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

Molecular Formula	C15H24N2O4S
Molecular Weight	328.427
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 311 Target ID: CHEMBL339 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3761757	Antagonist 2849	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 2849	11.7 µM [IC50]
Dopamine D3 receptor 97 Target ID: CHEMBL234 Sources: https://www.biotrend.com/file_fournisseur/c1b9_bg0338-coa.pdf	Antagonist 2849	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 8583	Tiacob Approved Use For the treatment of neuroleptic-induced tardive dyskinesia, mainly oro-bucco-lingual type. Launch Date 2005
Huntington's disease 28 Sources: http://www.promed.cz/en/prescription-drugs/tiaprid-pmcs-100-mg	Primary	Phase III 665	Unknown Approved Use Unknown
Tourette's syndrome 20 Sources: https://clinicaltrials.gov/ct2/show/NCT01501695	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
720 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=22	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.876 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=22	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
213.4 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_1190004F1161_1_007_1F.pdf#page=17	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.47 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2948825/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
5.89 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=22	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1332 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_1190004F1161_1_007_1F.pdf#page=17	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5.89 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2948825/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
3.91 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=22	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.91 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=22	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
21.6 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=23	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
8.63 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=23	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
7.54 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=23	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.24 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=23	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.5 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400813_1190004F1161_1_007_1F.pdf#page=17	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	TIAPRIDE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
229 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2948825/	100 mg 3 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered:	TIAPRIDE serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
90% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/4/530169_1190004C1025_4_016_1F.pdf#page=24			TIAPRIDE plasma	Homo sapiens
100% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2948825/			TIAPRIDE serum	Homo sapiens

Doses

Dose	Population	Adverse events
2.5 g single, oral Overdose Dose: 2.5 g Route: oral Route: single Dose: 2.5 g Sources: https://pubmed.ncbi.nlm.nih.gov/29135905/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/29135905/	Sources: https://pubmed.ncbi.nlm.nih.gov/29135905/
3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	Disc. AE: Extrapyramidal symptoms, Sedation... AEs leading to discontinuation/dose reduction: Extrapyramidal symptoms (12.5%) Sedation (12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/
3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	Disc. AE: Rigidity, Extrapyramidal symptoms... AEs leading to discontinuation/dose reduction: Rigidity (14.3%) Extrapyramidal symptoms (14.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/

AEs

AE	Significance	Dose	Population
Extrapyramidal symptoms	12.5% Disc. AE	3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/
Sedation	12.5% Disc. AE	3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/
Extrapyramidal symptoms	14.3% Disc. AE	3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/
Rigidity	14.3% Disc. AE	3 g 1 times / day multiple, oral Studied dose Dose: 3 g, 1 times / day Route: oral Route: multiple Dose: 3 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6241563/

PubMed

Title	Date	PubMed
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
Classification of drugs based on properties of sodium channel inhibition: a comparative automated patch-clamp study.	2010-12-20	21187965
Presynaptic dopaminergic agonists increased gripping-generated immobility episodes in the myelin-mutant taiep rat.	2010-10-15	20692320
Response of i(kr) and HERG currents to the antipsychotics tiapride and sulpiride.	2010-10	21165329
[Application of near-infrared spectroscopy for differential detection of neuroleptics, derivatives of benzamides].	2010-08-26	20734788
[Observation on therapeutic effect of tic disorders treated with local acupuncture].	2010-06	20578384
[A control study of aripiprazole and tiapride treatment for tic disorders in children].	2010-06	20540847
Gene expression of NMDA receptor subunits in the cerebellum of elderly patients with schizophrenia.	2010-03	19856012
Depression, extrapyramidal symptoms, dementia and an unexpected outcome: a case report.	2010-02-02	20181069
Pregabalin, tiapride and lorazepam in alcohol withdrawal syndrome: a multi-centre, randomized, single-blind comparison trial.	2010-02	20078487
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
Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study.	2009-12	19488984
Liquid chromatography/tandem mass spectrometry for the determination of changrolin in rat plasma: application to a bioavailability study.	2009-09-08	19467818
[Tiapride with the horn of saiga tatarica in the treatment of hemifacial spasm].	2009-08	20041610
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
A thyrotoxicosis outbreak due to dietary pills in Paris.	2008-12	19337445
[D3 agonism: an augmentative treatment in tardive dyskinesia? A case report].	2008-11	18504692
[Case of enzyme-linked immunoglobulin with persistent elevation of lactate dehydrogenase activity in serum by administration of an anti-psychotic drug].	2008-08	18800622
Successful treatment of tardive lingual dystonia with botulinum toxin: case report and review of the literature.	2008-07-01	17936461
Voluntary motor drive: possible reduction in Tourette syndrome.	2008-06	18196201
Relationship between obesity and antipsychotic drug use in the adult population: a longitudinal, retrospective claim database study in Primary Care settings.	2008-02	18728769
Stability-indicating methods for determination of tiapride in pure form, pharmaceutical preparation, and human plasma.	2008-01-16	18193732
[Toxicological characteristic of neuroleptics--substituted benzamides].	2007-12-28	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.	2007-10	17076934
Metoclopramide protection of diazinon-induced toxicosis in chickens.	2007-09	17679771
Membrane sensors for the selective determination of tiapride in presence of its degradation products.	2007-08	17666880
Anti-aggressive effects of GHB in OF.1 strain mice: involvement of dopamine D2 receptors.	2007-03-30	17050057
[The analysis of tiapride in cadaveric material].	2007-03-07	17338338
Comparison of two pre-exposure treatment regimens in acute organophosphate (paraoxon) poisoning in rats: tiapride vs. pyridostigmine.	2007-03	17056080
[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome].	2007-03	16924461
Impaired cognition and attention in adults: pharmacological management strategies.	2007-02	19300541
[Carbamazepine intoxication. Complication of alcohol detoxification with combined carbamazepine and tiapride].	2007-01	17186186
Tourette's syndrome: clinical features, pathophysiology, and therapeutic approaches.	2007	17726915
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.	2006-12-13	17166262
Treatment of alcohol withdrawal syndrome with a combination of tiapride/carbamazepine: results of a pooled analysis in 540 patients.	2006-10	16917685
[Efficacy and adverse reactions of antipsychotics for neuropsychiatric symptoms in dementia: a systematic review].	2006-07-15	16886695
[Identification of haloperidol and tiapride in the urine with thin layer chromatography].	2006-07-11	16826845
Simultaneous electrochemiluminescence determination of sulpiride and tiapride by capillary electrophoresis with cyclodextrin additives.	2006-05-01	16569516
Tiapride pre-treatment in acute exposure to paraoxon: comparison of effects of administration at different points-in-time in rats.	2006-04	16479322
Non-neuroleptic catecholaminergic drugs for neuroleptic-induced tardive dyskinesia.	2006-01-25	16437424
Efficacy and safety of outpatient alcohol detoxification with a combination of tiapride/carbamazepine: additional evidence.	2006-01	16453252
Weak inhibitors protect cholinesterases from strong inhibitors (paraoxon): in vitro effect of tiapride.	2005-09-30	16193528
Weak inhibitors protect cholinesterases from stronger inhibitors (dichlorvos): in vitro effect of tiapride.	2005-07-23	16036766
[Autonomic cardiovascular regulation in patients with tics and Tourette syndrome].	2005	16252383
Conventional and atypical antipsychotics in the elderly : a review.	2003	17535043
Psychosis in children: diagnosis and treatment.	2001-06	22033588
Flow-injection chemiluminometric analysis of some benzamides by their sensitizing effect on the cerium-sulphite reaction.	2001-05-30	18968294
Tiapride. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in geriatric agitation.	1993-09-01	8241609

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.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:59:15 GMT 2025` Edited by `admin` on `Wed Apr 02 08:59:15 GMT 2025`
Record UNII	LAH70H9JPH
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NSC-758225

Preferred Name

English

TIAPRIDE

Official Name

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