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Details

Stereochemistry ACHIRAL
Molecular Formula C15H24N2O4S.ClH
Molecular Weight 364.8896
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIAPRIDE HYDROCHLORIDE

SMILES

CCN(CC)CCN=C(c1cc(ccc1OC)S(=O)(=O)C)O.Cl

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

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Conventional and atypical antipsychotics in the elderly : a review.
2003
[Autonomic cardiovascular regulation in patients with tics and Tourette syndrome].
2005
Tiapride may accelerate lung cancer in older people: a case report.
2005 Apr
[Iatrogenic neurological disorders in old people: a review].
2005 Jan
Treatment of alcohol withdrawal syndrome with combined carbamazepine and tiapride in a patient with probable sleep apnoe syndrome.
2005 Mar
Weak inhibitors protect cholinesterases from stronger inhibitors (dichlorvos): in vitro effect of tiapride.
2005 Mar-Apr
Pheochromocytoma unmasked by amisulpride and tiapride.
2005 May
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
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
Tourette's syndrome: clinical features, pathophysiology, and therapeutic approaches.
2007
Membrane sensors for the selective determination of tiapride in presence of its degradation products.
2007 Aug
Impaired cognition and attention in adults: pharmacological management strategies.
2007 Feb
[Carbamazepine intoxication. Complication of alcohol detoxification with combined carbamazepine and tiapride].
2007 Jan
[The analysis of tiapride in cadaveric material].
2007 Jan-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
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
[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 21:07:26 UTC 2021
Edited
by admin
on Fri Jun 25 21:07:26 UTC 2021
Record UNII
25N106WEDO
Record Status Validated (UNII)
Record Version
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Name Type Language
TIAPRIDE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
SEREPRILE
Brand Name English
TIAPRIDE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
ITALPRID
Brand Name English
LUXOBEN
Brand Name English
TIAPRIDE HYDROCHLORIDE [WHO-DD]
Common 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
GRAMALIL
Brand Name English
TIAPRIDE HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
256-908-4
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
ChEMBL
CHEMBL84158
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
EPA CompTox
51012-33-0
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
FDA UNII
25N106WEDO
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
PUBCHEM
39855
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
CAS
51012-33-0
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
MERCK INDEX
M10846
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY Merck Index
EVMPD
SUB04854MIG
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
DRUG BANK
DBSALT002373
Created by admin on Fri Jun 25 21:07:26 UTC 2021 , Edited by admin on Fri Jun 25 21:07:26 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY