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Alizapride

July 24, 2017
Common Name

Alizapride Description

Alizapride is only found in individuals that have used or taken this drug. It is a dopamine antagonist with prokinetic and antiemetic effects used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.The 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 stimlii. Structurally similar to metoclopramide and, therefore, shares similar other atributres related to emesis and prokinetics. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source PliticanKegg N-((1-Allyl-2-pyrrolidinyl)methyl)-6-methoxy-1H-benzotriazole-5-carboxamideMeSH LiticanMeSH N-((Allyl-1-pyrrolidinyl-2)-methyl)methoxy-2-azimido-4,5-benzamideMeSH VergentanMeSH Alizapride hydrochlorideMeSH

Chemical Formlia

C16H21N5O2 Average Molecliar Weight

315.3702 Monoisotopic Molecliar Weight

315.169524941 IUPAC Name

6-methoxy-N-{[1-(prop-2-en-1-yl)pyrrolidin-2-yl]methyl}-2H-1,2,3-benzotriazole-5-carboxamide Traditional Name

alizapride CAS Registry Number

59338-93-1 SMILES

COC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C

InChI Identifier

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)

InChI Key

KSEYRUGYKHXGFW-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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). Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Benzotriazoles Direct Parent

Benzotriazoles Alternative Parents

  • Anisoles
  • Alkyl aryl ethers
  • N-alkylpyrrolidines
  • Triazoles
  • Heteroaromatic compounds
  • Trialkylamines
  • Secondary carboxylic acid amides
  • Amino acids and derivatives
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Benzotriazole
  • Anisole
  • Alkyl aryl ether
  • N-alkylpyrrolidine
  • Benzenoid
  • Azole
  • Pyrrolidine
  • Triazole
  • 1,2,3-triazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Ether
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antiemetics
  • Prokinetic Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point139 °CNot Available Boiling PointNot AvailableNot Available Water Solubility4.95e-01 g/LNot Available LogP1.79MANNHOLD,R ET AL. (1990)

    Predicted Properties

    Property Value Source Water Solubility0.49 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01425

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01425

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01425 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    39202 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Alizapride NuGOwiki Link

    HMDB15494 Metagene Link

    HMDB15494 METLIN ID

    Not Available PubChem Compound

    43008 PDB ID

    Not Available ChEBI ID

    157186

    Product: Amiodarone

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available 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 ]

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
    Gene Name:
    DRD2
    Uniprot ID:
    P14416
    Molecular weight:
    50618.9
    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 ]

    PMID: 26337959

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