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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyCinitapride
Identification
- Name
- Cinitapride
- Accession Number
- DB08810
- Type
- Small Molecule
- Groups
- Investigational
- Description
Cinitapride is a gastroprokinetic agent and antiulcer agent of the benzamide class which is marketed in Spain and Mexico. It acts as an agonist of the 5-HT1 and 5-HT4 receptors and as an antagonist of the 5-HT2 receptors.
- Structure
Structure for Cinitapride (DB08810)
- Synonyms
- 4-Amino-N-(1-(3-cyclohexen-1-ylmethyl)-4-piperidyl)-2-ethoxy-5-nitrobenzamide
- Cinitaprida
- Cinitapride
- Cinitapridum
- Product Ingredients
Ingredient UNII CAS InChI Key Cinitapride tartrate 2Z90GEN540 1207859-16-2 HVANMRCHFMTSEG-LREBCSMRSA-N - International/Other Brands
- Blaston / Cinmove / Cintapro / Paxapride / Pemix
- Categories
- Acids, Carbocyclic
- Agents that produce hypertension
- Alimentary Tract and Metabolism
- Amides
- Antidepressive Agents
- Benzene Derivatives
- Benzoates
- Central Nervous System Depressants
- Drugs for Functional Gastrointestinal Disorders
- Propulsives
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Serotonin 5-HT1 Receptor Agonists
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Agonists
- Serotonin Receptor Antagonists
- UNII
- R8I97I2L24
- CAS number
- 66564-14-5
- Weight
- Average: 402.4873
Monoisotopic: 402.226705468 - Chemical Formula
- C21H30N4O4
- 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
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Pharmacology
- Indication
For the treatment of gastrointestinal disorders associated with motility disturbances such as gastroesophageal reflux disease, non-ulcer dyspepsia and delayed gastric emptying.
- 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
- Toxicity
The symptoms of overdose include drowsiness, confusion and extrapyramidal effects.
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The risk or severity of adverse effects can be increased when Cinitapride is combined with (R)-warfarin. (S)-Warfarin The risk or severity of adverse effects can be increased when Cinitapride is combined with (S)-Warfarin. 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid The risk or severity of hypertension can be increased when 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid is combined with Cinitapride. 1-benzylimidazole The risk or severity of hypertension can be increased when 1-benzylimidazole is combined with Cinitapride. 4-hydroxycoumarin The risk or severity of adverse effects can be increased when Cinitapride is combined with 4-hydroxycoumarin. 4-Methoxyamphetamine The risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Cinitapride. 7-Nitroindazole The risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Cinitapride. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The metabolism of Cinitapride can be decreased when combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline. Abediterol The risk or severity of hypertension can be increased when Cinitapride is combined with Abediterol. Acebutolol Cinitapride may decrease the antihypertensive activities of Acebutolol. - Food Interactions
- Not Available
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. [PubMed:9211565]
- External Links
- Human Metabolome Database
- HMDB0015698
- KEGG Drug
- D07700
- PubChem Compound
- 68867
- PubChem Substance
- 175427098
- ChemSpider
- 62099
- ChEBI
- 135642
- ChEMBL
- CHEMBL2104523
- PharmGKB
- PA165958427
- Wikipedia
- Cinitapride
- ATC Codes
- A03FA08 — Cinitapride
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Indigestion 1
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 0.0141 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 Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- 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
- Nitrophenyl ether / Aminobenzamide / Aminobenzoic acid or derivatives / Aminophenyl ether / Benzamide / Benzoic acid or derivatives / Phenoxy compound / Nitroaromatic compound / Benzoyl / Phenol ether show 29 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
Targets
- 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. [PubMed:9211565]
- 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. [PubMed:9562338]
- 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. [PubMed:9211565]
- 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. [PubMed:9562338]
- 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. [PubMed:9211565]
- 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. [PubMed:9562338]
Drug created on January 19, 2011 16:47 / Updated on March 14, 2019 15:38