Details of the Drug

General Information of Drug (ID: DMN6CAG)

Drug Name

Tiapride

Synonyms

tiapride; 51012-32-9; Thiapride; Tiapridal; N-(2-(Diethylamino)ethyl)-2-methoxy-5-(methylsulfonyl)benzamide; Tiapridum [INN-Latin]; Tiaprida [INN-Spanish]; UNII-LAH70H9JPH; FLO 1347; Tiapride [INN:BAN:DCF]; Tiapride HCl; EINECS 256-907-9; LAH70H9JPH; BRN 2390588; JTVPZMFULRWINT-UHFFFAOYSA-N; BENZAMIDE, N-(2-(DIETHYLAMINO)ETHYL)-2-METHOXY-5-(METHYLSULFONYL)-; N-(2-(Diethylamino)ethyl)-5-(methylsulfonyl)-o-anisamide; Tiapridum; Tiaprida; Benzamide, N-[2-(diethylamino)ethyl]-2-methoxy-5-(methylsulfonyl)-; NCGC00015996-02; SPI-860

Indication

Disease Entry	ICD 11	Status	REF
Alcohol dependence	6C40.2	Approved	[1]
Neuropathic pain	8E43.0	Phase 1	[2]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

328.4

Topological Polar Surface Area (xlogp)

0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Clearance: The clearance of drug is 16.6 L/h [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.9C3.6 hours [5]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 21.7485 micromolar/kg/day [6]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.1 L/kg [5]

Chemical Identifiers

Formula: C15H24N2O4S
IUPAC Name: N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide
Canonical SMILES: CCN(CC)CCNC(=O)C1=C(C=CC(=C1)S(=O)(=O)C)OC
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)
InChIKey: JTVPZMFULRWINT-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 5467
ChEBI ID: CHEBI:94666
CAS Number: 51012-32-9
DrugBank ID: DB13025
TTD ID: D02LCR

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Dopamine D2 receptor (D2R)	TTEX248	DRD2_HUMAN	Antagonist	[7]
Voltage-gated sodium channel alpha Nav1.8 (SCN10A)	TT90XZ8	SCNAA_HUMAN	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Alcohol dependence

ICD Disease Classification

6C40.2

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Dopamine D2 receptor (D2R)	DTT	DRD2	2.50E-02	-0.08	-0.49

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Emerging drugs in neuropathic pain. Expert Opin Emerg Drugs. 2007 Mar;12(1):113-26.
3	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
4	An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
5	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7	The treatment of Tourette's syndrome: current opinions. Expert Opin Pharmacother. 2002 Jul;3(7):899-914.
8	Structures of muO-conotoxins from Conus marmoreus. I nhibitors of tetrodotoxin (TTX)-sensitive and TTX-resistant sodium channels in mammalian senso... J Biol Chem. 2004 Jun 11;279(24):25774-82.
9	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
10	Heterologous expression and functional analysis of rat Nav1.8 (SNS) voltage-gated sodium channels in the dorsal root ganglion neuroblastoma cell line ND7-23. Neuropharmacology. 2004 Mar;46(3):425-38.
11	Pathobiology of visceral pain: molecular mechanisms and therapeutic implications. II. Genetic approaches to pain therapy. Am J Physiol Gastrointest Liver Physiol. 2000 Apr;278(4):G507-12.
12	Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
13	Antibodies and venom peptides: new modalities for ion channels. Nat Rev Drug Discov. 2019 May;18(5):339-357.
14	Oral Administration of PF-01247324, a Subtype-Selective Nav1.8 Blocker, Reverses Cerebellar Deficits in a Mouse Model of Multiple Sclerosis. PLoS One. 2015; 10(3): e0119067.
15	The Detection of Dopamine Gene Receptors (DRD1-DRD5) Expression on Human Peripheral Blood Lymphocytes by Real Time PCR. Iran J Allergy Asthma Immunol. 2004 Dec;3(4):169-74.
16	Dopaminergic synapses in the matrix of the ventrolateral striatum after chronic haloperidol treatment. Synapse. 2002 Aug;45(2):78-85.
17	CYP2D6 and DRD2 genes differentially impact pharmacodynamic sensitivity and time course of prolactin response to perphenazine. Pharmacogenet Genomics. 2007 Nov;17(11):989-93.
18	Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. Bioorg Med Chem. 2005 Jan 3;13(1):77-87.
19	Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods. Talanta. 2006 Jan 15;68(3):928-31.
20	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 3639).
21	Receptor reserve-dependent properties of antipsychotics at human dopamine D2 receptors. Eur J Pharmacol. 2009 Apr 1;607(1-3):35-40.
22	[The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. Nervenarzt. 2007 Mar;78(3):264, 266-8, 270-1.
23	Modulatory role of dopamine D2 receptors and fundamental role of L-type Ca2+ channels in the induction of long-term potentiation in the basolateral... Eur J Pharmacol. 2009 Mar 15;606(1-3):90-3.
24	Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.