Etoperidone
Basic information
- CAS
52942-31-1- Standard SMILES
CCc1nn(CCCN2CCN(c3cccc(Cl)c3)CC2)c(=O)n1CC- InChIKey
IZBNNCFOBMGTQX-UHFFFAOYSA-N- Molecular formula
- C19H28ClN5O
- Average molar mass
- 377.9 g/mol
- Monoisotopic mass
- 377.1982382
Overview
Etoperidone is a member of piperazines.
Names & identifiers
- Preferred name
- Etoperidone
- IUPAC
- 2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one
- English name
- ETOPERIDONE
- Molecular formula
- C19H28ClN5O
- Molecular weight
- 377.91
Names & synonyms
ETOPERIDONE52942-31-1EtoperidonaEtoperidonumKAI6MVO39ZDTXSID0023034(1,3-(4-m-chlorophenyl-1-piperazinyl)propyl)-3,4-diethyl-delta(2)-1,2,4-triazolin-5-one1-{3-[4-(3-chlorophenyl)piperazin-1-yl]propyl}-3,4-diethyl-4,5-dihydro-1H-1,2,4-triazol-5-one1-(3-(4-(3-chlorophenyl)piperazin-1-yl)propyl)-3,4-diethyl-4,5-dihydro-1H-1,2,4-triazol-5-oneRefChem:139281DTXCID803034N06AB09
Show more names
2-[3-[4-(3-Chlorophenyl)-1-piperazinyl]propyl]-4,5-diethyl-2H-1,2,4-triazol-3(4H)-one3H-1,2,4-Triazol-3-one, 2-[3-[4-(3-chlorophenyl)-1-piperazinyl]propyl]-4,5-diethyl-2,4-dihydro-
2-(3-(4-(m-chlorophenyl)-1-piperazinyl)propyl)-4,5-diethyl-2,4-dihydro-3H-1,2,4-triazolo-3-one.HClEtoperidone [INN]2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-oneEtoperidona [Spanish]UNII-KAI6MVO39ZEtoperidonum [INN-Latin]Etoperidona [INN-Spanish]IZBNNCFOBMGTQX-UHFFFAOYSA-N
Database identifiers
- CAS
52942-31-1- PubChem CID
- 40589
- DTXSID
DTXSID0023034- ChEMBL
CHEMBL1743259- ChEBI
CHEBI:135589- UNII
- KAI6MVO39Z
- Nikkaji
- J9.735G
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 42.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 506
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Boiling Point499ºC at 760mmHg
Melting Point197-198 ºC
Physicochemical properties
- Boiling point
- 0.5 · bp0.5 230°
- form
- Oil
- FDA UNII
- 6 MVO39Z · KAI6MVO39Z
- ATC code
- 6 AB09 · N06AB09
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Protein BindingEtoperidone presents an extensive plasma protein binding.
Pharmacodynamics
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 α-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.
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 α-adrenergic receptors.
Biological Half-LifeAfter oral administration of etoperidone the terminal half-life was 21.7 hours.
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 2-[3-[4-(3-chloro-4-hydroxyphenyl)piperazin-1-yl]propyl]-4,5-diethyl-1,2,4-triazol-3-one, 2-[3-[4-(3-Chlorophenyl)piperazin-1-yl]propyl]-4-ethyl-5-(1-hydroxyethyl)-1,2,4-triazol-3-one, 4,5-diethyl-2-propyl-1,2,4-triazol-3-one, and 1-(3-Chlorophenyl)piperazine.
Absorption, Distribution and Excretion
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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