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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
Jong Sam Baik et al.
Movement disorders : official journal of the Movement Disorder Society, 23(5), 746-748 (2008-01-11)
We describe three patients who presented with 4 to 5 Hz tremors of the suprahyoid region of the neck. Two developed their tremors in association with levosulpiride treatment. When they opened their mouths, the neck tremors disappeared; no tongue tremors
M Tonini et al.
Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver, 35(4), 244-250 (2003-06-13)
The dopamine D2 receptor antagonist levosulpiride is a substituted benzamide derivative, whose gastrokinetic properties are exploited clinically for the management of functional dyspepsia. However, for other benzamide derivatives, such as cisapride and mosapride, agonism towards serotonin 5-HT4 receptors is considered
P Melga et al.
Diabetes care, 20(1), 55-58 (1997-01-01)
We evaluated the effect of chronic administration of levosulpiride, a prokinetic drug that is a selective antagonist for D2 dopamine receptors, on the glycemic control of IDDM subjects. The study was performed on 40 long-standing IDDM subjects with clinical signs
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
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