U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C14H20ClN3O3
Molecular Weight 313.7804
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORCISAPRIDE

SMILES

COc1cc(c(cc1C(=N[C@]2([H])CCNC[C@]2([H])OC)O)Cl)N

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

Molecular Formula C14H20ClN3O3
Molecular Weight 313.7804
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Substance Class Chemical
Created
by admin
on Sat Jun 26 06:33:45 UTC 2021
Edited
by admin
on Sat Jun 26 06:33:45 UTC 2021
Record UNII
U221XI117N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORCISAPRIDE
Common Name English
(+/-)-NORCISAPRIDE
Common Name English
BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-((3R,4S)-3-METHOXY-4-PIPERIDINYL)-, REL-
Systematic Name English
BENZAMIDE, 4-AMINO-5-CHLORO-2-METHOXY-N-(3-METHOXY-4-PIPERIDINYL)-, CIS-
Common Name English
CIS-4-AMINO-5-CHLORO-2-METHOXY-N-(3-METHOXY-PIPERIDIN-4-YL)-BENZAMIDE
Common Name English
Code System Code Type Description
CAS
83863-69-8
Created by admin on Sat Jun 26 06:33:45 UTC 2021 , Edited by admin on Sat Jun 26 06:33:45 UTC 2021
PRIMARY
FDA UNII
U221XI117N
Created by admin on Sat Jun 26 06:33:45 UTC 2021 , Edited by admin on Sat Jun 26 06:33:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
281-134-9
Created by admin on Sat Jun 26 06:33:45 UTC 2021 , Edited by admin on Sat Jun 26 06:33:45 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> AGONIST
ENANTIOMER -> RACEMATE
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY