINYL)-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
Code System Code Type Description
CAS
202590-69-0
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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FDA UNII
QNG273A81O
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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DRUG BANK
DB06422
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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INN
7993
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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NCI_THESAURUS
C73037
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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ChEMBL
CHEMBL2107465
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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SMS_ID
300000036923
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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PUBCHEM
216236
Created by admin on Sat Dec 16 16:47:03 GMT 2023 , Edited by admin on Sat Dec 16 16:47:03 GMT 2023
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