TIAPRIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H24N2O4S
Molecular Weight	328.427
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCNC(=O)C1=C(OC)C=CC(=C1)S(C)(=O)=O

InChI

InChIKey=JTVPZMFULRWINT-UHFFFAOYSA-N

InChI=1S/C15H24N2O4S/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)

HIDE SMILES / InChI

Description
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	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL339 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3761757	Antagonist 2778	45.8 µM [IC50]
dopamine receptor D4 2 Target ID: 1.01906672E8 Gene Symbol: DRD4 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3761757	Antagonist 2778	11.7 µM [IC50]
Dopamine D3 receptor 91 Target ID: CHEMBL234 Sources: https://www.biotrend.com/file_fournisseur/c1b9_bg0338-coa.pdf	Antagonist 2778	180.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Tardive dyskinesia 15 Sources: http://db.cbg-meb.nl/mri/spc/nlh-0752-001.pdf	Primary	Approved 8429	Tiacob Approved Use For the treatment of neuroleptic-induced tardive dyskinesia, mainly oro-bucco-lingual type. Launch Date 2005
Huntington's disease 24 Sources: http://www.promed.cz/en/prescription-drugs/tiaprid-pmcs-100-mg	Primary	Phase III 656	Unknown Approved Use Unknown
Tourette's syndrome 20 Sources: https://clinicaltrials.gov/ct2/show/NCT01501695	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Tiapride. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in geriatric agitation.	1993 Sep-Oct	8241609
Clinical management of agitation in the elderly with tiapride.	2001 Jan	11520478
The preclinical pharmacologic profile of tiapride.	2001 Jan	11520476
Tiapride in gerontopsychiatry.	2001 Jan	11520473
Psychosis in children: diagnosis and treatment.	2001 Jun	22033588
Influence of the dopamine D2 receptor (DRD2) exon 8 genotype on efficacy of tiapride and clinical outcome of alcohol withdrawal.	2001 Nov	11692072
[Models of drug treatment in the attention deficit disorder with hyperactivity].	2002 Feb	12447798
A combination of carbamazepine/tiapride in outpatient alcohol detoxification. Results from an open clinical study.	2002 Oct	12451459
Conventional and atypical antipsychotics in the elderly : a review.	2003	17535043
Successful therapy of tardive dyskinesia in a 71-year-old woman with a combination of tetrabenazine, olanzapine and tiapride.	2003 Mar	12661802
Direct determination of benzamides in serum by column-switching high-performance liquid chromatography.	2003 May	12769385
Early administration of tiapride to young rats without long-lasting changes in the development of the dopaminergic system.	2004 Jul	15467972
Hydrophilic interaction liquid chromatography-tandem mass spectrometry for the determination of levosulpiride in human plasma.	2004 Oct 5	15315786
Determination of tiapride in human plasma using hydrophilic interaction liquid chromatography-tandem mass spectrometry.	2004 Sep	15473657
[Autonomic cardiovascular regulation in patients with tics and Tourette syndrome].	2005	16252383
Tiapride may accelerate lung cancer in older people: a case report.	2005 Apr	15817029
A randomized, observer-blind, controlled trial of the traditional Chinese medicine Yi-Gan San for improvement of behavioral and psychological symptoms and activities of daily living in dementia patients.	2005 Feb	15705012
Protective drugs in acute large-dose exposure to organophosphates: a comparison of metoclopramide and tiapride with pralidoxime in rats.	2005 Feb	15673862
[Iatrogenic neurological disorders in old people: a review].	2005 Jan	15732350
Treatment of alcohol withdrawal syndrome with combined carbamazepine and tiapride in a patient with probable sleep apnoe syndrome.	2005 Mar	15744634
Weak inhibitors protect cholinesterases from stronger inhibitors (dichlorvos): in vitro effect of tiapride.	2005 Mar-Apr	16036766
Pheochromocytoma unmasked by amisulpride and tiapride.	2005 May	15811908
Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): in vitro effect of tiapride.	2005 Nov-Dec	16193528
Tiapride pre-treatment in acute exposure to paraoxon: comparison of effects of administration at different points-in-time in rats.	2006 Apr	16479322
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	17166262
Efficacy and safety of outpatient alcohol detoxification with a combination of tiapride/carbamazepine: additional evidence.	2006 Jan	16453252
Non-neuroleptic catecholaminergic drugs for neuroleptic-induced tardive dyskinesia.	2006 Jan 25	16437424
[Efficacy and adverse reactions of antipsychotics for neuropsychiatric symptoms in dementia: a systematic review].	2006 Jul 15	16886695
Membrane sensors for the selective determination of tiapride in presence of its degradation products.	2007 Aug	17666880
Impaired cognition and attention in adults: pharmacological management strategies.	2007 Feb	19300541
[The analysis of tiapride in cadaveric material].	2007 Jan-Feb	17338338
[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome].	2007 Mar	16924461
A thyrotoxicosis outbreak due to dietary pills in Paris.	2008 Dec	19337445
Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine.	2009	22408528
Aripiprazole in the pharmacotherapy of Gilles de la Tourette syndrome in adult patients.	2009	18843565
Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study.	2009 Dec	19488984
Medications acting on the dopaminergic system in the treatment of alcoholic patients.	2010	20482513
[Observation on therapeutic effect of tic disorders treated with local acupuncture].	2010 Jun	20578384
[Application of near-infrared spectroscopy for differential detection of neuroleptics, derivatives of benzamides].	2010 May-Jun	20734788
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	24881749

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

TIAPRIDE

Official Name

English

NSC-758225

Code

English

TIAPRIDE [MI]

Common Name

English

N-(2-(DIETHYLAMINO)ETHYL)-5-(METHYLSULFONYL)-O-ANISAMIDE

Common Name

English

Tiapride [WHO-DD]

Common Name

English

tiapride [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05AL03