Levosulpiride (CHEM017833)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:40:58 UTC
Update Date2016-11-09 01:15:40 UTC
Accession NumberCHEM017833
Identification
Common NameLevosulpiride
ClassSmall Molecule
DescriptionAn optically active form of sulpiride having (S)-configuration. The active enantiomer of the racemic drug sulpiride. Selective D2-like dopamine antagonist (Ki values are ~ 0.015. ~ 0.013, 1, ~ 45 and ~ 77 muM at D2, D3, D4, D1 and D5 receptors respectively).
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(-)-SulpirideChEBI
(-)-N-(((S)-1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-O-anisamideChEBI
(S)-(-)-5-Aminosulfonyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamideChEBI
(S)-(-)-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-O-anisamideChEBI
(S)-SulpirideChEBI
LevosulpiridaChEBI
LevosulpirideChEBI
LevosulpiridumChEBI
S-(-)-N-(1-Ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoylebenzamideChEBI
LevopraidKegg
(-)-N-(((S)-1-Ethyl-2-pyrrolidinyl)methyl)-5-sulphamoyl-O-anisamideGenerator
(S)-(-)-5-Aminosulphonyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamideGenerator
(S)-(-)-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulphamoyl-O-anisamideGenerator
S-(-)-N-(1-Ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulphamoylebenzamideGenerator
N-(((S)-1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-O-anisamideMeSH
N-[[(2S)-1-Ethylpyrrolidin-2-yl]methyl]-2-methoxy-5-sulphamoylbenzamideGenerator
Chemical FormulaC15H23N3O4S
Average Molecular Mass341.430 g/mol
Monoisotopic Mass341.141 g/mol
CAS Registry Number23672-07-3
IUPAC NameN-{[(2S)-1-ethylpyrrolidin-2-yl]methyl}-2-methoxy-5-sulfamoylbenzene-1-carboximidic acid
Traditional NameS-(-)-sulpiride
SMILES[H][C@@]1(CN=C(O)C2=C(OC)C=CC(=C2)S(N)(=O)=O)CCCN1CC
InChI IdentifierInChI=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)/t11-/m0/s1
InChI KeyBGRJTUBHPOOWDU-NSHDSACASA-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
  • Benzamide
  • Benzenesulfonyl group
  • Benzoic acid or derivatives
  • Phenoxy compound
  • Anisole
  • Benzoyl
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • N-alkylpyrrolidine
  • Organosulfonic acid amide
  • Pyrrolidine
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Ether
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP1.06ALOGPS
logP-1.1ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.13ChemAxon
pKa (Strongest Basic)9.22ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area105.22 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.15 m³·mol⁻¹ChemAxon
Polarizability35.68 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0519000000-709a0cc07372655e216eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-2931000000-a4feed04814e6a775edbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01qm-9300000000-41411c150a46fffcffd5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0019000000-908ca17fb0c5d8ea4da3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6936000000-913d80650e823e5a057cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9210000000-e9d0ec345582ac120e35Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLevosulpiride
Chemspider IDNot Available
ChEBI ID64119
PubChem Compound ID688272
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18186115
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19165957
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=19452563
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19488984
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19795476
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20438811
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=20656570
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20850200
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21223496
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21615988