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Eltoprazine

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Chemical compound Pharmaceutical compound
Eltoprazine
Clinical data
Other namesDU-28,853; DU-28853
ATC code
  • None
Identifiers
IUPAC name
  • 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H16N2O2
Molar mass220.272 g·mol
3D model (JSmol)
SMILES
  • C1CN(CCN1)C2=C3C(=CC=C2)OCCO3
InChI
  • InChI=1S/C12H16N2O2/c1-2-10(14-6-4-13-5-7-14)12-11(3-1)15-8-9-16-12/h1-3,13H,4-9H2
  • Key:WVLHGCRWEHCIOT-UHFFFAOYSA-N

Eltoprazine (developmental code name DU-28,853) is a serotonergic drug of the phenylpiperazine class which is described as a serenic, or anti-aggressive agent.

It acts as an agonist of the serotonin 5-HT1A and 5-HT1B receptors and as an antagonist of the serotonin 5-HT2C receptor. The drug is closely related to fluprazine and batoprazine, which are similarly acting agents, and is also a known chemical precursor to S-15535 and lecozotan.

Eltoprazine is or was under development for the treatment of aggression, attention deficit hyperactivity disorder (ADHD), cognitive disorders, and drug-induced dyskinesia, but no recent development has been reported for these indications as of February 2022. It was also under development for the treatment of psychotic disorders, but development for this indication was discontinued. Eltoprazine was originated by Solvay and was developed by Elto Pharma, PsychoGenics, and Solvay.

References

  1. ^ "Eltoprazine - Elto Pharma - AdisInsight".
  2. Olivier B, Mos J, Rasmussen D (1990). "Behavioural pharmacology of the serenic, eltoprazine". Drug Metabol Drug Interact. 8 (1–2): 31–83. doi:10.1515/DMDI.1990.8.1-2.31. PMID 2091890. S2CID 27279453.
  3. ^ de Boer SF, Koolhaas JM (December 2005). "5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis". Eur J Pharmacol. 526 (1–3): 125–39. doi:10.1016/j.ejphar.2005.09.065. PMID 16310183.
  4. Schipper J, Tulp MT, Sijbesma H (1990). "Neurochemical profile of eltoprazine". Drug Metabol Drug Interact. 8 (1–2): 85–114. doi:10.1515/dmdi.1990.8.1-2.85. PMID 1982626. S2CID 30096596.

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Serotonin receptor modulators
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT37
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Piperazines
Simple piperazines
(no additional rings)
Phenylpiperazines
Benzylpiperazines
Diphenylalkylpiperazines
(benzhydrylalkylpiperazines)
Pyrimidinylpiperazines
Pyridinylpiperazines
Benzo(iso)thiazolylpiperazines
Tricyclics
(piperazine attached via side chain)
Others/Uncategorized
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