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Tipepidine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Tipepidine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
Identifiers
  • 3-(di-2-thienylmethylene)-1-methylpiperidine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H17NS2
Molar mass275.43 g·mol−1
3D model (JSmol)
  • s1cccc1/C(c2sccc2)=C3\CCCN(C)C3
  • InChI=1S/C15H17NS2/c1-16-8-2-5-12(11-16)15(13-6-3-9-17-13)14-7-4-10-18-14/h3-4,6-7,9-10H,2,5,8,11H2,1H3 checkY
  • Key:JWIXXNLOKOAAQT-UHFFFAOYSA-N checkY
  (verify)

Tipepidine (INN; also known astipepidine hibenzate (JAN); brand namesAsverin,Antupex,Asvelik,Asvex,Bitiodin,Cofdenin A,Hustel,Nodal, andSotal) is asynthetic, non-opioidantitussive andexpectorant of thethiambutene class.[1][2] It acts as aninhibitor ofG protein-coupled inwardly-rectifying potassium channels (GIRKs).[3] The drug was discovered in the 1950s,[4] and was developed inJapan in 1959.[5] It is used as thehibenzate andcitrate salts.[1][5]

The usual dose is 20 mg every 4–6 hours.[citation needed] Possibleside effects of tipepidine, especially inoverdose, may includedrowsiness,vertigo,delirium,disorientation,loss of consciousness, andconfusion.[5]

Tipepidine has been investigated as a potentialpsychiatric drug. It is being investigated indepression,[3][6][7]obsessive-compulsive disorder,[8] andattention-deficit hyperactivity disorder (ADHD).[9][10][11] Through inhibition of GIRK channels, tipepidine increasesdopamine levels in thenucleus accumbens, but withoutincreasing locomotor activity or producingmethamphetamine-likebehavioral sensitization, and this action appears to be at least partly responsible for itsantidepressant-like effects in rodents.[12][13]

See also

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References

[edit]
  1. ^abGanellin CR, Triggle DJ (21 November 1996).Dictionary of Pharmacological Agents. CRC Press. pp. 1988–.ISBN 978-0-412-46630-4.
  2. ^Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1649–.ISBN 978-3-88763-075-1.
  3. ^abKawaura K, Ogata Y, Inoue M, Honda S, Soeda F, Shirasaki T, Takahama K (December 2009)."The centrally acting non-narcotic antitussive tipepidine produces antidepressant-like effect in the forced swimming test in rats".Behavioural Brain Research.205 (1):315–318.doi:10.1016/j.bbr.2009.07.004.PMID 19616036.S2CID 29236491.
  4. ^ES 272195, "Procedure for the preparation of a new piperidine derivative of anti-nutritional activity", published 1 March 1962, assigned to Antonio Gallardo SA. 
  5. ^abcImai Y, Ishii W, Endo A, Arakawa C, Kohira R, Fujita Y, et al. (October 2011). "Tipepidine hibenzate intoxication".Pediatrics International.53 (5):779–781.doi:10.1111/j.1442-200X.2010.03297.x.PMID 21955016.S2CID 205484528.
  6. ^Kawaura K, Honda S, Soeda F, Shirasaki T, Takahama K (May 2010)."[Novel antidepressant-like action of drugs possessing GIRK channel blocking action in rats]".Yakugaku Zasshi.130 (5):699–705.doi:10.1248/yakushi.130.699.PMID 20460867.
  7. ^Sasaki T, Hashimoto K, Tachibana M, Kurata T, Kimura H, Komatsu H, et al. (2014)."Tipepidine in adolescent patients with depression: a 4 week, open-label, preliminary study".Neuropsychiatric Disease and Treatment.10:719–722.doi:10.2147/NDT.S63075.PMC 4015794.PMID 24833905.
  8. ^Honda S, Kawaura K, Soeda F, Shirasaki T, Takahama K (January 2011). "The potent inhibitory effect of tipepidine on marble-burying behavior in mice".Behavioural Brain Research.216 (1):308–312.doi:10.1016/j.bbr.2010.08.010.PMID 20713091.S2CID 21118027.
  9. ^Sasaki T, Hashimoto K, Tachibana M, Kurata T, Okawada K, Ishikawa M, et al. (2014)."Tipepidine in children with attention deficit/hyperactivity disorder: a 4-week, open-label, preliminary study".Neuropsychiatric Disease and Treatment.10:147–151.doi:10.2147/NDT.S58480.PMC 3908907.PMID 24493927.
  10. ^Hashimoto K, Sasaki T (February 2015). "Old drug tipepidine as new hope for children with ADHD".The Australian and New Zealand Journal of Psychiatry.49 (2):181–182.doi:10.1177/0004867414553952.PMID 25280911.S2CID 8496750.
  11. ^Dehbozorghi S, Bagheri S, Moradi K, Shokraee K, Mohammadi MR, Akhondzadeh S (November 2019)."Efficacy and safety of tipepidine as adjunctive therapy in children with attention-deficit/hyperactivity disorder: Randomized, double-blind, placebo-controlled clinical trial".Psychiatry and Clinical Neurosciences.73 (11):690–696.doi:10.1111/pcn.12913.PMID 31294924.S2CID 195879810.
  12. ^Hamasaki R, Shirasaki T, Soeda F, Takahama K (November 2013). "Tipepidine activates VTA dopamine neuron via inhibiting dopamine D₂ receptor-mediated inward rectifying K⁺ current".Neuroscience.252:24–34.doi:10.1016/j.neuroscience.2013.07.044.PMID 23896570.S2CID 207253362.
  13. ^Hamao K, Kawaura K, Soeda F, Hamasaki R, Shirasaki T, Takahama K (May 2015). "Tipepidine increases dopamine level in the nucleus accumbens without methamphetamine-like behavioral sensitization".Behavioural Brain Research.284:118–124.doi:10.1016/j.bbr.2015.02.012.PMID 25687844.S2CID 22324207.
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