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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 of TIAPRIDE HYDROCHLORIDE

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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C15H24N2O4S
Molecular Weight 328.427
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).

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 45.8 µM [IC50]
dopamine receptor D4
2
Target ID: 1.01906672E8
Gene Symbol: DRD4
Antagonist
2778
 11.7 µM [IC50]
Antagonist
2778
 180.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Tiacob

Approved Use

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

Launch Date

1.12008954E12
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase III
656
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pharmacological options for the treatment of Tourette's disorder.
2001
Treatment of alcohol withdrawal: tiapride and carbamazepine versus clomethiazole. A pilot study.
2001 Aug
Influence of the dopamine D2 receptor (DRD2) exon 8 genotype on efficacy of tiapride and clinical outcome of alcohol withdrawal.
2001 Nov
Successful therapy of tardive dyskinesia in a 71-year-old woman with a combination of tetrabenazine, olanzapine and tiapride.
2003 Mar
Early administration of tiapride to young rats without long-lasting changes in the development of the dopaminergic system.
2004 Jul
[Identification of haloperidol and tiapride in the urine with thin layer chromatography].
2006 Mar-Apr
Tourette's syndrome: clinical features, pathophysiology, and therapeutic approaches.
2007
[Carbamazepine intoxication. Complication of alcohol detoxification with combined carbamazepine and tiapride].
2007 Jan
Comparison of two pre-exposure treatment regimens in acute organophosphate (paraoxon) poisoning in rats: tiapride vs. pyridostigmine.
2007 Mar
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
Depression, extrapyramidal symptoms, dementia and an unexpected outcome: a case report.
2010 Feb 2
[Application of near-infrared spectroscopy for differential detection of neuroleptics, derivatives of benzamides].
2010 May-Jun
Patents

Patents

06861072
2
JP2001523241A
2
JPH08512055A
14

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
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 Dec 15 19:25:37 UTC 2023
Edited
by admin
on Fri Dec 15 19:25:37 UTC 2023
Record UNII
25N106WEDO
Record Status Validated (UNII)
Record Version
  • Download
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
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
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL84158
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID4045210
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
FDA UNII
25N106WEDO
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
SMS_ID
100000091110
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
PUBCHEM
39855
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
CAS
51012-33-0
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
MERCK INDEX
m10846
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY Merck Index
EVMPD
SUB04854MIG
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
DRUG BANK
DBSALT002373
Created by admin on Fri Dec 15 19:25:37 UTC 2023 , Edited by admin on Fri Dec 15 19:25:37 UTC 2023
PRIMARY
Related Record Type Details
Structure of TIAPRIDE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BENZAMIDE, N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-5-(METHYLSULFONYL)-, N-OXIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of METHYL 5-MESYL-O-ANISATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N,N-DIETHYLETHYLENEDIAMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
Structure of 5-MESYL-O-ANISIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of TIAPRIDE
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