Details of the Drug

General Information of Drug (ID: DMY9P37)

Drug Name
Flupenthixol
Synonyms
Depixol; Emergil; Fluanxol; Fluxanxol; Siplaril; Siplarol; LC 44; N 7009; ALPHA-FLUPENTHIXOL; Cis(Z)Flupenthixol; Cis-Flupenthixol; Cis-Flupentixol; Depixol (TN); Fluanxol (TN); Flupentixol (INN); Flupentixol [INN:DCF]; Flupentixolum [INN-Latin]; Cis-(Z)-Flupenthixol; (Z)-4-(3-(2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene)propyl)-1-piperazineethanol; (Z)-4-(3-(2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene)propyl)piperazine-1-ethanol; 1-Piperazineethanol, 4-(3-(2-(trifluoromethyl)-9H-thioxanthen-9-ylidene)propyl)-(9CI); 2-Trifluoromethyl-9-(3-(4-(2-hydroxyethyl)piperazin-1-yl)propylidene)thioxanthene; 2-Trifluoromethyl-9-(3-(4-(beta-hydroxyethyl)-1-piperazinyl)propylidene)thioxanthene; 2-[4-[(3Z)-3-[2-(Trifluoromethyl)thioxanthen-9-ylidene]propyl]piperazin-1-yl]ethanol; 4-(3-(2-(Trifluoromethyl)-9H-thioxanthen-9-ylidene)propyl)-1-piperazineethanol; 4-(3-(2-(Trifluoromethyl)thioxanthen-9-ylidene)propyl)-1-piperazineethanol
Indication
Disease Entry ICD 11 Status REF
Schizophrenia 6A20 Withdrawn from market [1], [2]
Therapeutic Class
Antipsychotic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 434.5
Topological Polar Surface Area (xlogp) 4.5
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 4.14 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 34.2 hours [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.1 micromolar/kg/day [4]
Chemical Identifiers
Formula
C23H25F3N2OS
IUPAC Name
2-[4-[(3Z)-3-[2-(trifluoromethyl)thioxanthen-9-ylidene]propyl]piperazin-1-yl]ethanol
Canonical SMILES
C1CN(CCN1CC/C=C\\2/C3=CC=CC=C3SC4=C2C=C(C=C4)C(F)(F)F)CCO
InChI
InChI=1S/C23H25F3N2OS/c24-23(25,26)17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)30-22)5-3-9-27-10-12-28(13-11-27)14-15-29/h1-2,4-8,16,29H,3,9-15H2/b18-5-
InChIKey
NJMYODHXAKYRHW-DVZOWYKESA-N
Cross-matching ID
PubChem CID
5281881
ChEBI ID
CHEBI:10454
CAS Number
53772-82-0
DrugBank ID
DB00875
TTD ID
D0OC3J

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 [5], [6]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Schizophrenia
ICD Disease Classification 6A20
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) Jump to Detail Molecular Expression Atlas of This Drug

References

1 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: 968).
2 Behavioral responses of dopamine beta-hydroxylase knockout mice to modafinil suggest a dual noradrenergic-dopaminergic mechanism of action. Pharmacol Biochem Behav. 2008 Dec;91(2):217-22.
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 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
5 A role for medial prefrontal dopaminergic innervation in instrumental conditioning. J Neurosci. 2009 May 20;29(20):6599-606.
6 Atypical antipsychotics: mechanism of action. Can J Psychiatry. 2002 Feb;47(1):27-38.
7 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.
8 Dopaminergic synapses in the matrix of the ventrolateral striatum after chronic haloperidol treatment. Synapse. 2002 Aug;45(2):78-85.
9 CYP2D6 and DRD2 genes differentially impact pharmacodynamic sensitivity and time course of prolactin response to perphenazine. Pharmacogenet Genomics. 2007 Nov;17(11):989-93.
10 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.
11 Screening of domperidone in wastewater by high performance liquid chromatography and solid phase extraction methods. Talanta. 2006 Jan 15;68(3):928-31.
12 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).
13 Receptor reserve-dependent properties of antipsychotics at human dopamine D2 receptors. Eur J Pharmacol. 2009 Apr 1;607(1-3):35-40.
14 [The benzamides tiapride, sulpiride, and amisulpride in treatment for Tourette's syndrome]. Nervenarzt. 2007 Mar;78(3):264, 266-8, 270-1.
15 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.
16 Hughes B: 2009 FDA drug approvals. Nat Rev Drug Discov. 2010 Feb;9(2):89-92.