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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

Molecular Formula C14H20ClN3O3
Molecular Weight 313.78
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
Patents

Patents

Substance Class Chemical
Created
by admin
on Thu Jul 06 22:14:07 UTC 2023
Edited
by admin
on Thu Jul 06 22:14:07 UTC 2023
Record UNII
QNG273A81O
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
Code System Code Type Description
CAS
202590-69-0
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
FDA UNII
QNG273A81O
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
DRUG BANK
DB06422
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
INN
7993
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
NCI_THESAURUS
C73037
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107465
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
SMS_ID
300000036923
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
PUBCHEM
216236
Created by admin on Thu Jul 06 22:14:08 UTC 2023 , Edited by admin on Thu Jul 06 22:14:08 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER
TARGET -> AGONIST
Related Record Type Details
PARENT -> METABOLITE
FECAL; PLASMA; URINE
Related Record Type Details
ACTIVE MOIETY