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S7771

Sigma-Aldrich

(S)-(−)-Sulpiride

≥98% (titration)

Synonym(s):

(S)-5-Aminosulfonyl-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide, Levosulpiride

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About This Item

Empirical Formula (Hill Notation):
C15H23N3O4S
CAS Number:
23672-07-3
Molecular Weight:
341.43
MDL number:
MFCD00055220
UNSPSC Code:
12352200
PubChem Substance ID:
24278709
NACRES:
NA.77

Assay

≥98% (titration)

mp

183-186 °C (lit.)

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

CCN1CCC[C@H]1CNC(=O)c2cc(ccc2OC)S(N)(=O)=O

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

InChI key

BGRJTUBHPOOWDU-NSHDSACASA-N

Gene Information

human ... DRD2(1813) , DRD3(1814)
rat ... Adra1a(29412) , Drd2(24318) , Drd3(29238) , Htr1a(24473) , Htr2a(29595)

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Application

(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

Biochem/physiol Actions

(S)-(−)-Sulpiride or Levosulpiride blocks the inhibitory enteric D2 receptors (neuronal and muscular). It has prokinetic activity and is effective in the treatment of functional dyspepsia and gastroparesis in insulin-dependent diabetes mellitus patients.7,8 Since dopamine controls human sexual function, (S)-(−)-Sulpiride is reportedly effective in treatment of erectile dysfunctions.9
D2 dopamine receptor antagonist; antipsychotic.

Features and Benefits

This compound was developed by Sanofi Aventis. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Takuya Hikima et al.
Cell reports, 35(1), 108951-108951 (2021-04-08)
Somatodendritic dopamine (DA) release from midbrain DA neurons activates D2 autoreceptors on these cells to regulate their activity. However, the source of autoregulatory DA remains controversial. Here, we test the hypothesis that D2 autoreceptors on a given DA neuron in
In Bok Paek et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 809(2), 345-350 (2004-08-19)
A rapid, sensitive and selective hydrophilic interaction liquid chromatography-tandem mass spectrometric (HILIC-MS/MS) method for the determination of levosulpiride in human plasma was developed. Levosulpiride and internal standard, tiapride were extracted from human plasma with ethyl acetate at pH 11 and
Trine Ljungstrom et al.
Pflugers Archiv : European journal of physiology, 446(6), 684-694 (2003-06-27)
Activation of KCNQ potassium channels by stimulation of co-expressed dopamine D(2) receptors was studied electrophysiologically in Xenopus laevis oocytes and in mammalian cells. To address the specificity of the interaction between D(2)-like receptors and KCNQ channels, combinations of KCNQ1-5 channels
W Hauber et al.
Behavioural brain research, 106(1-2), 143-150 (1999-12-14)
In the present study, the involvement of dopamine D1 and D2 receptors in the dorsal globus pallidus (GP) in motor control was investigated in rats. Results show that bilateral microinfusions of the dopamine D1 receptor antagonist SCH23390 or the dopamine
Hae-Won Shin et al.
Movement disorders : official journal of the Movement Disorder Society, 24(15), 2249-2253 (2009-10-02)
Levosulpiride is a substituted benzamide that is widely used for the management of dyspepsia and emesis. However, little is known about levosulpiride-induced movement disorders (LIM). The aim of this study was to investigate the clinical characteristics of patients with LIM.
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