Cinitapride

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
Thumb
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.

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Cinitapride is a substituted benzamide with 5-HT receptor antagonist and agonist activity.

TargetActionsOrganism
A5-hydroxytryptamine receptor 1A
agonist
Humans
A5-hydroxytryptamine receptor 2A
antagonist
Humans
U5-hydroxytryptamine receptor 4
agonist
Humans
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
Adverseeffects
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Toxicity

The symptoms of overdose include drowsiness, confusion and extrapyramidal effects.

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Cinitapride is combined with 1,2-Benzodiazepine.
AcebutololCinitapride may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with Cinitapride.
AcemetacinThe risk or severity of hypertension can be increased when Cinitapride is combined with Acemetacin.
AcenocoumarolThe risk or severity of adverse effects can be increased when Cinitapride is combined with Acenocoumarol.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Cinitapride.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Cinitapride.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Cinitapride.
AclidiniumCinitapride may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Agomelatine is combined with Cinitapride.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cinitapride tartrate2Z90GEN5401207859-16-2HVANMRCHFMTSEG-LREBCSMRSA-N
International/Other Brands
Blaston / Cinmove / Cintapro / Paxapride / Pemix
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ROGASTRIL PLUS ® SUSPENSIÓNCinitapride tartrate (10 mg) + Simethicone (2000 mg)SuspensionOralLABORATORIOS SIEGFRIED S.A.S.2017-08-17Not applicableColombia flag
ROGASTRIL PLUS®Cinitapride tartrate (1 mg) + Simethicone (200 mg)TabletOralLABORATORIOS SIEGFRIED S.A.S.2017-04-25Not applicableColombia flag
ROGASTRIL® PLUS TABLETAS MASTICABLESCinitapride tartrate (1 mg) + Simethicone (200 mg)Tablet, chewableOralLABORATORIOS SIEGFRIED S.A.S.2017-11-15Not applicableColombia flag

Categories

ATC Codes
A03FA08 — Cinitapride
Drug Categories
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
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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
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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
  1. 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]
Human Metabolome Database
HMDB0015698
KEGG Drug
D07700
PubChem Compound
68867
PubChem Substance
175427098
ChemSpider
62099
RxNav
21125
ChEBI
135642
ChEMBL
CHEMBL2104523
PharmGKB
PA165958427
Wikipedia
Cinitapride

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentDyspepsia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral1 mg
SuspensionOral
TabletOral
SolutionOral20 mg
Tablet, chewableOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0141 mg/mLALOGPS
logP3.7ALOGPS
logP2.79ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)9.74ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.73 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity114.58 m3·mol-1ChemAxon
Polarizability44.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9916
Blood Brain Barrier+0.9314
Caco-2 permeable-0.5973
P-glycoprotein substrateSubstrate0.8692
P-glycoprotein inhibitor IInhibitor0.5895
P-glycoprotein inhibitor IINon-inhibitor0.8347
Renal organic cation transporterNon-inhibitor0.7496
CYP450 2C9 substrateNon-substrate0.8928
CYP450 2D6 substrateNon-substrate0.8126
CYP450 3A4 substrateSubstrate0.5721
CYP450 1A2 substrateNon-inhibitor0.6663
CYP450 2C9 inhibitorNon-inhibitor0.7521
CYP450 2D6 inhibitorNon-inhibitor0.7862
CYP450 2C19 inhibitorInhibitor0.5746
CYP450 3A4 inhibitorNon-inhibitor0.5286
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5396
Ames testAMES toxic0.6766
CarcinogenicityNon-carcinogens0.7628
BiodegradationNot ready biodegradable0.8614
Rat acute toxicity2.6773 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5217
hERG inhibition (predictor II)Inhibitor0.6969
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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
  1. 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]
  2. 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
  1. 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]
  2. 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
  1. 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]
  2. 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 on January 19, 2011 23:47 / Updated on June 16, 2021 12:31