Basic information
- CAS
23672-07-3- Standard SMILES
CCN1CCC[C@H]1CNC(=O)c1cc(S(N)(=O)=O)ccc1OC- InChIKey
BGRJTUBHPOOWDU-NSHDSACASA-N- Molecular formula
- C15H23N3O4S
- Average molar mass
- 341.4 g/mol
- Monoisotopic mass
- 341.14092722
Overview
(S)-(-)-sulpiride is an 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 M at D2, D3, D4, D1 and D5 receptors respectively). It has a role as an antidepressant, an antipsychotic agent, a dopaminergic antagonist and an antiemetic. It is an enantiomer of a (R)-(+)-sulpiride.
Names & identifiers
- Preferred name
- Levosulpiride
- IUPAC
- N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-2-methoxy-5-sulfamoylbenzamide
- English name
- Levosulpiride
- Molecular formula
- C15H23N3O4S
- Molecular weight
- 341.43
Names & synonyms
Levosulpiride23672-07-3(-)-SulpirideLevopraidLevoprideL-SulpirideLevosulpiridaLevobrenlesurideLevosulpiridumSulpiride, (s)-Sulpiride, (-)-
Show more names
Levosulpridel-Formrv-12309l-Sulpiridlevosupride(S)-(-)-Sulpir
JTG7R315LK(-)-N-(((S)-1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamide(S)-(-)-N-((1-Ethyl-2-pyrrolidinyl)methyl)-5-sulfamoyl-o-anisamideS-(-)-N-(1-Ethyl-2-pyrrolidinomethyl)-2-methoxy-5-sulfamoylebenzamideCHEBI:64119Sulpiride l-RefChem:153234N05AL07
Database identifiers
- CAS
23672-07-3- PubChem CID
- 688272
- DTXSID
DTXSID0042583- ChEMBL
CHEMBL267044- ChEBI
CHEBI:64119- UNII
- JTG7R315LK
- EC Number
- 682-417-3
- Nikkaji
- J60.441K
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 110 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 505
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 183 · 183-186 °C(lit.)
- Density
- 1.236 · 1.236±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- DMF (Slightly), DMSO (Slightly), Methanol (Slightly)
- pka
- 9.98 · 9.98±0.60(Predicted)
- form
- Solid
- color
- White to Off-White
- Merck
- 14 · 14,8989
- Major Application
- forensics and toxicologypharmaceutical (small molecule)
- 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)/t11-/m0/s1
- InChIKey
- BGRJTUBHPOOWDU-NSHDSACASA-N
- SMILES
- CCN1CCC[C@H]1CNC(=O)c2cc(ccc2OC)S(N)(=O)=O
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- BZ3400100
- ridadr
- 3077
- hs_code
- 29350090
- Toxicity
- LD50 oral in rabbit: > 1500mg/kg
- Storage Class
- 10 - Combustible liquids
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >2500
Applications
Usesdopamine receptor antagonists
UsesDopamine D2 and D3-receptor antagonist. Antipsychotic; antidepressant; antiemetic.
Uses(S)-()-Sulpiride was used to study the effect of dopamine D2 receptor function on activation of KCNQ potassium channels10 and on depression-like behavior in ovariectomized female rats.11
General Description(S)-()-Sulpiride is a levorotatory enantiomer of sulpiride, which shows greater central antidopaminergic activity, antiemetic and antidyspeptic effects. It is also used as a therapeutic drug for the treatment of depression and somatoform disorders.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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