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
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
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
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C257
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202590-69-0
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7993
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C73037
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CHEMBL2107465
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300000036923
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216236
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ACTIVE MOIETY
PARENT (METABOLITE)