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Record Information
Version4.0
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-09-27 08:27:35 UTC
HMDB IDHMDB0014535
Secondary Accession Numbers
  • HMDB14535
Metabolite Identification
Common NameSulpiride
DescriptionSulpiride is only found in individuals that have used or taken this drug. It is a dopamine D2-receptor antagonist. It has been used therapeutically as an antidepressant, antipsychotic, and as a digestive aid. (From Merck Index, 11th ed)In contrast to most other neuroleptics which block both dopamine D1 and D2 receptors, Sulpiride is more selective and acts primarily as a dopamine D2 antagonist. Sulpiride appears to lack effects on norepinephrine, acetylcholine, serotonin, histamine, or gamma-aminobutyric acid (GABA) receptors.
Structure
Thumb
Synonyms
ValueSource
(+-)-SulpirideChEBI
5-(Aminosulfonyl)-N-((1-ethyl-2-pyrrolidinyl)methyl)-2-methoxybenzamideChEBI
N-((1-Ethyl-2-pyrrolidinyl)methyl)-2-methoxy-5-sulfamoylbenzamideChEBI
N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-O-anisamideChEBI
SulpiridChEBI
SulpiridaChEBI
SulpiridumChEBI
SulpyridChEBI
5-(Aminosulphonyl)-N-((1-ethyl-2-pyrrolidinyl)methyl)-2-methoxybenzamideGenerator
N-((1-Ethyl-2-pyrrolidinyl)methyl)-2-methoxy-5-sulphamoylbenzamideGenerator
N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulphamoyl-O-anisamideGenerator
LevosulpirideHMDB
Areu brand OF sulpirideMeSH
EglonylMeSH
Hexal brand OF sulpirideMeSH
PsicocenMeSH
Sanofi synthelabo brand OF sulpirideMeSH
vertigo NeogamaMeSH
Almirall brand OF sulpirideMeSH
ArminolMeSH
Desitin brand OF sulpirideMeSH
Dolorgiet brand OF sulpirideMeSH
EkilidMeSH
Erempharma brand OF sulpirideMeSH
LeboprideMeSH
Sanofi-synthelabo brand OF sulpirideMeSH
SulpMeSH
SulperideMeSH
SulpitilMeSH
SulporMeSH
Uriach brand OF sulpirideMeSH
vertigo-MeresaMeSH
vertigo-NeogamaMeSH
AiglonylMeSH
DeponertonMeSH
DesisulpidMeSH
DogmatilMeSH
DolmatilMeSH
Fumouzer brand OF sulpirideMeSH
Hennig brand OF sulpirideMeSH
Hoechst brand OF sulpirideMeSH
Pharmacia brand OF sulpirideMeSH
PontirideMeSH
Psicofarma brand OF sulpirideMeSH
Spyfarma brand OF sulpirideMeSH
SynédilMeSH
NeogamaMeSH
Allphar brand OF sulpirideMeSH
Centrum brand OF sulpirideMeSH
DigtonMeSH
GuastilMeSH
Hormosan brand OF sulpirideMeSH
Krewel brand OF sulpirideMeSH
MeresaMeSH
Rosemont brand OF sulpirideMeSH
SulpivertMeSH
TepavilMeSH
vertigo MeresaMeSH
Chemical FormulaC15H23N3O4S
Average Molecular Weight341.426
Monoisotopic Molecular Weight341.140926929
IUPAC NameN-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide
Traditional Namesulpiride
CAS Registry Number15676-16-1
SMILES
CCN1CCCC1CNC(=O)C1=C(OC)C=CC(=C1)S(N)(=O)=O
InChI Identifier
InChI=1S/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)
InChI KeyBGRJTUBHPOOWDU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Organosulfonic acid amide
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Azacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organosulfur compound
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.54 g/LNot Available
LogP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP1.2ALOGPS
logP0.22ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.24ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area101.73 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity88.63 m³·mol⁻¹ChemAxon
Polarizability36.18 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03di-3972000000-4f53a77ce37004c9eac3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0109000000-838e3fc396f400ef6f4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-2901000000-15575a206ad43d931d6aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-3900000000-b83b6287d83301602f00View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a6r-8900000000-5a447dc363e7b3d43351View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9200000000-0a29790b32c5ae5e192aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-004i-9000000000-32eb95f9c75cc8d8ee85View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0009000000-b451c07c9adbe534b75cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-0049000000-eaadc21e5bafdd34a66eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-16b776d58e4e2dbc163eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0090000000-9fda88d7482dee887457View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0009000000-338379e29df68a5396b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0006-0209000000-d61c87359158078fa846View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-2931000000-6a28d0dd33433a572e50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-4940000000-dcee56e4387108740566View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03di-8960000000-9f1a7605079446735287View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03e9-9620000000-c3bb475e828d5f8c88aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-3972000000-4f53a77ce37004c9eac3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0519000000-709a0cc07372655e216eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-2931000000-a4feed04814e6a775edbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qm-9300000000-41411c150a46fffcffd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019000000-908ca17fb0c5d8ea4da3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6936000000-913d80650e823e5a057cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210000000-e9d0ec345582ac120e35View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00391 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00391 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00391
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5162
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulpiride
METLIN IDNot Available
PubChem Compound5355
PDB IDNot Available
ChEBI ID32168
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Vacca C, Maione S, Tozzi A, Marmo E: Benzamides and cholinesterases. Res Commun Chem Pathol Pharmacol. 1987 Feb;55(2):193-201. [PubMed:3823608 ]
  2. Dross K: [The relevance of anticholinesterase properties to toxicity and neuromuscular effects of sulpiride (author's transl)]. Arzneimittelforschung. 1977 Feb;27(2):404-6. [PubMed:577162 ]
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. Cavallotti C, Nuti F, Bruzzone P, Mancone M: Age-related changes in dopamine D2 receptors in rat heart and coronary vessels. Clin Exp Pharmacol Physiol. 2002 May-Jun;29(5-6):412-8. [PubMed:12010185 ]
  2. Jaber M, Tison F, Fournier MC, Bloch B: Differential influence of haloperidol and sulpiride on dopamine receptors and peptide mRNA levels in the rat striatum and pituitary. Brain Res Mol Brain Res. 1994 Apr;23(1-2):14-20. [PubMed:7518029 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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. Promotes cell proliferation
Gene Name:
DRD3
Uniprot ID:
P35462
Molecular weight:
44224.3
References
  1. Lipina TV, Vishnivetskaia GB: [Effect of sulpiride on immobility reflex and pinch-induced catalepsy in CBA/Lac male mice with various social status]. Zh Vyssh Nerv Deiat Im I P Pavlova. 2009 Jul-Aug;59(4):482-7. [PubMed:19795811 ]
  2. Collo G, Zanetti S, Missale C, Spano P: Dopamine D3 receptor-preferring agonists increase dendrite arborization of mesencephalic dopaminergic neurons via extracellular signal-regulated kinase phosphorylation. Eur J Neurosci. 2008 Oct;28(7):1231-40. doi: 10.1111/j.1460-9568.2008.06423.x. [PubMed:18973551 ]