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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2021-09-14 15:47:32 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
Data?1582753190
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
DogmatylKegg
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, HMDB
EglonylMeSH, HMDB
Hexal brand OF sulpirideMeSH, HMDB
PsicocenMeSH, HMDB
Sanofi synthelabo brand OF sulpirideMeSH, HMDB
vertigo NeogamaMeSH, HMDB
Almirall brand OF sulpirideMeSH, HMDB
ArminolMeSH, HMDB
Desitin brand OF sulpirideMeSH, HMDB
Dolorgiet brand OF sulpirideMeSH, HMDB
EkilidMeSH, HMDB
Erempharma brand OF sulpirideMeSH, HMDB
LeboprideMeSH, HMDB
Sanofi-synthelabo brand OF sulpirideMeSH, HMDB
SulpMeSH, HMDB
SulperideMeSH, HMDB
SulpitilMeSH, HMDB
SulporMeSH, HMDB
Uriach brand OF sulpirideMeSH, HMDB
vertigo-MeresaMeSH, HMDB
vertigo-NeogamaMeSH, HMDB
AiglonylMeSH, HMDB
DeponertonMeSH, HMDB
DesisulpidMeSH, HMDB
DogmatilMeSH, HMDB
DolmatilMeSH, HMDB
Fumouzer brand OF sulpirideMeSH, HMDB
Hennig brand OF sulpirideMeSH, HMDB
Hoechst brand OF sulpirideMeSH, HMDB
Pharmacia brand OF sulpirideMeSH, HMDB
PontirideMeSH, HMDB
Psicofarma brand OF sulpirideMeSH, HMDB
Spyfarma brand OF sulpirideMeSH, HMDB
SynédilMeSH, HMDB
NeogamaMeSH, HMDB
Allphar brand OF sulpirideMeSH, HMDB
Centrum brand OF sulpirideMeSH, HMDB
DigtonMeSH, HMDB
GuastilMeSH, HMDB
Hormosan brand OF sulpirideMeSH, HMDB
Krewel brand OF sulpirideMeSH, HMDB
MeresaMeSH, HMDB
Rosemont brand OF sulpirideMeSH, HMDB
SulpivertMeSH, HMDB
TepavilMeSH, HMDB
vertigo MeresaMeSH, HMDB
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
Description Belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.54 g/LNot Available
LogP0.6Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM184.330932474
AllCCS[M+H]+Not Available183.271http://allccs.zhulab.cn/database/detail?ID=AllCCS00000726
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP10(1.2) g/LALOGPS
logP10(0.22) g/LChemAxon
logS10(-2.8) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+182.08831661259
DarkChem[M-H]-179.43431661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulpiride GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-9051000000-fc43a13ec398aad888f42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulpiride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulpiride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-qTof , Positive-QTOFsplash10-03di-3972000000-4f53a77ce37004c9eac32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , negative-QTOFsplash10-0006-0109000000-838e3fc396f400ef6f4b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , negative-QTOFsplash10-0a4i-2901000000-15575a206ad43d931d6a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , negative-QTOFsplash10-0a4i-3900000000-b83b6287d83301602f002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , negative-QTOFsplash10-0a6r-8900000000-5a447dc363e7b3d433512017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , negative-QTOFsplash10-004i-9200000000-0a29790b32c5ae5e192a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , negative-QTOFsplash10-004i-9000000000-32eb95f9c75cc8d8ee852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QTOF , positive-QTOFsplash10-0006-0009000000-b451c07c9adbe534b75c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QTOF , positive-QTOFsplash10-01ox-0049000000-eaadc21e5bafdd34a66e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QTOF , positive-QTOFsplash10-03di-0090000000-16b776d58e4e2dbc163e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QTOF , positive-QTOFsplash10-03di-0090000000-9fda88d7482dee8874572017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , positive-QTOFsplash10-0006-0009000000-338379e29df68a5396b72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , positive-QTOFsplash10-0006-0209000000-d61c87359158078fa8462017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , positive-QTOFsplash10-03di-2931000000-6a28d0dd33433a572e502017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , positive-QTOFsplash10-03di-4940000000-dcee56e43871087405662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , positive-QTOFsplash10-03di-8960000000-9f1a76050794467352872017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride LC-ESI-QFT , positive-QTOFsplash10-03e9-9620000000-c3bb475e828d5f8c88aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride , positive-QTOFsplash10-03di-3972000000-4f53a77ce37004c9eac32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulpiride 60V, Positive-QTOFsplash10-03di-4940000000-9b2cb139fd5f8b5aacec2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulpiride 10V, Positive-QTOFsplash10-01ox-0519000000-709a0cc07372655e216e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulpiride 20V, Positive-QTOFsplash10-03fr-2931000000-a4feed04814e6a775edb2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulpiride 40V, Positive-QTOFsplash10-01qm-9300000000-41411c150a46fffcffd52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulpiride 10V, Negative-QTOFsplash10-0006-0019000000-908ca17fb0c5d8ea4da32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulpiride 20V, Negative-QTOFsplash10-01t9-6936000000-913d80650e823e5a057c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulpiride 40V, Negative-QTOFsplash10-004i-9210000000-e9d0ec345582ac120e352016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00391 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00391 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00391
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5162
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulpiride
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID32168
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 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 ]