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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015494
Secondary Accession Numbers
  • HMDB15494
Metabolite Identification
Common NameAlizapride
DescriptionAlizapride 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 stimuli. Structurally similar to metoclopramide and, therefore, shares similar other atributres related to emesis and prokinetics.
Structure
Data?1582753303
Synonyms
ValueSource
PliticanKegg
N-((1-Allyl-2-pyrrolidinyl)methyl)-6-methoxy-1H-benzotriazole-5-carboxamideHMDB
LiticanHMDB
N-((Allyl-1-pyrrolidinyl-2)-methyl)methoxy-2-azimido-4,5-benzamideHMDB
VergentanHMDB
Alizapride hydrochlorideHMDB
N-(1-Allyl-2-pyrrolidinylmethyl)-6-methoxy-1H-benzotriazole-5-carboxamide hydrochlorideHMDB
Chemical FormulaC16H21N5O2
Average Molecular Weight315.3702
Monoisotopic Molecular Weight315.169524941
IUPAC Name6-methoxy-N-{[1-(prop-2-en-1-yl)pyrrolidin-2-yl]methyl}-2H-1,2,3-benzotriazole-5-carboxamide
Traditional Namealizapride
CAS Registry Number59338-93-1
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 KeyKSEYRUGYKHXGFW-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point139 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.5 g/LNot Available
LogP1.79MANNHOLD,R ET AL. (1990)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.5 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.21 m³·mol⁻¹ChemAxon
Polarizability33.92 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+175.14631661259
DarkChem[M-H]-174.35931661259
DeepCCS[M+H]+164.98430932474
DeepCCS[M-H]-162.62630932474
DeepCCS[M-2H]-195.51230932474
DeepCCS[M+Na]+171.07730932474
AllCCS[M+H]+175.932859911
AllCCS[M+H-H2O]+172.732859911
AllCCS[M+NH4]+178.832859911
AllCCS[M+Na]+179.632859911
AllCCS[M-H]-176.332859911
AllCCS[M+Na-2H]-176.332859911
AllCCS[M+HCOO]-176.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlizaprideCOC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C3822.3Standard polar33892256
AlizaprideCOC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C2630.1Standard non polar33892256
AlizaprideCOC1=CC2=NNN=C2C=C1C(=O)NCC1CCCN1CC=C3120.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alizapride,1TMS,isomer #1C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC2968.7Semi standard non polar33892256
Alizapride,1TMS,isomer #1C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC2803.1Standard non polar33892256
Alizapride,1TMS,isomer #1C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC4232.7Standard polar33892256
Alizapride,1TMS,isomer #2C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C2895.7Semi standard non polar33892256
Alizapride,1TMS,isomer #2C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C2898.8Standard non polar33892256
Alizapride,1TMS,isomer #2C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C4048.8Standard polar33892256
Alizapride,2TMS,isomer #1C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC)[Si](C)(C)C2943.4Semi standard non polar33892256
Alizapride,2TMS,isomer #1C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC)[Si](C)(C)C2813.1Standard non polar33892256
Alizapride,2TMS,isomer #1C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C)N=C2C=C1OC)[Si](C)(C)C3921.3Standard polar33892256
Alizapride,1TBDMS,isomer #1C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC3125.6Semi standard non polar33892256
Alizapride,1TBDMS,isomer #1C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC3022.8Standard non polar33892256
Alizapride,1TBDMS,isomer #1C=CCN1CCCC1CNC(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC4182.0Standard polar33892256
Alizapride,1TBDMS,isomer #2C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C(C)(C)C3112.7Semi standard non polar33892256
Alizapride,1TBDMS,isomer #2C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C(C)(C)C3115.6Standard non polar33892256
Alizapride,1TBDMS,isomer #2C=CCN1CCCC1CN(C(=O)C1=CC2=N[NH]N=C2C=C1OC)[Si](C)(C)C(C)(C)C4106.2Standard polar33892256
Alizapride,2TBDMS,isomer #1C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC)[Si](C)(C)C(C)(C)C3313.6Semi standard non polar33892256
Alizapride,2TBDMS,isomer #1C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC)[Si](C)(C)C(C)(C)C3229.0Standard non polar33892256
Alizapride,2TBDMS,isomer #1C=CCN1CCCC1CN(C(=O)C1=CC2=NN([Si](C)(C)C(C)(C)C)N=C2C=C1OC)[Si](C)(C)C(C)(C)C3889.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alizapride GC-MS (Non-derivatized) - 70eV, Positivesplash10-01rl-7981000000-7be855eb3fbb5813cbe62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alizapride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Alizapride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 10V, Positive-QTOFsplash10-014i-1938000000-1a8af33956ed83ccdece2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 20V, Positive-QTOFsplash10-00fu-4910000000-aab60443fb8b77f05e642016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 40V, Positive-QTOFsplash10-0006-9200000000-8ff3b2c5e6b60b7692c72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 10V, Negative-QTOFsplash10-03di-0219000000-52729b51e26559af4d4f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 20V, Negative-QTOFsplash10-01wv-0491000000-3e6ef639690f6aafb33f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 40V, Negative-QTOFsplash10-0037-4920000000-327c228d69462d85a4df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 10V, Positive-QTOFsplash10-014i-3209000000-58fb28ddbca5a2bd78062021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 20V, Positive-QTOFsplash10-01di-9764000000-219629153c84cf4e816c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 40V, Positive-QTOFsplash10-05o1-9300000000-f5d279616c5960f4e5962021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 10V, Negative-QTOFsplash10-03di-0009000000-da585dbe03591bbbac5d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 20V, Negative-QTOFsplash10-01r5-2942000000-c37a4ccd7bec058b80cf2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alizapride 40V, Negative-QTOFsplash10-01u9-3910000000-0acbb871a78aa32d1c732021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01425 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01425 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01425
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID39202
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlizapride
METLIN IDNot Available
PubChem Compound43008
PDB IDNot Available
ChEBI ID157186
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot 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 ]