Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Renzapride
- DrugBank Accession Number
- DB04917
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Renzapride (DB04917)
- Weight
- Average: 323.818
Monoisotopic: 323.14005467 - Chemical Formula
- C16H22ClN3O2
- Synonyms
- Renzapride
Pharmacology
- Indication
For the treatment of constipation-predominant irritable bowel syndrome (IBS-C).
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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 action
Renzapride is a full serotonin 5-HT4 receptor agonist and partial serotonin 5-HT3 receptor antagonist.
Target Actions Organism A5-hydroxytryptamine receptor 4 modulatorHumans U5-hydroxytryptamine receptor 3A Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Renzapride is combined with 1,2-Benzodiazepine. Acenocoumarol The risk or severity of adverse effects can be increased when Renzapride is combined with Acenocoumarol. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Renzapride. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Renzapride. Agomelatine The risk or severity of CNS depression can be increased when Renzapride is combined with Agomelatine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Aminobenzamides
- Alternative Parents
- 3-halobenzoic acids and derivatives / Aminophenyl ethers / Methoxyanilines / Benzamides / Phenoxy compounds / Methoxybenzenes / Anisoles / Benzoyl derivatives / Alkyl aryl ethers / Chlorobenzenes show 11 more
- Substituents
- 3-halobenzoic acid or derivatives / Alkyl aryl ether / Amine / Amino acid or derivatives / Aminobenzamide / Aminophenyl ether / Aniline or substituted anilines / Anisole / Aromatic heteropolycyclic compound / Aryl chloride show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 9073C0W4E9
- CAS number
- 112727-80-7
- InChI Key
- YFUAYKVMQVBSNG-UHFFFAOYSA-N
- InChI
- InChI=1S/C16H22ClN3O2/c1-22-15-11(4-5-12(18)14(15)17)16(21)19-13-6-8-20-7-2-3-10(13)9-20/h4-5,10,13H,2-3,6-9,18H2,1H3,(H,19,21)
- IUPAC Name
- 4-amino-N-{1-azabicyclo[3.3.1]nonan-4-yl}-3-chloro-2-methoxybenzamide
- SMILES
- COC1=C(C=CC(N)=C1Cl)C(=O)NC1CCN2CCCC1C2
References
- General References
- Staniforth DH, Pennick M: Human pharmacology of renzapride: a new gastrokinetic benzamide without dopamine antagonist properties. Eur J Clin Pharmacol. 1990;38(2):161-4. [Article]
- Mackie AD, Ferrington C, Cowan S, Merrick MV, Baird JD, Palmer KR: The effects of renzapride, a novel prokinetic agent, in diabetic gastroparesis. Aliment Pharmacol Ther. 1991 Apr;5(2):135-42. [Article]
- Craig DA, Clarke DE: Peristalsis evoked by 5-HT and renzapride: evidence for putative 5-HT4 receptor activation. Br J Pharmacol. 1991 Mar;102(3):563-4. [Article]
- Tack J, Middleton SJ, Horne MC, Piessevaux H, Bloor JS, Meyers NL, Palmer RM: Pilot study of the efficacy of renzapride on gastrointestinal motility and symptoms in patients with constipation-predominant irritable bowel syndrome. Aliment Pharmacol Ther. 2006 Jun 1;23(11):1655-65. [Article]
- External Links
- PubChem Compound
- 3052778
- PubChem Substance
- 175426902
- ChemSpider
- 2314555
- Wikipedia
- Renzapride
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Completed Treatment Irritable Bowel Syndrome (IBS) 1 somestatus stop reason just information to hide 3 Terminated Not Available Irritable Bowel Syndrome With Constipation (IBS-C) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.195 mg/mL ALOGPS logP 2.29 ALOGPS logP 1.14 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 14.68 Chemaxon pKa (Strongest Basic) 8.8 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 67.59 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 88.74 m3·mol-1 Chemaxon Polarizability 33.47 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.994 Blood Brain Barrier + 0.9483 Caco-2 permeable + 0.5727 P-glycoprotein substrate Substrate 0.7809 P-glycoprotein inhibitor I Non-inhibitor 0.5268 P-glycoprotein inhibitor II Non-inhibitor 0.7462 Renal organic cation transporter Inhibitor 0.5414 CYP450 2C9 substrate Non-substrate 0.8584 CYP450 2D6 substrate Substrate 0.5485 CYP450 3A4 substrate Substrate 0.7339 CYP450 1A2 substrate Non-inhibitor 0.5744 CYP450 2C9 inhibitor Non-inhibitor 0.5085 CYP450 2D6 inhibitor Inhibitor 0.6059 CYP450 2C19 inhibitor Inhibitor 0.7174 CYP450 3A4 inhibitor Inhibitor 0.5694 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6351 Ames test AMES toxic 0.6043 Carcinogenicity Non-carcinogens 0.9105 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.5563 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8478 hERG inhibition (predictor II) Inhibitor 0.8497
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0009000000-55e7aa40f91ab1556bbc Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0fk9-0019000000-43c5fafee1a848f0c663 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0209000000-2927fce295aa4fd08104 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-3195000000-500ec1335d304c5027ab Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0791000000-f2474157880c8c23a65d Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001r-9853000000-a7416a6babc450c27a17 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 169.00438 predictedDeepCCS 1.0 (2019) [M+H]+ 171.36237 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.45552 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Modulator
- General Function
- This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that stimulate adenylate cyclase
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HTR4
- Uniprot ID
- Q13639
- Uniprot Name
- 5-hydroxytryptamine receptor 4
- Molecular Weight
- 43760.975 Da
References
- Craig DA, Clarke DE: Peristalsis evoked by 5-HT and renzapride: evidence for putative 5-HT4 receptor activation. Br J Pharmacol. 1991 Mar;102(3):563-4. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Forms serotonin (5-hydroxytryptamine/5-HT3)-activated cation-selective channel complexes, which when activated cause fast, depolarizing responses in neurons
- Specific Function
- Excitatory extracellular ligand-gated monoatomic ion channel activity
- Gene Name
- HTR3A
- Uniprot ID
- P46098
- Uniprot Name
- 5-hydroxytryptamine receptor 3A
- Molecular Weight
- 55279.835 Da
References
- Tack J, Middleton SJ, Horne MC, Piessevaux H, Bloor JS, Meyers NL, Palmer RM: Pilot study of the efficacy of renzapride on gastrointestinal motility and symptoms in patients with constipation-predominant irritable bowel syndrome. Aliment Pharmacol Ther. 2006 Jun 1;23(11):1655-65. [Article]
Drug created at October 21, 2007 22:23 / Updated at August 26, 2024 19:23