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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
Synonyms
SynonymLanguageCode
PaxaprideNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
BlastonNot Available
CinmoveNot Available
CintaproNot Available
PaxaprideNot Available
PemixNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
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
Taxonomy
ClassificationNot classified
Pharmacology
IndicationFor the treatment of gastrointestinal disorders associated with motility disturbances such as gastroesophageal reflux disease, non-ulcer dyspepsia and delayed gastric emptying.
PharmacodynamicsNot Available
Mechanism of actionCinitapride is a substituted benzamide with 5-HT receptor antagonist and agonist activity.
AbsorptionThe 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
Metabolism
Route of eliminationNot Available
Half life3-5 h during the first 8 h and a residual half-life greater than 15 h thereafter.
ClearanceNot Available
ToxicityThe symptoms of overdose include drowsiness, confusion and extrapyramidal effects.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateNon-inhibitor0.7521
CYP450 2D6 substrateNon-inhibitor0.7862
CYP450 2C19 substrateInhibitor0.5746
CYP450 3A4 substrateNon-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
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
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  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
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AtropineAnticholinergic agents like atropine may reduce the action of cinitapride.
DigoxinCinitapride can alter the absorption of digoxin as it simulates gastric emptying.
Digoxin Immune Fab (Ovine)Cinitapride can alter the absorption of digoxin as it simulates gastric emptying.
Methylscopolamine bromideAnticholinergic agents like methylscopolamine may reduce the action of cinitapride.
ScopolamineAnticholinergic agents like scopolamine may reduce the action of cinitapride.
Food InteractionsNot Available

Targets

1. 5-hydroxytryptamine receptor 1A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1A P08908 Details

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
  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

2. 5-hydroxytryptamine receptor 2A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details

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
  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

3. 5-hydroxytryptamine receptor 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 4 Q13639 Details

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
  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

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Drug created on January 19, 2011 16:47 / Updated on October 03, 2013 21:51