ETOPERIDONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H28ClN5O
Molecular Weight	377.912
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN1C(=O)N(CCCN2CCN(CC2)C3=CC(Cl)=CC=C3)N=C1CC

InChI

InChIKey=IZBNNCFOBMGTQX-UHFFFAOYSA-N

InChI=1S/C19H28ClN5O/c1-3-18-21-25(19(26)24(18)4-2)10-6-9-22-11-13-23(14-12-22)17-8-5-7-16(20)15-17/h5,7-8,15H,3-4,6,9-14H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C19H28ClN5O
Molecular Weight	377.912
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11765144 | https://www.ncbi.nlm.nih.gov/pubmed/12487725 | https://www.ncbi.nlm.nih.gov/pubmed/29053130 | https://www.ncbi.nlm.nih.gov/pubmed/7766726 |

Etoperidone is an atypical antidepressant introduced in Europe in 1977. The activity of etoperidone is made mainly by its major metabolite 1-(3'-chlorophenyl)piperazine (mCPP). mCPP binds with different affinity to most of the serotonergic receptors and adrenergic receptors. This metabolite is an agonist of 5-HT2c and an antagonist of 5-HT2a. Part of etoperidone structure contributes to the activity in the α-adrenergic receptors. Etoperidone has been studied for the treatment of depression, tremors in Parkinson, extrapyramidal symptoms and male impotence. It is not certain if it was ever approved and marketed but its current status is withdrawn.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Adrenergic receptor alpha-1 169 Target ID: CHEMBL2094251 Sources: https://www.drugbank.ca/drugs/DB09194	Antagonist 2778	38.0 nM [Kd]
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.drugbank.ca/drugs/DB09194	Antagonist 2778	570.0 nM [Kd]
Dopamine D2 receptor 297 Target ID: CHEMBL217 Sources: https://www.drugbank.ca/drugs/DB09194\|http://drugcentral.org/drugcard/1111	Antagonist 2778	2.3 µM [Kd]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.drugbank.ca/drugs/DB09194\|http://drugcentral.org/drugcard/1111	Antagonist 2778	85.0 nM [Kd]
Serotonin 2 (5-HT2) receptor 87 Target ID: CHEMBL2095200 Sources: https://www.drugbank.ca/drugs/DB09194\|http://drugcentral.org/drugcard/1111	Antagonist 2778	36.0 nM [Kd]

PubMed

Title	Date	PubMed
Binding of antidepressants to human brain receptors: focus on newer generation compounds.	1994 May	7855217
Pharmacological profile of antidepressants and related compounds at human monoamine transporters.	1997 Dec 11	9537821
Thioridazine for dementia.	2001	11686961
Evaluation of the absorption, excretion and metabolism of [14C] etoperidone in man.	2001 Nov	11765144
In vitro identification of metabolic pathways and cytochrome P450 enzymes involved in the metabolism of etoperidone.	2002 Nov	12487725
A comparative solid-phase extraction study for the simultaneous determination of fluvoxamine, mianserin, doxepin, citalopram, paroxetine, and etoperidone in whole blood by capillary gas-liquid chromatography with nitrogen-phosphorus detection.	2004 Apr	15107147
Tamoxifen's protection against breast cancer recurrence is not reduced by concurrent use of the SSRI citalopram.	2008 Aug 19	18665165
Detection of novel reactive metabolites of trazodone: evidence for CYP2D6-mediated bioactivation of m-chlorophenylpiperazine.	2008 May	18238857
5-(4-Chloro-phen-yl)-3-(2,4-dimethyl-thiazol-5-yl)-1,2,4-triazolo[3,4-a]isoquinoline.	2010 Apr 10	21579114

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:04:47 GMT 2023` Edited by `admin` on `Sat Dec 16 17:04:47 GMT 2023`
Record UNII	KAI6MVO39Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETOPERIDONE

Official Name

English

1-(3-(4-(M-CHLOROPHENYL)-1-PIPERAZINYL)PROPYL)-3,4-DIETHYL-D2-1,2,4-TRIAZOLIN-5-ONE

Common Name

English

Etoperidone [WHO-DD]

Common Name

English

etoperidone [INN]

Common Name

English

ETOPERIDONE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN06AB09