Renzapride
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Basic information
- CAS
112727-80-7- Standard SMILES
COc1cc(N)c(Cl)cc1C(=O)N[C@@H]1CCN2CCC[C@H]1C2- InChIKey
GZSKEXSLDPEFPT-IINYFYTJSA-N- Molecular formula
- C16H22ClN3O2
- Average molar mass
- 323.82 g/mol
- Monoisotopic mass
- 323.1400546
Overview
Renzapride is currently in Phase III clinical development in the United States for the treatment of constipation-predominant irritable bowel syndrome (IBS-C). It has been suggested that renzapride is effective in the treatment of irritable bowel syndrome with alternating stool pattern. It is being developed by Alizyme of the UK.
Names & identifiers
- Preferred name
- Renzapride
- IUPAC
- 4-amino-N-[(4R,5S)-1-azabicyclo[3.3.1]nonan-4-yl]-5-chloro-2-methoxybenzamide
- English name
- Renzapride
- Molecular formula
- C16H22ClN3O2
- Molecular weight
- 323.82
Names & synonyms
Renzapride112727-80-7RenzapridumRenzaprida9073C0W4E9ATL-1251BRL 24924ABRL-24924ADTXSID3013185224-Amino-5-chloro-2-methoxy-N-(1-azabicyclo-(3.3.1)-non-4-yl)benzamideBRL-24924RefChem:178863
Show more names
program AZM-112Benzamide, 4-amino-N-(1R,4S,5R)-1-azabicyclo[3.3.1]non-4-yl-5-chloro-2-methoxy-, rel-
DTXCID2017483304-amino-N-((5S,6S)-1-azabicyclo(3.3.1)nonan-6-yl)-5-chloro-2-methoxybenzamide4-amino-N-(1-azabicyclo(3.3.1)nonan-4-yl)-3-chloro-2-methoxybenzamide4-amino-N-[(4R,5S)-1-azabicyclo[3.3.1]nonan-4-yl]-5-chloro-2-methoxybenzamideRenzapride [INN](R)-RenzaprideRenzapride [INN:BAN]Renzapridum [INN-Latin]
Database identifiers
- CAS
112727-80-7- PubChem CID
- 119574
- DTXSID
DTXSID301318522- ChEMBL
CHEMBL296522- UNII
- 9073C0W4E9
- Nikkaji
- J366.656E
Properties
Computed structural propertiesFilling in
- XLogP
- 2.1
- Topological polar surface area
- 67.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 409
Physicochemical properties
- Melting point
- 260 ° · >260°
- Boiling point
- 469.2 · 469.2±45.0 °C(Predicted)
- Density
- 1.3 · 1.30±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- pka
- 13.59 · 13.59±0.20(Predicted)
- form
- Solid
- color
- White to off-white
- FDA UNII
- 9073 C0W4E9 · 9073C0W4E9
Chemistry & industry
Pharmacology
Pharmacodynamics
Renzapride is a substituted benzamide which acts on the upper gastrointestinal tract. It has been shown to enhance stomach emptying in normal subjects; doses of 2 and 5 mg decreasing by 21 and 37% respectively the volume of gastric contents aspirated 80 min after a test meal. Renzapride was found to reduce the oro-caecal transit time as assessed by the lactulose/breath hydrogen method in a dose related manner from 0.2 to 5 mg; the later dose producing a 62% reduction.
Mechanism of ActionRenzapride is a full serotonin 5-HT4 receptor agonist and partial serotonin 5-HT3 receptor antagonist.
MeSH Pharmacological ClassificationDrugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.
Applications
UsesRenzapride (BRL 24924), a substituted benzamide, is a full 5-HT4 receptor agonist with a Ki value of 115 nM. Renzapride (BRL 24924) is also a 5HT2b and 5HT3 receptor antagonist[1]. Renzapride could be used for constipation predominant irritable bowel syndrome (C-IBS) study[2].
Related reactions
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Compound notes
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