IDPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomy
Targets (3)
Targets (3)Biointeractions (3)

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Identification
NameCinitapride
Accession NumberDB08810
TypeSmall Molecule
GroupsApproved
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
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Paxapride
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BlastonNot Available
CinmoveNot Available
CintaproNot Available
PaxaprideNot Available
PemixNot Available
Brand mixturesNot Available
Categories
UNIIR8I97I2L24
CAS number66564-14-5
WeightAverage: 402.4873
Monoisotopic: 402.226705468
Chemical FormulaC21H30N4O4
InChI KeyZDLBNXXKDMLZMF-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-ylmethyl)piperidin-4-yl]-2-ethoxy-5-nitrobenzamide
SMILES
CCOC1=CC(N)=C(C=C1C(=O)NC1CCN(CC2CCC=CC2)CC1)[N+]([O-])=O
Pharmacology
Indication

For the treatment of gastrointestinal disorders associated with motility disturbances such as gastroesophageal reflux disease, non-ulcer dyspepsia and delayed gastric emptying.

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action

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

TargetKindPharmacological actionActionsOrganismUniProt ID
5-hydroxytryptamine receptor 1AProteinyes
agonist
HumanP08908 details
5-hydroxytryptamine receptor 2AProteinyes
antagonist
HumanP28223 details
5-hydroxytryptamine receptor 4Proteinunknown
agonist
HumanQ13639 details
Related Articles
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 distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life

3-5 h during the first 8 h and a residual half-life greater than 15 h thereafter.

ClearanceNot Available
Toxicity

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

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
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. [PubMed:9211565 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentIndigestion1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0141 mg/mLALOGPS
logP3.7ALOGPS
logP2.79ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.89ChemAxon
pKa (Strongest Basic)9.74ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area113.41 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity115.58 m3·mol-1ChemAxon
Polarizability44.29 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as nitrophenyl ethers. These are aromatic compounds containing a nitrobenzene moiety that carries an ether group on the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentNitrophenyl ethers
Alternative ParentsAminobenzamides / Aminophenyl ethers / Benzamides / Phenoxy compounds / Aniline and substituted anilines / Nitroaromatic compounds / Benzoyl derivatives / Alkyl aryl ethers / Primary aromatic amines / Piperidines
SubstituentsNitrophenyl ether / Aminobenzamide / Aminobenzoic acid or derivatives / Aminophenyl ether / Benzamide / Benzoic acid or derivatives / Phenoxy compound / Nitroaromatic compound / Aniline or substituted anilines / Benzoyl
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

Details
1. 5-hydroxytryptamine receptor 1A
Kind
Protein
Organism
Human
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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
Gene Name:
HTR1A
Uniprot ID:
P08908
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. [PubMed:9211565 ]
  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. [PubMed:9562338 ]
Details
2. 5-hydroxytryptamine receptor 2A
Kind
Protein
Organism
Human
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-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
Gene Name:
HTR2A
Uniprot ID:
P28223
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. [PubMed:9211565 ]
  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. [PubMed:9562338 ]
Details
3. 5-hydroxytryptamine receptor 4
Kind
Protein
Organism
Human
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 is mediated by G proteins that stimulate adenylate cyclase.
Gene Name:
HTR4
Uniprot ID:
Q13639
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. [PubMed:9211565 ]
  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. [PubMed:9562338 ]
Drug created on January 19, 2011 16:47 / Updated on June 11, 2017 17:11