TIAPRIDE HYDROCHLORIDE

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

Structure Search

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

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
Psychosis in children: diagnosis and treatment.	2001 Jun	22033588
Flow-injection chemiluminometric analysis of some benzamides by their sensitizing effect on the cerium-sulphite reaction.	2001 May 30	18968294
Conventional and atypical antipsychotics in the elderly : a review.	2003	17535043
[Autonomic cardiovascular regulation in patients with tics and Tourette syndrome].	2005	16252383
Weak inhibitors protect cholinesterases from stronger inhibitors (dichlorvos): in vitro effect of tiapride.	2005 Mar-Apr	16036766
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
[Identification of haloperidol and tiapride in the urine with thin layer chromatography].	2006 Mar-Apr	16826845
Simultaneous electrochemiluminescence determination of sulpiride and tiapride by capillary electrophoresis with cyclodextrin additives.	2006 May 1	16569516
Treatment of alcohol withdrawal syndrome with a combination of tiapride/carbamazepine: results of a pooled analysis in 540 patients.	2006 Oct	16917685
Tourette's syndrome: clinical features, pathophysiology, and therapeutic approaches.	2007	17726915
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
[Carbamazepine intoxication. Complication of alcohol detoxification with combined carbamazepine and tiapride].	2007 Jan	17186186
[The analysis of tiapride in cadaveric material].	2007 Jan-Feb	17338338
Comparison of two pre-exposure treatment regimens in acute organophosphate (paraoxon) poisoning in rats: tiapride vs. pyridostigmine.	2007 Mar	17056080
[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome].	2007 Mar	16924461
Anti-aggressive effects of GHB in OF.1 strain mice: involvement of dopamine D2 receptors.	2007 Mar 30	17050057
Stability-indicating methods for determination of tiapride in pure form, pharmaceutical preparation, and human plasma.	2007 Nov-Dec	18193732
[Toxicological characteristic of neuroleptics--substituted benzamides].	2007 Nov-Dec	18159758
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	17076934
Metoclopramide protection of diazinon-induced toxicosis in chickens.	2007 Sep	17679771
[Case of enzyme-linked immunoglobulin with persistent elevation of lactate dehydrogenase activity in serum by administration of an anti-psychotic drug].	2008 Aug	18800622
A thyrotoxicosis outbreak due to dietary pills in Paris.	2008 Dec	19337445
Relationship between obesity and antipsychotic drug use in the adult population: a longitudinal, retrospective claim database study in Primary Care settings.	2008 Feb	18728769
Successful treatment of tardive lingual dystonia with botulinum toxin: case report and review of the literature.	2008 Jul 1	17936461
Voluntary motor drive: possible reduction in Tourette syndrome.	2008 Jun	18196201
[D3 agonism: an augmentative treatment in tardive dyskinesia? A case report].	2008 Nov	18504692
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
[Tiapride with the horn of saiga tatarica in the treatment of hemifacial spasm].	2009 Aug	20041610
Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study.	2009 Dec	19488984
Liquid chromatography/tandem mass spectrometry for the determination of changrolin in rat plasma: application to a bioavailability study.	2009 Sep 8	19467818
Central adrenal insufficiency and diabetes insipidus misdiagnosed as severe depression.	2010	21769255
Medications acting on the dopaminergic system in the treatment of alcoholic patients.	2010	20482513
Classification of drugs based on properties of sodium channel inhibition: a comparative automated patch-clamp study.	2010 Dec 20	21187965
Pregabalin, tiapride and lorazepam in alcohol withdrawal syndrome: a multi-centre, randomized, single-blind comparison trial.	2010 Feb	20078487
Depression, extrapyramidal symptoms, dementia and an unexpected outcome: a case report.	2010 Feb 2	20181069
[Observation on therapeutic effect of tic disorders treated with local acupuncture].	2010 Jun	20578384
[A control study of aripiprazole and tiapride treatment for tic disorders in children].	2010 Jun	20540847
Gene expression of NMDA receptor subunits in the cerebellum of elderly patients with schizophrenia.	2010 Mar	19856012
[Application of near-infrared spectroscopy for differential detection of neuroleptics, derivatives of benzamides].	2010 May-Jun	20734788
Response of i(kr) and HERG currents to the antipsychotics tiapride and sulpiride.	2010 Oct	21165329
Presynaptic dopaminergic agonists increased gripping-generated immobility episodes in the myelin-mutant taiep rat.	2010 Oct 15	20692320
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 HYDROCHLORIDE

Common Name

English

SEREPRILE

Brand Name

English

TIAPRIDE HYDROCHLORIDE [EP MONOGRAPH]

Common Name

English

ITALPRID

Brand Name

English

LUXOBEN

Brand Name

English

BENZAMIDE, N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-5-(METHYLSULFONYL)-, MONOHYDROCHLORIDE

Common Name

English

TIAPRIDAL

Brand Name

English

BENZAMIDE, N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-5-(METHYLSULFONYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

TIAPRIDE HYDROCHLORIDE [MART.]

Common Name

English

TIAPRIDE HCL

Common Name

English

TIAPRIDEX

Brand Name

English

TIAPRIDE HYDROCHLORIDE [JAN]

Common Name

English

GRAMALIL

Brand Name

English

TIAPRIDE HYDROCHLORIDE [MI]

Common Name

English

Tiapride hydrochloride [WHO-DD]

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

256-908-4