Identification
- Summary
Cinitapride is a benzamide with gastroprokinetic and antiemetic properties typically used for the treatment of gastrointestinal motility disorders such as gastroesophageal reflux disease (GERD), non-ulcer dyspepsia, and delayed gastric emptying.
- Generic Name
- Cinitapride
- DrugBank Accession Number
- DB08810
- Background
Cinitapride is a gastroprokinetic agent and antiulcer benzamide with agonist activity at 5-HT1 and 5-HT4 receptors and antagonist activity at 5-HT2 receptors. It is marketed in Spain and Mexico.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Cinitapride (DB08810)
- Weight
- Average: 402.4873
Monoisotopic: 402.226705468 - Chemical Formula
- C21H30N4O4
- Synonyms
- 4-Amino-N-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide
- Cinitaprida
- Cinitapride
- Cinitapridum
Pharmacology
- Indication
It is indicated to treat gastrointestinal disorders associated with motility disturbances like gastroesophageal reflux disease (GERD), non-ulcer dyspepsia and delayed gastric emptying.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to manage Dyspepsia Combination Product in combination with: Simethicone (DB09512) •••••••••••• ••••• ••••••••••• ••••••• ••••••• •••••••• Used in combination to manage Flatulence Combination Product in combination with: Simethicone (DB09512) •••••••••••• ••••• ••••••••••• ••••••• ••••••• •••••••• Used as adjunct in combination to manage Gastro-esophageal reflux disease (gerd) Combination Product in combination with: Simethicone (DB09512) •••••••••••• ••••• ••••••••••• •••••• •••• ••••••••• ••••••••• ••••••••••• ••••••• ••••••• •••••••• Management of Gastroesophageal reflux •••••••••••• ••••••••••• •••••• •••• ••••••••• ••••••••• •••••••• Management of Decreased gastrointestinal motility ••• ••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Cinitapride is a substituted benzamide with 5-HT receptor antagonist and agonist activity.
Target Actions Organism A5-hydroxytryptamine receptor 1A agonistHumans A5-hydroxytryptamine receptor 2A antagonistHumans U5-hydroxytryptamine receptor 4 agonistHumans - Absorption
The absorption of cinitapride (12mg) following oral administration was rapid, with peak levels being achieved 2 h after dosing; absorption following intramuscular administration (4mg) was even more rapid, with peak levels (50% more that oral levels) being achieved 1 h after dosing.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
3-5 h during the first 8 h and a residual half-life greater than 15 h thereafter.
- 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
The symptoms of overdose include drowsiness, confusion and extrapyramidal effects.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Cinitapride is combined with 1,2-Benzodiazepine. Acebutolol Cinitapride may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with Cinitapride. Acemetacin The risk or severity of hypertension can be increased when Cinitapride is combined with Acemetacin. Acenocoumarol The risk or severity of adverse effects can be increased when Cinitapride is combined with Acenocoumarol. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cinitapride tartrate 2Z90GEN540 1207859-16-2 HVANMRCHFMTSEG-LREBCSMRSA-N - International/Other Brands
- Blaston / Cinmove / Cintapro / Paxapride / Pemix
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ROGASTRIL PLUS ® SUSPENSIÓN Cinitapride tartrate (10 mg) + Simethicone (2000 mg) Suspension Oral LABORATORIOS SIEGFRIED S.A.S. 2017-08-17 Not applicable Colombia 
ROGASTRIL PLUS® Cinitapride tartrate (1 mg) + Simethicone (200 mg) Tablet Oral LABORATORIOS SIEGFRIED S.A.S. 2017-04-25 Not applicable Colombia ROGASTRIL® PLUS TABLETAS MASTICABLES Cinitapride tartrate (1 mg) + Simethicone (200 mg) Tablet, chewable Oral LABORATORIOS SIEGFRIED S.A.S. 2017-11-15 Not applicable Colombia
Categories
- ATC Codes
- A03FA08 — Cinitapride
- Drug Categories
- Acids, Carbocyclic
- Agents that produce hypertension
- Alimentary Tract and Metabolism
- Amides
- Anti-Ulcer Agents
- Antidepressive Agents
- Benzene Derivatives
- Benzoates
- Central Nervous System Depressants
- Drugs for Functional Gastrointestinal Disorders
- Gastrointestinal Agents
- Propulsives
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Agonists
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Agonists
- Serotonin Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Nitrobenzenes
- Direct Parent
- Nitrophenyl ethers
- Alternative Parents
- Aminobenzamides / Aminophenyl ethers / Benzamides / Phenoxy compounds / Aniline and substituted anilines / Nitroaromatic compounds / Benzoyl derivatives / Alkyl aryl ethers / Piperidines / Trialkylamines show 10 more
- Substituents
- Alkyl aryl ether / Allyl-type 1,3-dipolar organic compound / Amine / Amino acid or derivatives / Aminobenzamide / Aminobenzoic acid or derivatives / Aminophenyl ether / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle show 29 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- R8I97I2L24
- CAS number
- 66564-14-5
- InChI Key
- ZDLBNXXKDMLZMF-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H30N4O4/c1-2-29-20-13-18(22)19(25(27)28)12-17(20)21(26)23-16-8-10-24(11-9-16)14-15-6-4-3-5-7-15/h3-4,12-13,15-16H,2,5-11,14,22H2,1H3,(H,23,26)
- IUPAC Name
- 4-amino-N-{1-[(cyclohex-3-en-1-yl)methyl]piperidin-4-yl}-2-ethoxy-5-nitrobenzamide
- SMILES
- CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O
References
- General References
- Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [Article]
- External Links
- Human Metabolome Database
- HMDB0015698
- KEGG Drug
- D07700
- PubChem Compound
- 68867
- PubChem Substance
- 175427098
- ChemSpider
- 62099
- 21125
- ChEBI
- 135642
- ChEMBL
- CHEMBL2104523
- PharmGKB
- PA165958427
- Wikipedia
- Cinitapride
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 1.00 mg Solution Oral 20.000 mg Granule Oral 1.0 mg Tablet Oral 1.0 mg Tablet Oral 1 mg Granule Oral 1.00 mg Tablet Oral 1.000 mg Suspension Oral Tablet Oral Solution Oral 20 mg Solution Oral 2000000 mg Tablet, chewable Oral Tablet Oral 1.373 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0141 mg/mL ALOGPS logP 3.7 ALOGPS logP 2.79 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 13.62 Chemaxon pKa (Strongest Basic) 9.74 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 110.73 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 114.58 m3·mol-1 Chemaxon Polarizability 44.37 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 Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9916 Blood Brain Barrier + 0.9314 Caco-2 permeable - 0.5973 P-glycoprotein substrate Substrate 0.8692 P-glycoprotein inhibitor I Inhibitor 0.5895 P-glycoprotein inhibitor II Non-inhibitor 0.8347 Renal organic cation transporter Non-inhibitor 0.7496 CYP450 2C9 substrate Non-substrate 0.8928 CYP450 2D6 substrate Non-substrate 0.8126 CYP450 3A4 substrate Substrate 0.5721 CYP450 1A2 substrate Non-inhibitor 0.6663 CYP450 2C9 inhibitor Non-inhibitor 0.7521 CYP450 2D6 inhibitor Non-inhibitor 0.7862 CYP450 2C19 inhibitor Inhibitor 0.5746 CYP450 3A4 inhibitor Non-inhibitor 0.5286 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5396 Ames test AMES toxic 0.6766 Carcinogenicity Non-carcinogens 0.7628 Biodegradation Not ready biodegradable 0.8614 Rat acute toxicity 2.6773 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5217 hERG inhibition (predictor II) Inhibitor 0.6969
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-009x-8579000000-39b68a617611dab9e95b 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]- 210.3751447 predictedDarkChem Lite v0.1.0 [M-H]- 190.34123 predictedDeepCCS 1.0 (2019) [M+H]+ 210.6773447 predictedDarkChem Lite v0.1.0 [M+H]+ 192.69923 predictedDeepCCS 1.0 (2019) [M+Na]+ 210.2891447 predictedDarkChem Lite v0.1.0 [M+Na]+ 198.79237 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [Article]
- Alarcon de la Lastra C, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [Article]
- Alarcon de la Lastra C, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- Serotonin receptor activity
- Specific 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 ...
- Gene Name
- HTR4
- Uniprot ID
- Q13639
- Uniprot Name
- 5-hydroxytryptamine receptor 4
- Molecular Weight
- 43760.975 Da
References
- Alarcon-de-la-Lastra Romero C, Lopez A, Martin MJ, la Casa C, Motilva V: Cinitapride protects against ethanol-induced gastric mucosal injury in rats: role of 5-hydroxytryptamine, prostaglandins and sulfhydryl compounds. Pharmacology. 1997 Apr;54(4):193-202. [Article]
- Alarcon de la Lastra C, La Casa C, Martin MJ, Motilva V: Effects of cinitapride on gastric ulceration and secretion in rats. Inflamm Res. 1998 Mar;47(3):131-6. [Article]
Drug created at January 19, 2011 23:47 / Updated at June 16, 2021 12:31