Enpiprazole

Last updated
Enpiprazole
Enpiprazole.png
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 1-(2-Chlorophenyl)-4-[2-(1-methyl-1H-pyrazol-4-yl)ethyl]piperazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H21ClN4
Molar mass 304.82 g·mol−1
3D model (JSmol)
  • Clc3ccccc3N2CCN(CCc1cn(nc1)C)CC2

Enpiprazole (INN, BAN) is an anxiolytic drug of the phenylpiperazine group that was never marketed. [1] [2] It produces anxiolytic-like effects in animals, though these effects appear to be biphasic and may reverse at high doses. [3] It is known to produce ortho-chlorophenylpiperazine (oCPP) as a metabolite. [4]

See also

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Mepiprazole is an anxiolytic drug of the phenylpiperazine group with additional antidepressant properties that is marketed in Spain. It acts as a 5-HT2A and α1-adrenergic receptor antagonist and inhibits the reuptake and induces the release of serotonin, dopamine, and norepinephrine to varying extents, and has been described as a serotonin antagonist and reuptake inhibitor (SARI). Controlled clinical trials of mepiprazole in patients with irritable bowel syndrome (IBS) were also carried out and suggested some benefits of the drug in relieving symptoms of IBS in some patients. Similarly to other phenylpiperazines like trazodone, nefazodone, and etoperidone, mepiprazole produces mCPP as an active metabolite.

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Enciprazine is an anxiolytic and antipsychotic of the phenylpiperazine class which was never marketed. It shows high affinity for the α1-adrenergic receptor and 5-HT1A receptor, among other sites. The drug was initially anticipated to produce ortho-methoxyphenylpiperazine (oMeOPP), a serotonin receptor agonist with high affinity for the 5-HT1A receptor, as a significant active metabolite, but subsequent research found this not to be the case.

References

  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 488–. ISBN   978-1-4757-2085-3.
  2. Bernan, British Pharmacopoeia Commission (2002). British Approved Names 2002. United Kingdom: The Stationery Office. p. 359. ISBN   0-11-322558-X.
  3. Murasaki M, Hara T, Oguchi T, Inami M, Ikeda Y (September 1976). "Action of enpiprazole on emotional behavior induced by hypothalamic stimulation in rats and cats". Psychopharmacology. 49 (3): 271–4. doi:10.1007/BF00426829. PMID   12526. S2CID   10302402.
  4. B.L. Goodwin (10 November 2004). Handbook of Biotransformations of Aromatic Compounds. CRC Press. pp. 3–. ISBN   978-0-203-64196-5.