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{{Short description|Chemical compound}}
'''Eltoprazine''' (DU 28853) is a [[piperazine|phenylpiperazine]] and so-called '''serenic''', or '''antiaggressive''' [[drug]], used as a research chemical in scientific studies.<ref name="pmid2091890">{{cite journal | author = Olivier B, Mos J, Rasmussen D. | title = Behavioural pharmacology of the serenic, eltoprazine | journal = Drug Metabol Drug Interact. | volume = 8 | issue = 1-2 | pages = 31-83 | year = 1990 | pmid = 2091890 }}</ref> It is closely related to several other piperazines, including [[fluprazine]], [[batoprazine]], [[DU 28412]], [[flesinoxan]], and [[TFMPP]], as well as more distantly to the [[azapirone]]s such as [[buspirone]]. Eltoprazine acts as an [[agonist]] at the [[5-HT1A|5-HT<sub>1A</sub>]] and [[5-HT1B|5-HT<sub>1B</sub>]] receptors, and as an [[antagonist]] at the [[5-HT2C|5-HT<sub>2C</sub>]] receptor.<ref name="pmid1982626">{{cite journal | author = Schipper J, Tulp MT, Sijbesma H. | title = Neurochemical profile of eltoprazine. | journal = Drug Metabol Drug Interact. | volume = 8 | issue = 1-2 | pages = 85-114 | year = 1990 | pmid = 1982626 }}</ref> Its serenic properties may actually be mediated by anxiogenesis.<ref name="pmid11224163">{{cite journal | author = Rodgers RJ, Cole JC, Cobain MR, Daly P, Doran PJ, Eells JR, Wallis P. | title = Anxiogenic-like effects of fluprazine and eltoprazine in the mouse elevated plus-maze: profile comparisons with 8-OH-DPAT, CGS 12066B, TFMPP and mCPP. | journal = Behav Pharmacol. | volume = 3 | issue = 6 | pages = 621-634 | year = 1992 | pmid = 11224163 }}</ref>
{{Infobox drug
| drug_name =
| image = Eltoprazine.png
| width =
| caption =


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== References ==
| legal_status =
{{reflist}}


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<!-- Identifiers -->
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{{Serotonin agonists}}
| CAS_number = 98224-03-4
{{Serotonin antagonists}}
| CAS_supplemental =
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[[Category:Piperazines]]
| PubChem = 65853
| IUPHAR_ligand =
| DrugBank =
| ChemSpiderID = 59265
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 510M006KO6
| KEGG =
| ChEBI =
| ChEMBL = 282614
| NIAID_ChemDB =
| PDB_ligand =
| synonyms = DU-28,853; DU-28853

<!-- Chemical data -->
| IUPAC_name = 1-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine
| C=12 | H=16 | N=2 | O=2
| SMILES = C1CN(CCN1)C2=C3C(=CC=C2)OCCO3
| StdInChI = 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
| StdInChIKey = WVLHGCRWEHCIOT-UHFFFAOYSA-N
}}

'''Eltoprazine''' (developmental code name '''DU-28,853''') is a [[Serotonin|serotonergic]] [[drug]] of the [[phenylpiperazine]] class which is described as a [[serenic]] or anti[[aggressive]] agent.<ref name="AdisInsight" /><ref name="pmid2091890">{{cite journal | vauthors = Olivier B, Mos J, Rasmussen D | title = Behavioural pharmacology of the serenic, eltoprazine | journal = Drug Metabol Drug Interact. | volume = 8 | issue = 1–2 | pages = 31–83 | year = 1990 | pmid = 2091890 | doi=10.1515/DMDI.1990.8.1-2.31| s2cid = 27279453 }}</ref><ref name="pmid16310183">{{cite journal | vauthors = de Boer SF, Koolhaas JM | title = 5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis | journal = Eur J Pharmacol | volume = 526 | issue = 1–3 | pages = 125–39 | date = December 2005 | pmid = 16310183 | doi = 10.1016/j.ejphar.2005.09.065 | url = }}</ref> It acts as an [[agonist]] of the [[serotonin]] [[5-HT1A|5-HT<sub>1A</sub>]] and [[5-HT1B|5-HT<sub>1B</sub> receptor]]s and as an [[antagonist]] of the serotonin [[5-HT2C|5-HT<sub>2C</sub> receptor]].<ref name="pmid16310183" /><ref name="pmid1982626">{{cite journal | vauthors = Schipper J, Tulp MT, Sijbesma H | title = Neurochemical profile of eltoprazine. | journal = Drug Metabol Drug Interact. | volume = 8 | issue = 1–2 | pages = 85–114 | year = 1990 | pmid = 1982626 | doi=10.1515/dmdi.1990.8.1-2.85| s2cid = 30096596 }}</ref> The drug is closely related to [[fluprazine]] and [[batoprazine]], which are similarly acting agents, and is also a known [[precursor (chemistry)|chemical precursor]] to [[S-15535]] and [[lecozotan]]. Eltoprazine is or was under development for the treatment of [[aggression]], [[attention deficit hyperactivity disorder]] (ADHD), [[cognition disorder]]s, and [[drug-induced dyskinesia]], but no recent development has been reported for these indications as of February 2022.<ref name="AdisInsight">{{cite web | url=https://adisinsight.springer.com/drugs/800000719 | title=Eltoprazine - Elto Pharma - AdisInsight }}</ref> It was also under development for the treatment of [[psychotic disorder]]s, but development for this indication was discontinued.<ref name="AdisInsight" /> Eltoprazine was originated by [[Solvay S.A.|Solvay]] and was developed by [[Elto Pharma]], [[PsychoGenics]], and Solvay.<ref name="AdisInsight" />

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==References==
{{Reflist}}

==External links==
* {{Commonscatinline}}
* [https://adisinsight.springer.com/drugs/800000719 Eltoprazine - AdisInsight]

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{{Serotonin receptor modulators}}
{{Piperazines}}

[[Category:5-HT1A agonists]]
[[Category:5-HT1B agonists]]
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[[Category:5-HT2C antagonists]]
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[[Category:Benzodioxins]]
[[Category:Eltoprazines| ]]
[[Category:Experimental drugs]]
[[Category:1-Piperazinyl compounds]]
[[Category:Serotonin receptor agonists]]
[[Category:Serotonin receptor agonists]]
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[[Category:Serotonin antagonists]]

Latest revision as of 18:22, 24 July 2023

Eltoprazine
Clinical data
Other namesDU-28,853; DU-28853
Identifiers
  • 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−1
3D model (JSmol)
  • C1CN(CCN1)C2=C3C(=CC=C2)OCCO3
  • 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 antiaggressive agent.[1][2][3] It acts as an agonist of the serotonin 5-HT1A and 5-HT1B receptors and as an antagonist of the serotonin 5-HT2C receptor.[3][4] 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), cognition disorders, and drug-induced dyskinesia, but no recent development has been reported for these indications as of February 2022.[1] It was also under development for the treatment of psychotic disorders, but development for this indication was discontinued.[1] Eltoprazine was originated by Solvay and was developed by Elto Pharma, PsychoGenics, and Solvay.[1]

References

[edit]
  1. ^ a b c d "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. ^ a b 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.
[edit]
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