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Identification
NameAlizapride
Accession NumberDB01425
TypeSmall Molecule
GroupsApproved
Description

Alizapride is a dopamine antagonist with prokinetic and antiemetic effects used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.

Structure
Thumb
Synonyms
Alizaprida
Alizapridum
Plitican
External Identifiers 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
LimicanNot Available
PliticanDelagrange
VergentanDelagrange
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Alizapride hydrochloride
ThumbNot applicableDBSALT000918
Categories
UNIIP55703ZRZY
CAS number59338-93-1
WeightAverage: 315.3702
Monoisotopic: 315.169524941
Chemical FormulaC16H21N5O2
InChI KeyInChIKey=KSEYRUGYKHXGFW-UHFFFAOYSA-N
InChI
InChI=1S/C16H21N5O2/c1-3-6-21-7-4-5-11(21)10-17-16(22)12-8-13-14(19-20-18-13)9-15(12)23-2/h3,8-9,11H,1,4-7,10H2,2H3,(H,17,22)(H,18,19,20)
IUPAC Name
6-methoxy-N-{[1-(prop-2-en-1-yl)pyrrolidin-2-yl]methyl}-2H-1,2,3-benzotriazole-5-carboxamide
SMILES
COC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzotriazoles. These are organic compounds containing a benzene fused to a triazole ring (a five-membered ring with two carbon atoms and three nitrogen atoms).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzotriazoles
Sub ClassNot Available
Direct ParentBenzotriazoles
Alternative Parents
Substituents
  • Benzotriazole
  • Benzamide
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • N-alkylpyrrolidine
  • Heteroaromatic compound
  • 1,2,3-triazole
  • Triazole
  • Pyrrolidine
  • Azole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationAlizapride is used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.
PharmacodynamicsAlizapride is a dopamine antagonist.
Mechanism of actionThe anti-emetic action of Alizapride is due to its antagonist activity at D2 receptors in the chemoreceptor trigger zone (CTZ) in the central nervous system (CNS)—this action prevents nausea and vomiting triggered by most stimuli. Structurally similar to metoclopramide and, therefore, shares similar other atributres related to emesis and prokinetics.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationrenal
Half life3 hours
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9563
Caco-2 permeable-0.5816
P-glycoprotein substrateSubstrate0.7178
P-glycoprotein inhibitor INon-inhibitor0.5536
P-glycoprotein inhibitor IINon-inhibitor0.7634
Renal organic cation transporterInhibitor0.5368
CYP450 2C9 substrateNon-substrate0.8211
CYP450 2D6 substrateNon-substrate0.7443
CYP450 3A4 substrateSubstrate0.6016
CYP450 1A2 substrateNon-inhibitor0.6904
CYP450 2C9 inhibitorNon-inhibitor0.6834
CYP450 2D6 inhibitorNon-inhibitor0.7388
CYP450 2C19 inhibitorNon-inhibitor0.5988
CYP450 3A4 inhibitorInhibitor0.5501
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7233
Ames testAMES toxic0.5582
CarcinogenicityNon-carcinogens0.8798
BiodegradationNot ready biodegradable0.9597
Rat acute toxicity2.5855 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.7771
hERG inhibition (predictor II)Inhibitor0.628
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point139 °CBulteau, G., Acher, J., Collignon, C. and Monier, J.C.; U S . Patent 4,039,672; August 2,1977; assigned to Societe D'Etudes Scientifiques et lndustrielles de I'lle-de-France.
logP1.79MANNHOLD,R ET AL. (1990)
Predicted Properties
PropertyValueSource
Water Solubility0.495 mg/mLALOGPS
logP1.81ALOGPS
logP1.12ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.86ChemAxon
pKa (Strongest Basic)7.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.14 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.21 m3·mol-1ChemAxon
Polarizability33.92 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 Reference

Bulteau, G., Acher, J., Collignon, C. and Monier, J.C.; U S . Patent 4,039,672; August 2,1977;
assigned to Societe D’Etudes Scientifiques et lndustrielles de I’lle-de-France.

US4039672
General References
  1. Bleiberg H, Gerard B, Dalesio O, Crespeigne N, Rozencweig M: Activity of a new antiemetic agent: alizapride. A randomized double-blind crossover controlled trial. Cancer Chemother Pharmacol. 1988;22(4):316-20. [PubMed:3048762 ]
External Links
ATC CodesA03FA05
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Potassium channel regulator activity
Specific Function:
Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular Weight:
50618.91 Da
References
  1. Szelenyi I, Herold H, Gothert M: Emesis induced in domestic pigs: a new experimental tool for detection of antiemetic drugs and for evaluation of emetogenic potential of new anticancer agents. J Pharmacol Toxicol Methods. 1994 Oct;32(2):109-16. [PubMed:7865862 ]
  2. Gomez F, Ruiz P, Briceno F, Rivera C, Lopez R: Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs. Clin Immunol. 1999 Mar;90(3):375-87. [PubMed:10075867 ]
  3. Dhasmana KM, Villalon CM, Zhu YN, Parmar SS: The role of dopamine (D2), alpha and beta-adrenoceptor receptors in the decrease in gastrointestinal transit induced by dopamine and dopamine-related drugs in the rat. Pharmacol Res. 1993 May-Jun;27(4):335-47. [PubMed:8103596 ]
  4. Kilpatrick GJ, el Tayar N, Van de Waterbeemd H, Jenner P, Testa B, Marsden CD: The thermodynamics of agonist and antagonist binding to dopamine D-2 receptors. Mol Pharmacol. 1986 Sep;30(3):226-34. [PubMed:2943980 ]
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Drug created on July 24, 2007 05:49 / Updated on March 27, 2014 13:07