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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
SaltsNot Available
Brand names
NameCompany
BlastonNot Available
CinmoveNot Available
CintaproNot Available
PaxaprideNot Available
PemixNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentNitrophenols and Derivatives
Alternative parentsSalicylamides; Nitrobenzenes; Aminobenzamides; Benzoyl Derivatives; Phenol Ethers; Alkyl Aryl Ethers; Aminopiperidines; Anilines; Primary Aromatic Amines; Nitro Compounds; Secondary Carboxylic Acid Amides; Nitronic Acids; Tertiary Amines; Carboxylic Acids; Enolates; Polyamines; Organic Oxoazanium Compounds
Substituentsphenol ether; benzoyl; aniline; alkyl aryl ether; 4-aminopiperidine; primary aromatic amine; piperidine; carboxamide group; nitronic acid; tertiary amine; nitro compound; secondary carboxylic acid amide; organic oxoazanium; carboxylic acid; polyamine; ether; enolate; carboxylic acid derivative; amine; organonitrogen compound; primary amine
Classification descriptionThis compound belongs to the nitrophenols and derivatives. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both an hydroxyl group and a nitro group on two different ring carbon atoms.
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
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 substrate Non-inhibitor 0.7521
CYP450 2D6 substrate Non-inhibitor 0.7862
CYP450 2C19 substrate Inhibitor 0.5746
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
TabletOral1mg
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility1.41e-02 g/lALOGPS
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 area113.41ChemAxon
rotatable bond count7ChemAxon
refractivity115.58ChemAxon
polarizability44.29ChemAxon
number of rings3ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
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
ResourceLink
KEGG DrugD07700
PharmGKBPA165958427
WikipediaCinitapride
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