Chemistry:Indeloxazine

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Short description: Antidepressant and cerebral activator
Indeloxazine
Indeloxazine.svg
Clinical data
Other namesCI-874, YM-08054
ATC code
  • None
Legal status
Legal status
  • Discontinued
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
Chemical and physical data
FormulaC14H17NO2
Molar mass231.295 g·mol−1
3D model (JSmol)
  (verify)

Indeloxazine (INN) (Elen, Noin) is an antidepressant and cerebral activator[1][2] that was marketed in Japan and South Korea by Yamanouchi Pharmaceutical Co., Ltd for the treatment of psychiatric symptoms associated with cerebrovascular diseases, namely depression resulting from stroke, emotional disturbance, and avolition.[3][4] It was marketed from 1988[4] to 1998, when it was removed from the market reportedly for lack of effectiveness.[5]

Indeloxazine acts as a serotonin releasing agent, norepinephrine reuptake inhibitor, and NMDA receptor antagonist.[6][7] It has been found to enhance acetylcholine release in the rat forebrain through activation of the 5-HT4 receptor via its action as a serotonin releasing agent.[8][9][10] The drug has been found to possess nootropic,[11][12] neuroprotective,[13][14][15][16] anticonvulsant,[17] and antidepressant-like effects in animal models.[1][6]

References

  1. ↑ 1.0 1.1 "Syntheses of (+/-)-2-[(inden-7-yloxy)methyl]morpholine hydrochloride (YM-08054, indeloxazine hydrochloride) and its derivatives with potential cerebral-activating and antidepressive properties". Chemical & Pharmaceutical Bulletin 33 (9): 3766–3774. September 1985. doi:10.1248/cpb.33.3766. PMID 4092278. 
  2. ↑ "Determination of indeloxazine, a new antidepressant agent, in human plasma by gas-liquid chromatography with electron-capture detection". Journal of Chromatography 272 (1): 176–180. January 1983. doi:10.1016/s0378-4347(00)86115-0. PMID 6841538. 
  3. ↑ Index nominum, international drug ... - Google Books. Taylor & Francis. 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&q=indeloxazine&pg=PA548. 
  4. ↑ 4.0 4.1 Dictionary of pharmacological agents - Google Books. CRC Press. 1997. ISBN 978-0-412-46630-4. https://books.google.com/books?id=A0THacd46ZsC&q=Indeloxazine. 
  5. ↑ "Drug approval in Japan questioned". Lancet 352 (9126): 491. August 1998. doi:10.1016/s0140-6736(05)79232-1. PMID 9708787. 
  6. ↑ 6.0 6.1 "Neurochemical and behavioral characterization of potential antidepressant properties of indeloxazine hydrochloride". Neuropharmacology 37 (9): 1169–1176. September 1998. doi:10.1016/s0028-3908(98)00009-4. PMID 9833647. 
  7. ↑ "Effects of several cerebroprotective drugs on NMDA channel function: evaluation using Xenopus oocytes and [3H]MK-801 binding". European Journal of Pharmacology 207 (2): 119–128. June 1991. doi:10.1016/0922-4106(91)90086-w. PMID 1652446. 
  8. ↑ "Serotonin 5-HT4 receptors and forebrain cholinergic system: receptor expression in identified cell populations". Brain Structure & Function 220 (6): 3413–3434. November 2015. doi:10.1007/s00429-014-0864-z. PMID 25183542. 
  9. ↑ "Facilitation of acetylcholine release in rat frontal cortex by indeloxazine hydrochloride: involvement of endogenous serotonin and 5-HT4 receptors". Naunyn-Schmiedeberg's Archives of Pharmacology 356 (6): 712–720. December 1997. doi:10.1007/pl00005110. PMID 9453456. http://link.springer.de/link/service/journals/00210/bibs/7356006/73560712.htm. Retrieved 2010-01-11. 
  10. ↑ "Possible involvement of central cholinergic system in ameliorating effects of indeloxazine, a cerebral activator, on disturbance of learning behavior in rats". Progress in Neuro-Psychopharmacology & Biological Psychiatry 18 (3): 603–613. May 1994. doi:10.1016/0278-5846(94)90016-7. PMID 8078992. 
  11. ↑ "Comparison of the effects of bifemelane hydrochloride and indeloxazine hydrochloride on scopolamine hydrobromide-induced impairment in radial maze performance". Clinical Therapeutics 10 (6): 704–711. 1988. PMID 3219685. 
  12. ↑ "Cerebral activating properties of indeloxazine hydrochloride". Neuropharmacology 26 (7A): 761–770. July 1987. doi:10.1016/0028-3908(87)90239-5. PMID 3627384. 
  13. ↑ "Comparison of the effects of bifemelane hydrochloride, idebenone and indeloxazine hydrochloride on ischemia-induced depletion of brain acetylcholine levels in gerbils". Research Communications in Chemical Pathology and Pharmacology 61 (2): 285–288. August 1988. PMID 3187197. 
  14. ↑ "Protective effects of indeloxazine hydrochloride on cerebral ischemia in animals". Archives Internationales de Pharmacodynamie et de Therapie 290 (1): 16–24. November 1987. PMID 3446040. 
  15. ↑ "Anti-hypoxic and anti-ischemic actions of indeloxazine hydrochloride and its optical isomers: possible involvement of cerebral energy metabolism". Archives Internationales de Pharmacodynamie et de Therapie 324: 33–46. 1993. PMID 8297184. 
  16. ↑ "Effects of indeloxazine hydrochloride (YM-08054) on anoxia". Archives Internationales de Pharmacodynamie et de Therapie 286 (2): 272–281. April 1987. PMID 3592867. 
  17. ↑ "Effects of indeloxazine HCl on kindled amygdaloid seizures in rats: comparison with the effects of phenytoin, diazepam, ethanol, and imipramine". Pharmacology, Biochemistry, and Behavior 45 (2): 445–450. June 1993. doi:10.1016/0091-3057(93)90263-s. PMID 8327550. 



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