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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24N2O4S
Molecular Weight 328.4287
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIAPRIDE

SMILES

CCN(CC)CCN=C(c1cc(ccc1OC)S(=O)(=O)C)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 328.4287
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
45.8 µM [IC50]
Target ID: 1.01906672E8
Gene Symbol: DRD4
11.7 µM [IC50]
180.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Tiacob

Approved Use

For the treatment of neuroleptic-induced tardive dyskinesia, mainly oro-bucco-lingual type.

Launch Date

1.12008954E12
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Tiapride. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in geriatric agitation.
1993 Sep-Oct
Psychosis in children: diagnosis and treatment.
2001 Jun
Flow-injection chemiluminometric analysis of some benzamides by their sensitizing effect on the cerium-sulphite reaction.
2001 May 30
Influence of tiapride on platelet counts in healthy volunteers and patients with movement disorders.
2003 Jun
Successful therapy of tardive dyskinesia in a 71-year-old woman with a combination of tetrabenazine, olanzapine and tiapride.
2003 Mar
Direct determination of benzamides in serum by column-switching high-performance liquid chromatography.
2003 May
Tourette syndrome: efficient treatment with ziprasidone and normalization of body weight in a patient with excessive weight gain under tiapride.
2004 Aug
Early administration of tiapride to young rats without long-lasting changes in the development of the dopaminergic system.
2004 Jul
Hydrophilic interaction liquid chromatography-tandem mass spectrometry for the determination of levosulpiride in human plasma.
2004 Oct 5
Determination of tiapride in human plasma using hydrophilic interaction liquid chromatography-tandem mass spectrometry.
2004 Sep
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
[Iatrogenic neurological disorders in old people: a review].
2005 Jan
Tiapride pre-treatment in acute exposure to paraoxon: comparison of effects of administration at different points-in-time in rats.
2006 Apr
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
Efficacy and safety of outpatient alcohol detoxification with a combination of tiapride/carbamazepine: additional evidence.
2006 Jan
Non-neuroleptic catecholaminergic drugs for neuroleptic-induced tardive dyskinesia.
2006 Jan 25
[Efficacy and adverse reactions of antipsychotics for neuropsychiatric symptoms in dementia: a systematic review].
2006 Jul 15
[Identification of haloperidol and tiapride in the urine with thin layer chromatography].
2006 Mar-Apr
Simultaneous electrochemiluminescence determination of sulpiride and tiapride by capillary electrophoresis with cyclodextrin additives.
2006 May 1
Treatment of alcohol withdrawal syndrome with a combination of tiapride/carbamazepine: results of a pooled analysis in 540 patients.
2006 Oct
Impaired cognition and attention in adults: pharmacological management strategies.
2007 Feb
Comparison of two pre-exposure treatment regimens in acute organophosphate (paraoxon) poisoning in rats: tiapride vs. pyridostigmine.
2007 Mar
[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome].
2007 Mar
Anti-aggressive effects of GHB in OF.1 strain mice: involvement of dopamine D2 receptors.
2007 Mar 30
Stability-indicating methods for determination of tiapride in pure form, pharmaceutical preparation, and human plasma.
2007 Nov-Dec
[Toxicological characteristic of neuroleptics--substituted benzamides].
2007 Nov-Dec
Metoclopramide protection of diazinon-induced toxicosis in chickens.
2007 Sep
[Case of enzyme-linked immunoglobulin with persistent elevation of lactate dehydrogenase activity in serum by administration of an anti-psychotic drug].
2008 Aug
A thyrotoxicosis outbreak due to dietary pills in Paris.
2008 Dec
Relationship between obesity and antipsychotic drug use in the adult population: a longitudinal, retrospective claim database study in Primary Care settings.
2008 Feb
Successful treatment of tardive lingual dystonia with botulinum toxin: case report and review of the literature.
2008 Jul 1
Voluntary motor drive: possible reduction in Tourette syndrome.
2008 Jun
[D3 agonism: an augmentative treatment in tardive dyskinesia? A case report].
2008 Nov
Development of membrane selective electrode for determination of the antipsychotic sulpiride in pharmaceuticals and urine.
2009
Aripiprazole in the pharmacotherapy of Gilles de la Tourette syndrome in adult patients.
2009
[Tiapride with the horn of saiga tatarica in the treatment of hemifacial spasm].
2009 Aug
Rapid quantification of levosulpiride in human plasma using RP-HPLC-MS/MS for pharmacokinetic and bioequivalence study.
2009 Dec
Liquid chromatography/tandem mass spectrometry for the determination of changrolin in rat plasma: application to a bioavailability study.
2009 Sep 8
Central adrenal insufficiency and diabetes insipidus misdiagnosed as severe depression.
2010
Medications acting on the dopaminergic system in the treatment of alcoholic patients.
2010
Classification of drugs based on properties of sodium channel inhibition: a comparative automated patch-clamp study.
2010 Dec 20
Pregabalin, tiapride and lorazepam in alcohol withdrawal syndrome: a multi-centre, randomized, single-blind comparison trial.
2010 Feb
Depression, extrapyramidal symptoms, dementia and an unexpected outcome: a case report.
2010 Feb 2
[Observation on therapeutic effect of tic disorders treated with local acupuncture].
2010 Jun
[A control study of aripiprazole and tiapride treatment for tic disorders in children].
2010 Jun
Gene expression of NMDA receptor subunits in the cerebellum of elderly patients with schizophrenia.
2010 Mar
[Application of near-infrared spectroscopy for differential detection of neuroleptics, derivatives of benzamides].
2010 May-Jun
Response of i(kr) and HERG currents to the antipsychotics tiapride and sulpiride.
2010 Oct
Presynaptic dopaminergic agonists increased gripping-generated immobility episodes in the myelin-mutant taiep rat.
2010 Oct 15
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

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
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:59:31 UTC 2021
Edited
by admin
on Fri Jun 25 21:59:31 UTC 2021
Record UNII
LAH70H9JPH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIAPRIDE
INN   MI   WHO-DD  
INN  
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
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
FDA ORPHAN DRUG 111798
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
NCI_THESAURUS C66883
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
WHO-VATC QN05AL03
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C152602
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
INN
3289
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
EPA CompTox
51012-32-9
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
DRUG CENTRAL
2651
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
FDA UNII
LAH70H9JPH
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
EVMPD
SUB11010MIG
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
CAS
51012-32-9
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
DRUG BANK
DB13025
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
MERCK INDEX
M10846
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
TIAPRIDE
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
ChEMBL
CHEMBL84158
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
256-907-9
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
PUBCHEM
5467
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY
RXCUI
10588
Created by admin on Fri Jun 25 21:59:31 UTC 2021 , Edited by admin on Fri Jun 25 21:59:31 UTC 2021
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY