RENZAPRIDE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H22ClN3O2.ClH
Molecular Weight	360.279
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.COC1=CC(N)=C(Cl)C=C1C(=O)N[C@@H]2CC[N@@]3CCC[C@H]2C3

InChI

InChIKey=WYONTPMGUQWRKN-WUCQATPYSA-N

InChI=1S/C16H22ClN3O2.ClH/c1-22-15-8-13(18)12(17)7-11(15)16(21)19-14-4-6-20-5-2-3-10(14)9-20;/h7-8,10,14H,2-6,9,18H2,1H3,(H,19,21);1H/t10?,14-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C16H22ClN3O2
Molecular Weight	323.818
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18922103 | https://www.ncbi.nlm.nih.gov/pubmed/18284648 | https://clinicaltrials.gov/ct2/show/NCT00268879 | https://clinicaltrials.gov/ct2/show/NCT00607971 | https://www.ncbi.nlm.nih.gov/pubmed/18034998

Renzapride (BRL-24924) is a mixed 5-hydroxytryptamine type 4 (5-HT4) agonist and 5-HT3 receptor antagonist. This compound has a stimulatory effect on gastrointestinal motility and transit. Renzapride has been evaluated for use in treatment of irritable bowel syndrome (IBS). Data also suggested a potentially beneficial effect on abdominal pain/discomfort in women with constipation-predominant irritable bowel syndrome. Phase III clinical trials investigated if this drug could help alleviate the symptoms associated with this type of IBS. However, one phase III study has been terminated due to inefficient efficacy (compared to placebo).

Approval Year

PubMed

Title	Date	PubMed
The 5-HT4 receptor: molecular cloning and pharmacological characterization of two splice variants.	1995 Jun 15	7796807
[3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor.	1996 May 23	8813606
Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor.	1996 Nov 25	8946946
[3H]RS 57639, a high affinity, selective 5-HT4 receptor partial agonist, specifically labels guinea-pig striatal and rat cloned (5-HT4S and 5-HT4L) receptors.	1997 Apr-May	9225293
Cloning and expression of human 5-HT4S receptors. Effect of receptor density on their coupling to adenylyl cyclase.	1997 Oct 20	9351641
Cloning, expression, and pharmacology of four human 5-hydroxytryptamine 4 receptor isoforms produced by alternative splicing in the carboxyl terminus.	1998 Jun	9603189
Isolation of the serotoninergic 5-HT4(e) receptor from human heart and comparative analysis of its pharmacological profile in C6-glial and CHO cell lines.	2000 Feb	10683202
Pharmacological characterization of the human 5-HT(4(d)) receptor splice variant stably expressed in Chinese hamster ovary cells.	2000 Oct	11030734
5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle.	2001 Feb	11218067

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:30:57 GMT 2023` Edited by `admin` on `Sat Dec 16 05:30:57 GMT 2023`
Record UNII	6H0SNK4GNT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RENZAPRIDE HYDROCHLORIDE

Common Name

English

BENZAMIDE, 4-AMINO-N-(1R,4S,5R)-1-AZABICYCLO(3.3.1)NON-4-YL-5-CHLORO-2-METHOXY-, HYDROCHLORIDE (1:1), REL-

Common Name

English

BENZAMIDE, 4-AMINO-N-1-AZABICYCLO(3.3.1)NON-4-YL-5-CHLORO-2-METHOXY-, MONOHYDROCHLORIDE, ENDO-(±)-

Common Name

English

BRL-24924

Code

English

Code System Code Type Description

SMS_ID

300000001440