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S8010

(±)-Sulpiride

Name: (±)-Sulpiride
Brand: SIGMA

Synonym(s):

(±)-5-(Aminosulfonyl)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-2-methoxybenzamide, (±)-N-1-(Ethylpyrrolidin-2-ylmethyl)-2-methoxy-5-sulfamoylbenzamide

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About This Item

Empirical Formula (Hill Notation):

C₁₅H₂₃N₃O₄S

CAS Number:

15676-16-1

Molecular Weight:

341.43

EC Number:

239-753-7

MDL number:

MFCD00055061

UNSPSC Code:

12352200

PubChem Substance ID:

24277933

NACRES:

NA.77

form

powder

Quality Level

100

color

white

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 8.0 mg/mL
0.1 M HCl: soluble
H₂O: slightly soluble
ethanol: soluble

originator

Sanofi Aventis

storage temp.

2-8°C

SMILES string

CCN1CCCC1CNC(=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)

InChI key

BGRJTUBHPOOWDU-UHFFFAOYSA-N

Gene Information

human ... CA1(759) , CA2(760) , CA4(762) , CA5A(763) , CA5B(11238) , CA9(768) , DRD2(1813)

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Application

(±)-Sulpiride was used to study the effect of dopamine D₂ receptor signaling on calcium channels in rat pituitary melanotropic cells.⁴⁷

Biochem/physiol Actions

(±)-Sulpiride is a D₂ dopamine antagonist and an effective treatment for schizophrenia when used in combination with clozapine, a relatively weak D₂-dopaminergic antagonist. It is an antipsychotic agent and also exhibits neuroleptic properties but poorly penetrates the central nervous system.^45,46

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.

Reconstitution

Solutions may be stored for several days at 4 °C.

Pictograms

GHS08

Signal Word

Warning

Hazard Statements

H361

Precautionary Statements

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Repr. 2

WGK

WGK 2

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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Dopamine D2 receptor stimulation differentially affects voltage-activated calcium channels in rat pituitary melanotropic cells.

J A Keja et al.

The Journal of physiology, 450, 409-435 (1992-05-01)

1. Whole-cell voltage clamp recordings were made from 141 rat pituitary melanotropic cells in short-term, serum-free, primary culture. The effects of the dopamine D2 receptor agonist, LY 171555, on sodium, potassium and barium currents were investigated. 2. Application of 1

Sulpiride augmentation in people with schizophrenia partially responsive to clozapine. A double-blind, placebo-controlled study.

R Shiloh et al.

The British journal of psychiatry : the journal of mental science, 171, 569-573 (1998-03-31)

We hypothesised that a combined regimen of clozapine, a relatively weak D2-dopaminergic antagonist, and sulpiride, a selective D2 blocker, would demonstrate a greater antipsychotic efficacy by enhancing the D2 blockade of clozapine. Twenty-eight people with schizophrenia, previously unresponsive to typical

Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX.

Giuseppina De Simone et al.

Journal of medicinal chemistry, 49(18), 5544-5551 (2006-09-01)

An approach for designing bioreductive, hypoxia-activatable carbonic anhydrase (CA, EC 4.2.1.1) inhibitors targeting the tumor-associated isoforms is reported. Sulfonamides incorporating 3,3'-dithiodipropionamide/2,2'-dithiodibenzamido moieties were prepared and reduced enzymatically/chemically in conditions present in hypoxic tumors, leading to thiols. The X-ray crystal structure

Identifying clinically meaningful symptom response cut-off values on the SANS in predominant negative symptoms.

Stephen Z Levine et al.

Schizophrenia research, 145(1-3), 125-127 (2013-02-12)

The treatment and measurement of negative symptoms are currently at issue in schizophrenia, but the clinical meaning of symptom severity and change is unclear. To offer a clinically meaningful interpretation of severity and change scores on the Scale for the

Expanding Role of Dopaminergic Inhibition in Hypercapnic Responses of Cultured Rat Carotid Body Cells: Involvement of Type II Glial Cells.

Erin M Leonard et al.

International journal of molecular sciences, 21(15) (2020-08-06)

Dopamine (DA) is a well-studied neurochemical in the mammalian carotid body (CB), a chemosensory organ involved in O2 and CO2/H+ homeostasis. DA released from receptor (type I) cells during chemostimulation is predominantly inhibitory, acting via pre- and post-synaptic dopamine D2

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