Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H24N2O4S.ClH |
Molecular Weight | 364.888 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCN(CC)CCNC(=O)C1=C(OC)C=CC(=C1)S(C)(=O)=O
InChI
InChIKey=OTFDPNXIVHBTKW-UHFFFAOYSA-N
InChI=1S/C15H24N2O4S.ClH/c1-5-17(6-2)10-9-16-15(18)13-11-12(22(4,19)20)7-8-14(13)21-3;/h7-8,11H,5-6,9-10H2,1-4H3,(H,16,18);1H
DescriptionSources: http://db.cbg-meb.nl/Pars/h32520.pdfCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11520476
Sources: http://db.cbg-meb.nl/Pars/h32520.pdf
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11520476
Tiapride is a drug that selectively blocks D2 and D3 dopamine receptors in the brain. It is used to treat a variety of neurological and psychiatric disorders including dyskinesia, alcohol withdrawal syndrome, negative symptoms of psychosis, and agitation and aggression in the elderly. A derivative of benzamide, tiapride is chemically and functionally similar to other benzamide antipsychotics such as sulpiride and amisulpride known for their dopamine antagonist effects. Tiapride is marketed under various trade names and is widely available outside of the United States. The most common trade name for tiapride is Tiapridal, which is used throughout Europe, Russia, as well as parts of South America, the Middle East, and North Africa. It is also sold under different names in Italy (Italprid, Sereprile), Japan (Tialaread, Tiaryl, Tiaprim, Tiaprizal), Chile (Sereprid), Germany (Tiaprid, Tiapridex), and China (Tiapride).
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL339 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3761757 |
45.8 µM [IC50] | ||
Target ID: 1.01906672E8 Gene Symbol: DRD4 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3761757 |
11.7 µM [IC50] | ||
Target ID: CHEMBL234 |
180.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Tiacob Approved UseFor the treatment of neuroleptic-induced tardive dyskinesia, mainly oro-bucco-lingual type. Launch Date2005 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Tiapride. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in geriatric agitation. | 1993 Sep-Oct |
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Psychosis in children: diagnosis and treatment. | 2001 Jun |
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Flow-injection chemiluminometric analysis of some benzamides by their sensitizing effect on the cerium-sulphite reaction. | 2001 May 30 |
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Conventional and atypical antipsychotics in the elderly : a review. | 2003 |
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[Autonomic cardiovascular regulation in patients with tics and Tourette syndrome]. | 2005 |
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Weak inhibitors protect cholinesterases from stronger inhibitors (dichlorvos): in vitro effect of tiapride. | 2005 Mar-Apr |
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Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): in vitro effect of tiapride. | 2005 Nov-Dec |
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Tiapride pre-treatment in acute exposure to paraoxon: comparison of effects of administration at different points-in-time in rats. | 2006 Apr |
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Systematic review on the recurrence of postoperative nausea and vomiting after a first episode in the recovery room - implications for the treatment of PONV and related clinical trials. | 2006 Dec 13 |
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Efficacy and safety of outpatient alcohol detoxification with a combination of tiapride/carbamazepine: additional evidence. | 2006 Jan |
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Non-neuroleptic catecholaminergic drugs for neuroleptic-induced tardive dyskinesia. | 2006 Jan 25 |
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[Efficacy and adverse reactions of antipsychotics for neuropsychiatric symptoms in dementia: a systematic review]. | 2006 Jul 15 |
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[Identification of haloperidol and tiapride in the urine with thin layer chromatography]. | 2006 Mar-Apr |
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Simultaneous electrochemiluminescence determination of sulpiride and tiapride by capillary electrophoresis with cyclodextrin additives. | 2006 May 1 |
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Treatment of alcohol withdrawal syndrome with a combination of tiapride/carbamazepine: results of a pooled analysis in 540 patients. | 2006 Oct |
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Tourette's syndrome: clinical features, pathophysiology, and therapeutic approaches. | 2007 |
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Membrane sensors for the selective determination of tiapride in presence of its degradation products. | 2007 Aug |
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Impaired cognition and attention in adults: pharmacological management strategies. | 2007 Feb |
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[Carbamazepine intoxication. Complication of alcohol detoxification with combined carbamazepine and tiapride]. | 2007 Jan |
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[The analysis of tiapride in cadaveric material]. | 2007 Jan-Feb |
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Comparison of two pre-exposure treatment regimens in acute organophosphate (paraoxon) poisoning in rats: tiapride vs. pyridostigmine. | 2007 Mar |
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[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. | 2007 Mar |
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Anti-aggressive effects of GHB in OF.1 strain mice: involvement of dopamine D2 receptors. | 2007 Mar 30 |
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Stability-indicating methods for determination of tiapride in pure form, pharmaceutical preparation, and human plasma. | 2007 Nov-Dec |
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[Toxicological characteristic of neuroleptics--substituted benzamides]. | 2007 Nov-Dec |
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The efficacy of the dopamine D2/D3 antagonist tiapride in maintaining abstinence: a randomized, double-blind, placebo-controlled trial in 299 alcohol-dependent patients. | 2007 Oct |
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Metoclopramide protection of diazinon-induced toxicosis in chickens. | 2007 Sep |
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[Case of enzyme-linked immunoglobulin with persistent elevation of lactate dehydrogenase activity in serum by administration of an anti-psychotic drug]. | 2008 Aug |
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A thyrotoxicosis outbreak due to dietary pills in Paris. | 2008 Dec |
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Relationship between obesity and antipsychotic drug use in the adult population: a longitudinal, retrospective claim database study in Primary Care settings. | 2008 Feb |
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Successful treatment of tardive lingual dystonia with botulinum toxin: case report and review of the literature. | 2008 Jul 1 |
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Voluntary motor drive: possible reduction in Tourette syndrome. | 2008 Jun |
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[D3 agonism: an augmentative treatment in tardive dyskinesia? A case report]. | 2008 Nov |
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Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine. | 2009 |
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Aripiprazole in the pharmacotherapy of Gilles de la Tourette syndrome in adult patients. | 2009 |
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[Tiapride with the horn of saiga tatarica in the treatment of hemifacial spasm]. | 2009 Aug |
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Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study. | 2009 Dec |
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Liquid chromatography/tandem mass spectrometry for the determination of changrolin in rat plasma: application to a bioavailability study. | 2009 Sep 8 |
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Central adrenal insufficiency and diabetes insipidus misdiagnosed as severe depression. | 2010 |
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Medications acting on the dopaminergic system in the treatment of alcoholic patients. | 2010 |
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Classification of drugs based on properties of sodium channel inhibition: a comparative automated patch-clamp study. | 2010 Dec 20 |
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Pregabalin, tiapride and lorazepam in alcohol withdrawal syndrome: a multi-centre, randomized, single-blind comparison trial. | 2010 Feb |
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Depression, extrapyramidal symptoms, dementia and an unexpected outcome: a case report. | 2010 Feb 2 |
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[Observation on therapeutic effect of tic disorders treated with local acupuncture]. | 2010 Jun |
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[A control study of aripiprazole and tiapride treatment for tic disorders in children]. | 2010 Jun |
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Gene expression of NMDA receptor subunits in the cerebellum of elderly patients with schizophrenia. | 2010 Mar |
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[Application of near-infrared spectroscopy for differential detection of neuroleptics, derivatives of benzamides]. | 2010 May-Jun |
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Response of i(kr) and HERG currents to the antipsychotics tiapride and sulpiride. | 2010 Oct |
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Presynaptic dopaminergic agonists increased gripping-generated immobility episodes in the myelin-mutant taiep rat. | 2010 Oct 15 |
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Neuroleptic malignant syndrome induced by combination therapy with tetrabenazine and tiapride in a Japanese patient with Huntington's disease at the terminal stage of recurrent breast cancer. | 2014 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: http://db.cbg-meb.nl/mri/spc/nlh-0752-001.pdf
Adults should take 100 – 200 mg tiapride three times daily, depending on the severity of the disease and the body weight of the individual . The proposed daily dose for the claimed indication is 300 – 600 mg tiapride.
The effect of treatment may not be apparent until after a period of 4-6 weeks of treatment. Tiapride tablets should preferably be taken with a little liquid after meals.
Route of Administration:
Oral
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/21165329
Curator's Comment: Effects of tiapride on hERG channels expressed in Xenopus oocytes and also on delayed rectifier K(+) currents in guinea pig cardiomyocytes were studied.
Tiapride increased the potential for half-maximal activation (V(1/2)) of HERG at 10~300 uM. In guinea pig ventricular myocytes, bath applications of 100 and 500 uM tiapride at 36℃ blocked rapidly activating delayed rectifier K(+) current (I(Kr)) by 40.3% and 70.0%, respectively.
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256-908-4
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CHEMBL84158
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DTXSID4045210
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25N106WEDO
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100000091110
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51012-33-0
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m10846
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SUB04854MIG
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DBSALT002373
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ACTIVE MOIETY
SUBSTANCE RECORD