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Schizophrenia	6A20	Withdrawn from market	[1]
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Therapeutic Class

Antipsychotic Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

434.5

Logarithm of the Partition Coefficient (xlogp)

4.5

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Clearance: The drug present in the plasma can be removed from the body at the rate of 4.14 mL/min/kg [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 34.2 hours [2]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.1 micromolar/kg/day [3]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Tardive dyskinesia	Not Available	DRD2	OTBLXKEG	[4]
Tardive dyskinesia	Not Available	DRD3	OT0OFFKB	[4]
Tardive dyskinesia	Not Available	DRD4	OTAJTO7N	[4]
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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]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
D(2) dopamine receptor (DRD2)	OTBLXKEG	DRD2_HUMAN	Drug Response	[4]
D(3) dopamine receptor (DRD3)	OT0OFFKB	DRD3_HUMAN	Drug Response	[4]
D(4) dopamine receptor (DRD4)	OTAJTO7N	DRD4_HUMAN	Drug Response	[4]

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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

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)

MEA Detail

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	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3	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
4	ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
5	A role for medial prefrontal dopaminergic innervation in instrumental conditioning. J Neurosci. 2009 May 20;29(20):6599-606.