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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:52 UTC
HMDB IDHMDB14535
Secondary Accession NumbersNone
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
LevosulpirideHMDB
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 KeyInChIKey=BGRJTUBHPOOWDU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Salicylamide
  • Benzenesulfonamide
  • Benzoic acid or derivatives
  • Benzamide
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • N-alkylpyrrolidine
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Pyrrolidine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antidepressants
  • Antidepressive Agents, Second-Generation
  • Antipsychotic Agents
  • Antipsychotics
  • Dopamine Antagonists
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point178 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.37e-01 g/LNot Available
LogP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.54 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity88.63 m3·mol-1ChemAxon
Polarizability36.18 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00391
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00391
  • Not Applicable
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
NuGOwiki LinkHMDB14535
Metagene LinkHMDB14535
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. [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. [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. [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. [7518029 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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. [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. [18973551 ]