Identification
- Summary
Tiapride is a dopamine D2 and D3 receptor antagonist indicated in the treatment of chorea in Huntington's disease, as well as agitation and anxiety in the elderly or with acute or chronic alcoholism.
- Generic Name
- Tiapride
- DrugBank Accession Number
- DB13025
- Background
Tiapride is a selective D2 and D3 dopamine receptor blocker in the brain.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Tiapride (DB13025)
- Weight
- Average: 328.427
Monoisotopic: 328.145677956 - Chemical Formula
- C15H24N2O4S
- Synonyms
- Thiapride
- Tiaprida
- Tiapride
- Tiapridum
- External IDs
- FLO 1347
Pharmacology
- Indication
Tiapride is indicated for the treatment of a variety of neurological and psychiatric disorders including dyskinesia, alcohol withdrawal syndrome, negative symptoms of psychosis, and agitation and aggression in the elderly.
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- Contraindications & Blackbox Warnings
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Tiapride has a high degree of regional selectivity for limbic areas. One study found that tiapride shows over three times as much affinity for limbic areas than striatal areas as opposed to the near equal selectivity for limbic and striatal regions shown by haloperidol. Another study in rats found tiapride's affinity for the septum, a limbic region, to be over thirty times as high as for the striatum. Efficacy at the D2 receptor is moderate, with 80 percent of receptors occupied even in the presence of excess tiapride concentrations.
- Mechanism of action
Tiapride is a selective dopamine D2 and D3 receptor antagonist, offering an advantage over other neuroleptic drugs, such as haloperidol and risperidone, which bind a range of targets including four of the five known dopamine receptor subtypes (D1-4), serotonin (5-HT2A, 2C), α1- and α2-adrenergic, and histamine H1 receptors. Compared to these drugs, tiapride has a relatively moderate affinity for its target receptors, displacing 50 percent of 3H-raclopride binding at a concentration of 320 nM at D2 receptors and a concentration of 180 nM at D3 receptors.
Target Actions Organism ADopamine D2 receptor blockerHumans ADopamine D3 receptor blockerHumans ASerotonin Receptors antagonistHumans AAlpha-1 adrenergic receptors antagonistHumans AAlpha-2 adrenergic receptors antagonistHumans - Absorption
The bioavailability of tiapride is approximately 75 percent. It has a Tmax is 0.4-1.5 hours and Tss is 24-48 hours with 3 time daily dosing. Benzamide and its derivatives are highly water-soluble but known to cross the blood-brain barrier, necessitating carrier-mediated transport.
- Volume of distribution
Tiapride distributes rapidly and exhibits virtually no binding to plasma proteins, giving it a relatively high volume of distribution
- Protein binding
Negligible
- Metabolism
Tiapride is minimally metabolized in humans, 70 % of the drug is eliminated in unchanged form in the urine within 24 hours. Only low concentration of N-desethyl tiapride and tiapride N-oxide and no phase II metabolites were detected.
- Route of elimination
Urine (70% as unchanged tiapride)
- Half-life
2.9–3.6 hours
- Clearance
16.6 l/h.
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with Tiapride. Abacavir Abacavir may decrease the excretion rate of Tiapride which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Tiapride which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Tiapride which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Tiapride which could result in a higher serum level. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Tiapride. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Tiapride. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Tiapride which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Tiapride which could result in a higher serum level. Acrivastine Acrivastine may decrease the excretion rate of Tiapride which could result in a higher serum level. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Tiapride hydrochloride 25N106WEDO 51012-33-0 OTFDPNXIVHBTKW-UHFFFAOYSA-N - International/Other Brands
- Gramalil / Italprid / Luxoben / Sereprile / Tiapridal
Categories
- ATC Codes
- N05AL03 — Tiapride
- Drug Categories
- Acids, Carbocyclic
- Amines
- Antipsychotic Agents
- Benzamides and benzamide derivatives
- Benzene Derivatives
- Benzoates
- Central Nervous System Agents
- Central Nervous System Depressants
- Dopamine Agents
- Dopamine Antagonists
- Dopamine D2 Receptor Antagonists
- Drugs that are Mainly Renally Excreted
- Ethylamines
- Nervous System
- Neurotoxic agents
- Neurotransmitter Agents
- Psycholeptics
- Psychotropic Drugs
- Tranquilizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonyl compounds
- Direct Parent
- Benzenesulfonyl compounds
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Anisoles / Alkyl aryl ethers / Sulfones / Trialkylamines / Propargyl-type 1,3-dipolar organic compounds / Carboximidic acids / Organopnictogen compounds / Organic oxides show 1 more
- Substituents
- Alkyl aryl ether / Amine / Anisole / Aromatic homomonocyclic compound / Benzenesulfonyl group / Carboximidic acid / Carboximidic acid derivative / Ether / Hydrocarbon derivative / Methoxybenzene show 15 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- LAH70H9JPH
- CAS number
- 51012-32-9
- InChI Key
- JTVPZMFULRWINT-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- N-[2-(diethylamino)ethyl]-5-methanesulfonyl-2-methoxybenzamide
- SMILES
- CCN(CC)CCNC(=O)C1=CC(=CC=C1OC)S(C)(=O)=O
References
- General References
- Scatton B, Cohen C, Perrault G, Oblin A, Claustre Y, Schoemaker H, Sanger DJ, Rouquier L, Porsolt R: The preclinical pharmacologic profile of tiapride. Eur Psychiatry. 2001 Jan;16 Suppl 1:29s-34s. [Article]
- Dose M, Lange HW: The benzamide tiapride: treatment of extrapyramidal motor and other clinical syndromes. Pharmacopsychiatry. 2000 Jan;33(1):19-27. [Article]
- Bischoff S, Bittiger H, Delini-Stula A, Ortmann R: Septo-hippocampal system: target for substituted benzamides. Eur J Pharmacol. 1982 Apr 23;79(3-4):225-32. [Article]
- Norman T, Chiu E, James RH, Gregory MS: Single oral dose pharmacokinetics of tiapride in patients with Huntington's disease. Eur J Clin Pharmacol. 1987;32(6):583-6. [Article]
- AIFA Product Information: Sereprile (tiapride hydrochloride) solution for injection [Link]
- External Links
- Human Metabolome Database
- HMDB0042039
- KEGG Drug
- D08590
- PubChem Compound
- 5467
- PubChem Substance
- 347829159
- ChemSpider
- 5268
- BindingDB
- 82073
- 10588
- ChEBI
- 94666
- ChEMBL
- CHEMBL84158
- ZINC
- ZINC000001542927
- Wikipedia
- Tiapride
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Gilles de la Tourette's Syndrome / Tic Disorder, Chronic Motor or Vocal / Tic Disorders 1 3 Completed Treatment Huntington's Disease (HD) 1 3 Terminated Treatment Anxiety Disorders / Dementia / Depression / Psychosomatic Disorders / Schizophrenia 1 3 Unknown Status Treatment Psychosis Nos/Other 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Injection, solution Intramuscular 100 mg Injection, solution Intramuscular; Intravenous 100 MG/2ML Solution / drops Oral 150 MG/ML Tablet 100 MG Injection Tablet 200 MG Tablet, film coated Oral 100 MG Tablet, film coated Oral 200 MG Solution / drops; suspension / drops Oral 137.9 mg/mL - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.252 mg/mL ALOGPS logP 1.14 ALOGPS logP 0.46 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 13.23 Chemaxon pKa (Strongest Basic) 8.87 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 75.71 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 88.02 m3·mol-1 Chemaxon Polarizability 35.58 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Blocker
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Scatton B, Cohen C, Perrault G, Oblin A, Claustre Y, Schoemaker H, Sanger DJ, Rouquier L, Porsolt R: The preclinical pharmacologic profile of tiapride. Eur Psychiatry. 2001 Jan;16 Suppl 1:29s-34s. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Blocker
- General Function
- G-protein coupled amine receptor activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
- Gene Name
- DRD3
- Uniprot ID
- P35462
- Uniprot Name
- D(3) dopamine receptor
- Molecular Weight
- 44224.335 Da
References
- Scatton B, Cohen C, Perrault G, Oblin A, Claustre Y, Schoemaker H, Sanger DJ, Rouquier L, Porsolt R: The preclinical pharmacologic profile of tiapride. Eur Psychiatry. 2001 Jan;16 Suppl 1:29s-34s. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Components:
References
- Scatton B, Cohen C, Perrault G, Oblin A, Claustre Y, Schoemaker H, Sanger DJ, Rouquier L, Porsolt R: The preclinical pharmacologic profile of tiapride. Eur Psychiatry. 2001 Jan;16 Suppl 1:29s-34s. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Components:
| Name | UniProt ID |
|---|---|
| Alpha-1A adrenergic receptor | P35348 |
| Alpha-1B adrenergic receptor | P35368 |
| Alpha-1D adrenergic receptor | P25100 |
References
- Scatton B, Cohen C, Perrault G, Oblin A, Claustre Y, Schoemaker H, Sanger DJ, Rouquier L, Porsolt R: The preclinical pharmacologic profile of tiapride. Eur Psychiatry. 2001 Jan;16 Suppl 1:29s-34s. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Components:
| Name | UniProt ID |
|---|---|
| Alpha-2A adrenergic receptor | P08913 |
| Alpha-2B adrenergic receptor | P18089 |
| Alpha-2C adrenergic receptor | P18825 |
References
- Scatton B, Cohen C, Perrault G, Oblin A, Claustre Y, Schoemaker H, Sanger DJ, Rouquier L, Porsolt R: The preclinical pharmacologic profile of tiapride. Eur Psychiatry. 2001 Jan;16 Suppl 1:29s-34s. [Article]
Drug created at October 21, 2016 02:08 / Updated at June 12, 2021 10:54