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S8010 Sigma

(±)-Sulpiride

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

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Properties

Related Categories Antagonists, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents,
form   powder
color   white
solubility   45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble8.0 mg/mL
  0.1 M HCl: soluble
  H2O: slightly soluble
  ethanol: soluble
originator   Sanofi Aventis
storage temp.   2-8°C
Gene Information   human ... CA1(759), CA2(760), CA4(762), CA5A(763), CA5B(11238), CA9(768), DRD2(1813)

Description

Reconstitution

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

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 is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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

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LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

WGK Germany 
2

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles

Peer-Reviewed Papers

References

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Sulpiride augmentation in people with schizophrenia partially responsive to clozapine. A double-blind, placebo-controlled study. Shiloh R, Zemishlany Z, Aizenberg D, et al. Br. J. Psychiatry 171, 569-73, (1997)

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Dopamine D2 receptor stimulation differentially affects voltage-activated calcium channels in rat pituitary melanotropic cells. Keja JA, Stoof JC, and Kits KS J. Physiol. 450, 409-35, (1992)

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Dopamine D1 or D2 receptor blockade in the globus pallidus produces akinesia in the rat. Hauber, W., and Lutz, S. Behav. Brain Res. 106, 143-150, (1999)

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Long-term treatment with antidepressants increases glucocorticoid receptor binding and gene expression in cultured rat hippocampal neurones. Okugawa, G., et al. J. Neuroendocrinol. 11, 887-895, (1999)

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Diagnostic exercise. Lucke VM and Migaki G Lab. Anim. Sci. 29(5), 601-2, (1979)

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Cortically driven Fos induction in the striatum is amplified by local dopamine D2-class receptor blockade. Eur. Berretta, S., et al. Eur. J. Neurosci. 11, 4309-4319, (1999)

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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The relation between symptom improvement and gastric emptying in the treatment of diabetic and idiopathic gastroparesis. Janssen P, Harris MS, Jones M, et al. Am. J. Gastroenterol. 108(9), 1382-91, (2013)

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Exploring the role of different drug transport routes in permeability screening. Pär Matsson et al J. Med. Chem. 48, 604-13, (2005)

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Cloning, characterization, and inhibition studies of a beta-carbonic anhydrase from Brucella suis. Pascale Joseph et al J. Med. Chem. 53, 2277-85, (2010)

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Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c. Fabrizio Carta et al Bioorg. Med. Chem. Lett. 19, 6649-54, (2009)

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Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX. Giuseppina De Simone et al J. Med. Chem. 49, 5544-51, (2006)

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Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. Tomoko Minakuchi et al J. Med. Chem. 52, 2226-32, (2009)

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Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. Isao Nishimori et al J. Med. Chem. 52, 3116-20, (2009)

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A new ?-carbonic anhydrase from Brucella suis, its cloning, characterization, and inhibition with sulfonamides and sulfamates, leading to impaired pathogen growth. Pascale Joseph et al Bioorg. Med. Chem. 19, 1172-8, (2011)

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Identifying clinically meaningful symptom response cut-off values on the SANS in predominant negative symptoms. Levine SZ and Leucht S Schizophr. Res. 145(1-3), 125-7, (2013)

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Physicochemical determinants of human renal clearance. Manthena V S Varma et al J. Med. Chem. 52, 4844-52, (2009)

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Physicochemical space for optimum oral bioavailability: contribution of human intestinal absorption and first-pass elimination. Manthena V S Varma et al J. Med. Chem. 53, 1098-108, (2010)

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Carbonic anhydrase inhibitors. The mitochondrial isozyme VB as a new target for sulfonamide and sulfamate inhibitors. Isao Nishimori et al J. Med. Chem. 48, 7860-6, (2005)

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Carbonic anhydrase inhibitors: DNA cloning and inhibition studies of the alpha-carbonic anhydrase from Helicobacter pylori, a new target for developing sulfonamide and sulfamate gastric drugs. Isao Nishimori et al J. Med. Chem. 49, 2117-26, (2006)

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[Sulpiride: the best known atypical, safe neuroleptic drug. Review of literature]. Rzewuska M Psychiatr. Pol. 32(5), 655-66, (1998)

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[Metoclopramide, sulpiride, and chlorpromazine loading test]. Azuma K, Irahara M, and Aono T Nihon Rinsho. 55 Suppl 2, 249-51, (1997)

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[Sulpiride: an atypical neuroleptic with a wide spectrum of therapeutic claims]. Wasieczko A and Wasieczko Z Psychiatr. Pol. 30(6), 1009-16, (1996)

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[Effect of antipsychotic amisulpride on immune reactivity]. Idova GV, Al'perina EL, Lobacheva OA, et al. Eksp. Klin. Farmakol. 76(5), 14-7, (2013)

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Delusional infestation: a clinical profile. Bhatia MS, Jhanjee A, and Srivastava S Asian J. Psychiatr. 6(2), 124-7, (2013)

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[A case of male infertility caused by drug-induced hyperprolactinemia]. Takeshima T, Kuroda S, Kobayashi M, et al. Hinyokika Kiyo. 59(1), 65-7, (2013)

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[Effect of storax on concentration of sulpiride in brain and blood by MD-HPLC]. Liu P, Yu SS, and He XR Zhongguo Zhong Yao Za Zhi 37(21), 3307-11, (2012)

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Poisoning: fact or fiction? Flanagan RJ Med. Leg. J. 80(Pt 4), 127-48, (2012)

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[The comparative study on the efficacy of the combination of serotonin reuptake inhibitor antidepressants and antipsychotics in the treatment of recurrent depressive disorders]. D'iakonov AL and Lobanova IV Zh. Nevrol. Psikhiatr. Im. S. S. Korsakova 112(11 Pt 2), 61-6, (2012)

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Successful treatment of atypical depression with amisulpride: a case report. Agarwal SM, Rao NP, Venkatasubramanian G, et al. Asian J. Psychiatr. 5(4), 362, (2012)

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[Cardiac, respiratory, and motor activity in norm and after activation of catecholaminergic systems in newborn rat pups]. Kuznetsov SV, Dmitrieva LE, and Sizonov VA Zh. Evol. Biokhim. Fiziol. 48(4), 367-79, (2012)

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[Antiemetic properties of levo-sulpiride]. Guslandi M Minerva Med. 81(12), 855-60, (1990)

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Hypolipidemic and weight reducing activity of the ethanolic extract of Tamarindus indica fruit pulp in cafeteria diet- and sulpiride-induced obese rats. Vaneeta Jindal et al J. Pharmacol. Pharmacother. 2, 80-4, (2011)

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[Toxicity of sulpiride]. Ciszowski K, Szpak D, and Wilimowska J Prz. Lek. 67(8), 606-9, (2010)

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[Changes in the endocrine system in the course of sulpiride therapy]. Roś LT Pol. Merkur. Lekarski 11(66), 532-4, (2001)

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Sulpiride for schizophrenia. Soares BG, Fenton M, and Chue P Cochrane Database Syst. Rev. (2), CD001162, (2000)

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Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. Isao Nishimori et al J. Med. Chem. 50, 381-8, (2007)

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Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Isao Nishimori et al Bioorg. Med. Chem. 15, 7229-36, (2007)

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The Japanese toxicogenomics project: application of toxicogenomics. Takeki Uehara et al Mol. Nutr. Food. Res. 54, 218-27, (2010)

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Carbonic anhydrase inhibitors: inhibition of the beta-class enzyme from the yeast Saccharomyces cerevisiae with sulfonamides and sulfamates. Semra Isik et al Bioorg. Med. Chem. 17, 1158-63, (2009)

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The pharmacology of sulpiride--a dopamine receptor antagonist. O'Connor SE and Brown RA Gen. Pharmacol. 13(3), 185-93, (1982)

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Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides. Alessio Innocenti et al Bioorg. Med. Chem. 17, 4503-9, (2009)

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Calculating virtual log P in the alkane/water system (log P(N)(alk)) and its derived parameters deltalog P(N)(oct-alk) and log D(pH)(alk). Giulia Caron et al J. Med. Chem. 48, 3269-79, (2005)

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Inhibition studies of the ?-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates. Isao Nishimori et al Bioorg. Med. Chem. 19, 5023-30, (2011)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Attaining and sustaining remission of predominant negative symptoms. Levine SZ and Leucht S Schizophr. Res. 143(1), 60-4, (2013)

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Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. Mika Hilvo et al J. Med. Chem. 52, 646-54, (2009)

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Identification of new functional inhibitors of acid sphingomyelinase using a structure-property-activity relation model. Johannes Kornhuber et al J. Med. Chem. 51, 219-37, (2008)

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Spectroscopic investigation on the inclusion complex formation between amisulpride and γ-cyclodextrin. Negi JS and Singh S Carbohydr. Polym. 92(2), 1835-43, (2013)

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A risk-benefit assessment of sulpiride in the treatment of schizophrenia. Mauri MC, Bravin S, Bitetto A, et al. Drug Saf. 14(5), 288-98, (1996)

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N-(3-Fluoro-4-(4-(2-methoxy or 2,3-dichlorophenyl)piperazine-1-yl)butyl)arylcarboxamides as Selective Dopamine D3 Receptor Ligands: Critical Role of the Carboxamide Linker for D3 Receptor Selectivity Banala, A. K.; et al. J. Med. Chem. 54, 3581, (2011)

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Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs? Daniela Vullo et al Bioorg. Med. Chem. Lett. 15, 963-9, (2005)

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Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Anthony Bertucci et al Bioorg. Med. Chem. 17, 5054-8, (2009)

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Carbonic anhydrase inhibitors: the beta-carbonic anhydrase from Helicobacter pylori is a new target for sulfonamide and sulfamate inhibitors. Isao Nishimori et al Bioorg. Med. Chem. Lett. 17, 3585-94, (2007)

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Mismatch negativity and cognitive performance for the prediction of psychosis in subjects with at-risk mental state. Higuchi Y, Sumiyoshi T, Seo T, et al. PLoS ONE 8(1), e54080, (2013)

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Dopamine modulates persistent synaptic activity and enhances the signal-to-noise ratio in the prefrontal cortex. Kroener S, Chandler LJ, Phillips PE, et al. PLoS ONE 4(8), e6507, (2009)

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Prediction of drug intestinal absorption by new linear and non-linear QSPR. Alan Talevi et al Eur. J. Med. Chem. 46, 218-28, (2011)

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Modeling the similarity and divergence of dopamine D2-like receptors and identification of validated ligand-receptor complexes. Frank Boeckler et al J. Med. Chem. 48, 694-709, (2005)

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Preparation and pharmacological characterization of trans-2-amino-5(6)-fluoro-6(5)-hydroxy-1-phenyl-2,3-dihydro-1H-indenes as D2-like dopamine receptor agonists. Antonio Di Stefano et al J. Med. Chem. 48, 2646-54, (2005)

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Antagonism by haloperidol and its metabolites of mechanical hypersensitivity induced by intraplantar capsaicin in mice: role of sigma-1 receptors. José M. Entrena et al Psychopharmacology 205, 21-33, (2009)

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Carbonic anhydrase inhibitors. Inhibition studies with anions and sulfonamides of a new cytosolic enzyme from the scleractinian coral Stylophora pistillata. Anthony Bertucci et al Bioorg. Med. Chem. Lett. 21, 710-4, (2011)

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Ethanol-mediated facilitation of AMPA receptor function in the dorsomedial striatum: implications for alcohol drinking behavior. Wang J, Ben Hamida S, Darcq E, et al. J. Neurosci. 32(43), 15124-32, (2012)

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Sulpiride: an antipsychotic with selective dopaminergic antagonist properties. Caley CF and Weber SS Ann. Pharmacother. 29(2), 152-60, (1995)

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Methamphetamine-induced disruption of frontostriatal reward learning signals: relation to psychotic symptoms. Bernacer J, Corlett PR, Ramachandra P, et al. Am. J. Psychiatry 170(11), 1326-34, (2013)

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The mode of action of sulpiride as an atypical antidepressant agent. Jenner P and Marsden CD Adv. Biochem. Psychopharmacol. 32, 85-103, (1982)

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Carbonic anhydrase inhibitors: inhibition of cytosolic/tumor-associated isoforms I, II, and IX with iminodiacetic carboxylates/hydroxamates also incorporating benzenesulfonamide moieties. M Amelia Santos et al Bioorg. Med. Chem. Lett. 17, 1538-43, (2007)

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Augmentation with sulpiride for a schizophrenic patient partially responsive to clozapine. Stubbs JH, Haw CM, Staley CJ, et al. Acta Psychiatr. Scand. 102(5), 390-3; discussion 393-4, (2000)

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Light-dependent translocation of arrestin in rod photoreceptors is signaled through a phospholipase C cascade and requires ATP. Orisme W Cell. Signal. 22(3), 447-56, (2010)

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I.V. APD421 (amisulpride) prevents postoperative nausea and vomiting: a randomized, double-blind, placebo-controlled, multicentre trial. Kranke P, Eberhart L, Motsch J, et al. Br. J. Anaesth. 111(6), 938-45, (2013)

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Computational modeling of novel inhibitors targeting the Akt pleckstrin homology domain. Lei Du-Cuny et al Bioorg. Med. Chem. 17, 6983-92, (2009)

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Pharmacological assessment of methamphetamine-induced behavioral hyperactivity mediated by dopaminergic transmission in planarian Dugesia japonica. Tashiro N, Nishimura K, Daido K, et al. Biochem. Biophys. Res. Commun. 449(4), 412-8, (2014)

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Cloning, characterization and sulfonamide inhibition studies of an ?-carbonic anhydrase from the living fossil sponge Astrosclera willeyana. Anna Ohradanova et al Bioorg. Med. Chem. 20, 1403-10, (2012)

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Sulpiride augmentation for schizophrenia. Wang J, Omori IM, Fenton M, et al. Cochrane Database Syst. Rev. (1), CD008125, (2010)

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Experimental solubility profiling of marketed CNS drugs, exploring solubility limit of CNS discovery candidate. Yun W Alelyunas et al Bioorg. Med. Chem. Lett. 20, 7312-6, (2010)

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Carbonic anhydrase inhibitors: cloning and sulfonamide inhibition studies of a carboxyterminal truncated alpha-carbonic anhydrase from Helicobacter pylori. Isao Nishimori et al Bioorg. Med. Chem. Lett. 16, 2182-8, (2006)

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Neural computational prediction of oral drug absorption based on CODES 2D descriptors. A Guerra et al Eur. J. Med. Chem. 45, 930-40, (2010)

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Sulpiride versus placebo for schizophrenia. Omori IM and Wang J Cochrane Database Syst. Rev. (2), CD007811, (2009)

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Changes on D2-like receptor induced Gi protein activation and hippocampal dopamine release in kindled rats. Alcantara-Gonzalez D, Floran B, Escartin E, et al. Prog. Neuropsychopharmacol. Biol. Psychiatry 40, 246-51, (2013)

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QSAR-based permeability model for drug-like compounds. Rafael Gozalbes et al Bioorg. Med. Chem. 19, 2615-24, (2011)

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Antidepressant-like activity of ellagic acid in unstressed and acute immobilization-induced stressed mice. Dhingra D and Chhillar R Pharmacol. Rep. 64(4), 796-807, (2012)

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Sulpiride augmentation for schizophrenia. Wang J, Omori IM, Fenton M, et al. Schizophr. Bull. 36(2), 229-30, (2010)

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Prediction of volume of distribution values in human using immobilized artificial membrane partitioning coefficients, the fraction of compound ionized and plasma protein binding data. Xiaofan Sui et al Eur. J. Med. Chem. 44, 4455-60, (2009)

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Punishment-induced behavioral and neurophysiological variability reveals dopamine-dependent selection of kinematic movement parameters. Galea JM, Ruge D, Buijink A, et al. J. Neurosci. 33(9), 3981-8, (2013)

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Intrahippocampal administration of D2 but not D1 dopamine receptor antagonist suppresses the expression of conditioned place preference induced by morphine in the ventral tegmental area. Haghparast A, Esmaeili MH, Taslimi Z, et al. Neurosci. Lett. 541, 138-43, (2013)

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Possible mechanism of antidepressant effect of L-sulpiride. Serra G, Forgione A, D'Aquila PS, et al. Clin. Neuropharmacol. 13 Suppl 1, S76-83, (1990)

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Cognitive effects of a single dose of atypical antipsychotics in healthy volunteers compared with placebo or haloperidol. Chung YC, Park TW, Yang JC, et al. J. Clin. Psychopharmacol. 32(6), 778-86, (2012)

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Antipsychotic combination using low-dose antipsychotics is as efficacious and safe as, but cheaper, than optimal-dose monotherapy in the treatment of schizophrenia: a randomized, double-blind study. Lin CH, Wang FC, Lin SC, et al. Int. Clin. Psychopharmacol. 28(5), 267-74, (2013)

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Development of an in silico model for human skin permeation based on a Franz cell skin permeability assay. Pil H Lee et al Bioorg. Med. Chem. Lett. 20, 69-73, (2010)

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The effect of cholestasis on rewarding and exploratory behaviors induced by opioidergic and dopaminergic agents in mice. Ebrahimi-ghiri M, Nasehi M, Rostami P, et al. Arch. Iran. Med. 15(10), 617-24, (2012)

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[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. Müller-Vahl KR Nervenarzt 78(3), 264, 266-8, 270-1, (2007)

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Citalopram and levosulpiride: a dangerous drug combination for QT prolongation. Agosti S, Casalino L, Bertero G, et al. Am. J. Emerg. Med. 31(11), 1624.e1-2, (2013)

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[Schizophrenia-like psychotic symptoms in a patient with confirmed Huntington's disease: a case report]. Grabski B, Siwek M, Dudek D, et al. Psychiatr. Pol. 46(4), 665-75, (2012)

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Involvement of dopaminergic receptors of the rat nucleus accumbens in decreasing the conditioned place preference induced by lateral hypothalamus stimulation. Haghparast A, Omranifard A, Arezoomandan R, et al. Neurosci. Lett. 556, 10-4, (2013)

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A 6-week, randomized, multicentre, open-label study comparing efficacy and tolerability of amisulpride at a starting dose of 400 mg/day versus 800 mg/day in patients with acute exacerbations of schizophrenia. Lee SJ, Lee JH, Jung SW, et al. Clin. Drug Investig. 32(11), 735-45, (2012)

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Safety of the electroconvulsive therapy and amisulpride combination. Takács R, Iványi Z, Ungvari GS, et al. Psychiatr. Danub. 25(1), 76-9, (2013)

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Validated spectrofluorimetric method for determination of sulpiride in commercial formulations using Hantzsch condensation reaction. Shah J, Jan MR, Khan MN, et al. Pak. J. Pharm. Sci. 26(5), 921-8, (2013)

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[Possibilities in using sulpiride in the treatment of psychotic disorders]. Danilov DS Zh. Nevrol. Psikhiatr. Im. S. S. Korsakova 112(6), 91-7, (2012)

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Improvements in micturition and urinary retention after switching from amisulpiride to paliperidone in a schizophrenic patient. Lai CH J. Neuropsychiatry Clin. Neurosci. 24(4), E11-2, (2012)

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Anaphylaxis due to sulpiride and sensitization to metamizole. Alvarado MI, Cámara C, and Trabado A J. Investig. Allergol. Clin. Immunol. 22(5), 379-80, (2012)

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Charles Bonnet syndrome responding to amisulpride. Bhatia MS, Srivastava S, and Jhanjee A J. Neuropsychiatry Clin. Neurosci. 24(3), E40, (2012)

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