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Chemistry

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Also known as: 52942-31-1, Etoperidone [inn], Kai6mvo39z, 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one, Etoperidona, Etoperidonum
Molecular Formula
C19H28ClN5O
Molecular Weight
377.9  g/mol
InChI Key
IZBNNCFOBMGTQX-UHFFFAOYSA-N
FDA UNII
KAI6MVO39Z

Etoperidone
Etoperidone is an atypical antidepressant introduced in Europe in 1977. It is a phenylpiperazine-substituted triazole derivative with a composition that classifies it as an analog of tradozone and presents a similar pharmacological profile. Etoperidone was developed by Angelini Francesco ACRAF.
1 2D Structure

Etoperidone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one
2.1.2 InChI
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
2.1.3 InChI Key
IZBNNCFOBMGTQX-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC1=NN(C(=O)N1CC)CCCN2CCN(CC2)C3=CC(=CC=C3)Cl
2.2 Other Identifiers
2.2.1 UNII
KAI6MVO39Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (1,3-(4-m-chlorophenyl-1-piperazinyl)propyl)-3,4-diethyl-delta(2)-1,2,4-triazolin-5-one

2. Etoperidone Monohydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 52942-31-1

2. Etoperidone [inn]

3. Kai6mvo39z

4. 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one

5. Etoperidona

6. Etoperidonum

7. Etoperidona [spanish]

8. Unii-kai6mvo39z

9. Etoperidonum [inn-latin]

10. Etoperidona [inn-spanish]

11. Etoperidone [mi]

12. Schembl49314

13. Etoperidone [who-dd]

14. Chembl1743259

15. Dtxsid0023034

16. Bdbm82438

17. Chebi:135589

18. Zinc3830815

19. Nsc_40589

20. Pdsp1_000523

21. Pdsp2_000521

22. Db09194

23. Cas_52942-31-1

24. L001188

25. Q5404839

26. 1,2,4-triazol-3-one, 2-(3-(4-(3-chlorophenyl)-1-piperazinyl)propyl)-4,5-diethyl-2,4-dihydro-

27. 1-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-3,4-diethyl-d2-1,2,4-triazolin-5-one

28. 2-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-4,5-diethyl-2,4-dihydro-3h-1,2,4-triazol-3-one

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 377.9 g/mol
Molecular Formula C19H28ClN5O
XLogP33
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count7
Exact Mass377.1982382 g/mol
Monoisotopic Mass377.1982382 g/mol
Topological Polar Surface Area42.4 Ų
Heavy Atom Count26
Formal Charge0
Complexity506
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

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.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Etoperidone has a biphasic effect on the central transmission of serotonin. It presents the capacity to inhibit serotonin receptor but also to inhibit the reuptake of serotonin, norepinephrine and dopamine. As part of its actions, etoperidone also inhibits the -adrenergic receptors which directly corresponds to the sedative and cardiovascular effects. The presence of both effects caused that the effective dose of etoperidone was poorly tolerated thus, efforts have been made to separate the serotonergic and adrenergic functions in order to generate etoperidone-derivatives like nefazodone.


5.2 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AB - Selective serotonin reuptake inhibitors

N06AB09 - Etoperidone


5.3 Absorption, Distribution and Excretion

Absorption

The absorption and bioavailability is highly variable between individuals and can be as low as 12%. The lower bioavailability is explained due to its high metabolism. The mean time to peak plasma concentration is ranged from 1.4-4.8 hours.


Route of Elimination

The elimination of an oral dose of etoperidone presents a division of 78.8% found in urine and 9.6% found in faeces. On the elimination route, less than 0.01% of the etoperidone dose is represented by the unchanged drug while the rest is formed by 21 different metabolites.


Volume of Distribution

The high protein binding presented in etoperidone modulates its volume of distribution to a range of 0.23 to 0.69 L/kg.


Clearance

The apparent clearance of etoperidone was 1.01 ml/min.


5.4 Metabolism/Metabolites

Etoperidone is highly metabolized and it forms 21 different metabolites that can be found in plasma, urine and faeces. The metabolism of etoperidone is thought to be related to 5 different reaction pathways that are alkyl oxidation, piperazinyl oxidation, N-dealkylation, phenyl hydroxylation and conjugation.


Etoperidone has known human metabolites that include 1-(3-Chlorophenyl)piperazine, 2-[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]-4-ethyl-5-(1-hydroxyethyl)-1,2,4-triazol-3-one, 2-[3-[4-(3-chloro-4-hydroxyphenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one, and 4,5-diethyl-2-propyl-1,2,4-triazol-3-one.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.5 Biological Half-Life

After oral administration of etoperidone the terminal half-life was 21.7 hours.


5.6 Mechanism of Action

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 contibutes to the activity in the -adrenergic receptors.


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