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Merck

S7771

(S)-(−)-Sulpiride

≥98% (titration)

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C15H23N3O4S
Número CAS:
23672-07-3
Peso molecular:
341.43
NACRES:
NA.77
PubChem Substance ID:
24278709
UNSPSC Code:
12352200
MDL number:
MFCD00055220
Assay:
≥98% (titration)
Quality level:
100

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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

SMILES string

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

InChI key

BGRJTUBHPOOWDU-NSHDSACASA-N

assay

≥98% (titration)

mp

183-186 °C (lit.)

originator

Sanofi Aventis

storage temp.

2-8°C

Quality Level

100

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
BCCG1240
BCCG0931
BCCB8318
BCBW2143
BCBW2144

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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
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
C Mansi et al.
Alimentary pharmacology & therapeutics, 14(5), 561-569 (2000-05-03)
The efficacy of several prokinetic drugs on dyspeptic symptoms and on gastric emptying rates are well-established in patients with functional dyspepsia, but formal studies comparing different prokinetic drugs are lacking. To compare the effects of chronic oral administration of cisapride
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
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