Alizapride

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
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 Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofNausea and vomiting•••••••••••••••••••••• ••••••••• ••••••
Symptomatic treatment ofNausea and vomiting•••••••••••••••••••••• ••••••••• ••••••
Symptomatic treatment ofNausea and vomiting•••••••••••••••••••••• ••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ADopamine D2 receptor
antagonist
Humans
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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Toxicity

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.
DrugInteraction
ApomorphineThe therapeutic efficacy of Apomorphine can be decreased when used in combination with Alizapride.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Alizapride.
BenzatropineThe risk or severity of adverse effects can be increased when Alizapride is combined with Benzatropine.
BrexpiprazoleThe therapeutic efficacy of Brexpiprazole can be decreased when used in combination with Alizapride.
BromocriptineThe therapeutic efficacy of Bromocriptine can be decreased when used in combination with Alizapride.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Alizapride hydrochloride41BT72BOQ759338-87-3BRECEDGYMYXGNF-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
  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. [Article]
Human Metabolome Database
HMDB0015494
PubChem Compound
43008
PubChem Substance
46505555
ChemSpider
39202
BindingDB
50023804
RxNav
17311
ChEBI
94316
ChEMBL
CHEMBL290194
PharmGKB
PA164744894
Wikipedia
Alizapride

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentBreast Cancer1
4CompletedTreatmentNausea / Vomiting1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular; Intravenous50 MG/2ML
Solution / drops30 ML
Suppository50 MG
TabletOral50 MG
Solution / drops
Suppository
TabletOral
SolutionIntramuscular; Intravenous50 mg
SolutionOral12 mg
TabletOral5000000 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)139 °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
logP1.13Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)9.11Chemaxon
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 RuleNoChemaxon
MDDR-like RuleYesChemaxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-01rl-7981000000-7be855eb3fbb5813cbe6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-3209000000-1ab3c3205fb5dadc7c69
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0229-0194000000-0e57fde22e055698c2cb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-032a-9775000000-f439bb32d6ef1d302fe1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0c03-1891000000-3996489c4b30955ae807
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ls-9530000000-aeec8ac9ef123c93e85a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-053u-3940000000-8e1fda6ba58d7a7cb782
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.4346147
predicted
DarkChem Lite v0.1.0
[M-H]-162.62614
predicted
DeepCCS 1.0 (2019)
[M+H]+188.1351147
predicted
DarkChem Lite v0.1.0
[M+H]+164.98412
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.3666147
predicted
DarkChem Lite v0.1.0
[M+Na]+171.07729
predicted
DeepCCS 1.0 (2019)

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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]

Drug created at July 24, 2007 11:49 / Updated at December 02, 2023 06:59