Identification
- Summary
Alizapride is a dopamine antagonist used to prevent nausea and vomiting associated with medical procedures, surgeries, and cancer therapies.
- Generic Name
- Alizapride
- DrugBank Accession Number
- DB01425
- Background
Alizapride is a dopamine antagonist that is capable of demonstrating both prokinetic and antiemetic effects. This kind of pharmacological activity makes it effective for use in the treatment of various kinds of nausea and vomiting, including that which may occur postoperatively.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Alizapride (DB01425)
- Weight
- Average: 315.3702
Monoisotopic: 315.169524941 - Chemical Formula
- C16H21N5O2
- Synonyms
- Alizaprida
- Alizapride
- Alizapridum
Pharmacology
- Indication
Alizapride is used in the treatment of nausea and vomiting, including postoperative nausea and vomiting.
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- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Alizapride is a dopamine antagonist.
- Mechanism of action
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 stimuli. Structurally similar to metoclopramide and, therefore, shares similar other atributres related to emesis and prokinetics.
Target Actions Organism ADopamine D2 receptor antagonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
renal
- Half-life
3 hours
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareApomorphine The therapeutic efficacy of Apomorphine can be decreased when used in combination with Alizapride. Aripiprazole The therapeutic efficacy of Aripiprazole can be decreased when used in combination with Alizapride. Benzatropine The risk or severity of adverse effects can be increased when Alizapride is combined with Benzatropine. Brexpiprazole The therapeutic efficacy of Brexpiprazole can be decreased when used in combination with Alizapride. Bromocriptine The therapeutic efficacy of Bromocriptine can be decreased when used in combination with Alizapride. Cabergoline The therapeutic efficacy of Cabergoline can be decreased when used in combination with Alizapride. Deutetrabenazine The risk or severity of adverse effects can be increased when Alizapride is combined with Deutetrabenazine. Dihydroergocornine The therapeutic efficacy of Dihydroergocornine can be decreased when used in combination with Alizapride. Dihydroergotamine The therapeutic efficacy of Dihydroergotamine can be decreased when used in combination with Alizapride. Dopexamine The therapeutic efficacy of Dopexamine can be decreased when used in combination with Alizapride. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Alizapride hydrochloride 41BT72BOQ7 59338-87-3 BRECEDGYMYXGNF-UHFFFAOYSA-N - International/Other Brands
- Limican / Plitican (Delagrange) / Vergentan (Delagrange)
Categories
- ATC Codes
- A03FA05 — Alizapride
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzotriazoles
- Sub Class
- Not Available
- 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 show 2 more
- Substituents
- 1,2,3-triazole / Alkyl aryl ether / Amine / Amino acid or derivatives / Anisole / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Benzotriazole show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- P55703ZRZY
- CAS number
- 59338-93-1
- InChI Key
- 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
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
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0015494
- PubChem Compound
- 43008
- PubChem Substance
- 46505555
- ChemSpider
- 39202
- BindingDB
- 50023804
- 17311
- ChEBI
- 94316
- ChEMBL
- CHEMBL290194
- PharmGKB
- PA164744894
- Wikipedia
- Alizapride
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Breast Cancer 1 4 Completed Treatment Nausea / Vomiting 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Oral 12 mg Injection, solution Intramuscular; Intravenous 50 MG/2ML Solution / drops 30 ML Suppository 50 MG Solution / drops Suppository Tablet Oral Solution Intramuscular; Intravenous 50 mg Tablet Oral 50 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 139 °C 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. logP 1.79 MANNHOLD,R ET AL. (1990) - Predicted Properties
Property Value Source Water Solubility 0.495 mg/mL ALOGPS logP 1.81 ALOGPS logP 1.13 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 9.11 Chemaxon pKa (Strongest Basic) 7.77 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 83.14 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 89.21 m3·mol-1 Chemaxon Polarizability 33.92 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9563 Caco-2 permeable - 0.5816 P-glycoprotein substrate Substrate 0.7178 P-glycoprotein inhibitor I Non-inhibitor 0.5536 P-glycoprotein inhibitor II Non-inhibitor 0.7634 Renal organic cation transporter Inhibitor 0.5368 CYP450 2C9 substrate Non-substrate 0.8211 CYP450 2D6 substrate Non-substrate 0.7443 CYP450 3A4 substrate Substrate 0.6016 CYP450 1A2 substrate Non-inhibitor 0.6904 CYP450 2C9 inhibitor Non-inhibitor 0.6834 CYP450 2D6 inhibitor Non-inhibitor 0.7388 CYP450 2C19 inhibitor Non-inhibitor 0.5988 CYP450 3A4 inhibitor Inhibitor 0.5501 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7233 Ames test AMES toxic 0.5582 Carcinogenicity Non-carcinogens 0.8798 Biodegradation Not ready biodegradable 0.9597 Rat acute toxicity 2.5855 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.7771 hERG inhibition (predictor II) Inhibitor 0.628
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Drug created at July 24, 2007 11:49 / Updated at March 03, 2023 17:45