You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:55:27 UTC
Update Date2019-07-23 06:35:24 UTC
HMDB IDHMDB0042039
Secondary Accession Numbers
  • HMDB42039
Metabolite Identification
Common NameTiapride
DescriptionTiapride, also known as tiapridal or equilium, belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group. Tiapride is a very strong basic compound (based on its pKa). It has been used as an antipsychotic and in the treatment of various movement disorders and alcoholism. Tiapride is minimally metabolized in humans, 70 % of the drug is eliminated in unchanged form in the urine within 24 hours. Tiapride is a selective dopamine D2 and D3 receptor antagonist, offering an advantage over other neuroleptic drugs, such as haloperidol and risperidone, which bind a range of targets including four of the five known dopamine receptor subtypes (D1-4), serotonin (5-HT2A, 2C), α1- and α2-adrenergic, and histamine H1 receptors. One study found that tiapride shows over three times as much affinity for limbic areas than striatal areas as opposed to the near equal selectivity for limbic and striatal regions shown by haloperidol. Tiapride has a high degree of regional selectivity for limbic areas. Compared to these drugs, tiapride has a relatively moderate affinity for its target receptors, displacing 50 percent of 3H-raclopride binding at a concentration of 320 nM at D2 receptors and a concentration of 180 nM at D3 receptors. Only low concentration of N-desethyl tiapride and tiapride N-oxide and no phase II metabolites were detected. Efficacy at the D2 receptor is moderate, with 80 percent of receptors occupied even in the presence of excess tiapride concentrations.
Structure
Data?1563863724
Synonyms
ValueSource
TiapridalKegg
Tiapride hydrochlorideHMDB
EquiliumHMDB
Hydrochloride, tiaprideHMDB
Monohydrochloride, tiaprideHMDB
TiapridexHMDB
Tiapride monohydrochlorideHMDB
TiaprizalHMDB
Chemical FormulaC15H24N2O4S
Average Molecular Weight328.427
Monoisotopic Molecular Weight328.145677956
IUPAC NameN-[2-(diethylamino)ethyl]-5-methanesulfonyl-2-methoxybenzene-1-carboximidic acid
Traditional Nametiapride
CAS Registry Number51012-32-9
SMILES
CCN(CC)CCN=C(O)C1=C(OC)C=CC(=C1)S(C)(=O)=O
InChI Identifier
InChI=1S/C15H24N2O4S/c1-5-17(6-2)10-9-16-15(18)13-11-12(22(4,19)20)7-8-14(13)21-3/h7-8,11H,5-6,9-10H2,1-4H3,(H,16,18)
InChI KeyJTVPZMFULRWINT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonyl compounds
Direct ParentBenzenesulfonyl compounds
Alternative Parents
Substituents
  • Benzenesulfonyl group
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Sulfone
  • Sulfonyl
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point124 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.90Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.55ALOGPS
logP0.68ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.46ChemAxon
pKa (Strongest Basic)8.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area79.2 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity88.54 m³·mol⁻¹ChemAxon
Polarizability35.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000j-8292000000-edf72e41d8713a9c720fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000i-7019000000-899f716f2da558cdf38fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4r-2900000000-ce7cf18c3df7664007c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-2900000000-f2c792ada2d697b7a343Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-5900000000-660415070e12bcbe4376Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a6r-9700000000-2ce26990c6212c2ed171Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01t9-9200000000-8d71048d6039798257ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01t9-9000000000-128e0b213532d5c3e6b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-004i-0009000000-da514094cabb39732203Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0091000000-c4544a176e5242fdbb7fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0a4i-0090000000-fb4e4eea413d32fc6219Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-08fr-0190000000-90bc8da6d92687ec2d7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-0690000000-37fc0504835723e81e17Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-1930000000-612cdc3e15572ae24953Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1439000000-e604f143418a5e26ed28Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pvi-5891000000-97a02f864c0501ccc501Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fk9-9410000000-a2bf0c23a9484bd3dde1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1019000000-73c774e3942279a08485Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9345000000-820f6d565d65c6e470acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-4861c4710a8a5e9fb445Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB13025
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5268
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTiapride
METLIN IDNot Available
PubChem Compound5467
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available