Flesinoxan

Last updated
Flesinoxan
Flesinoxan.svg
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
Identifiers
  • 4-fluoro-N-(2-{4-[(2S)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl}ethyl)benzamide
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
Formula C22H26FN3O4
Molar mass 415.465 g·mol−1
3D model (JSmol)
  • C1CN(CCN1CCNC(=O)C2=CC=C(C=C2)F)C3=C4C(=CC=C3)O[C@H](CO4)CO
  • InChI=1S/C22H26FN3O4/c23-17-6-4-16(5-7-17)22(28)24-8-9-25-10-12-26(13-11-25)19-2-1-3-20-21(19)29-15-18(14-27)30-20/h1-7,18,27H,8-15H2,(H,24,28)/t18-/m0/s1
  • Key:NYSDRDDQELAVKP-SFHVURJKSA-N

Flesinoxan (DU-29,373) is a potent and selective 5-HT1A receptor partial/near-full agonist of the phenylpiperazine class. [1] [2] [3] Originally developed as a potential antihypertensive drug, [1] [2] [4] flesinoxan was later found to possess antidepressant and anxiolytic effects in animal tests. [5] [6] As a result, it was investigated in several small human pilot studies for the treatment of major depressive disorder, and was found to have robust effectiveness and very good tolerability. [7] [8] However, due to "management decisions", the development of flesinoxan was stopped and it was not pursued any further. [9]

Contents

In patients, flesinoxan enhances REM sleep latency, decreases body temperature, and increases ACTH, cortisol, prolactin, and growth hormone secretion. [2] [8]

See also

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References

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  3. Hadrava V, Blier P, Dennis T, Ortemann C, de Montigny C (October 1995). "Characterization of 5-hydroxytryptamine1A properties of flesinoxan: in vivo electrophysiology and hypothermia study". Neuropharmacology. 34 (10): 1311–26. doi:10.1016/0028-3908(95)00098-Q. PMID   8570029. S2CID   27967032.
  4. Wouters W, Tulp MT, Bevan P (May 1988). "Flesinoxan lowers blood pressure and heart rate in cats via 5-HT1A receptors". European Journal of Pharmacology. 149 (3): 213–23. doi:10.1016/0014-2999(88)90651-6. PMID   2842163.
  5. van Hest A, van Drimmelen M, Olivier B (1992). "Flesinoxan shows antidepressant activity in a DRL 72-s screen". Psychopharmacology. 107 (4): 474–9. doi:10.1007/BF02245258. PMID   1351303. S2CID   6258207.
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  9. Celada P, Bortolozzi A, Artigas F (September 2013). "Serotonin 5-HT1A receptors as targets for agents to treat psychiatric disorders: rationale and current status of research". CNS Drugs. 27 (9): 703–16. doi:10.1007/s40263-013-0071-0. PMID   23757185. S2CID   31931009.