Tipepidine

Tipepidine
	File:Tipepidine.svg
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	R05DB24 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) ;
Identifiers
	IUPAC name 3-(di-2-thienylmethylene)-1-methylpiperidine;
CAS Number	5169-78-8 ;
PubChem CID	5484;
ChemSpider	5284 ;
UNII	2260ZP67IT;
KEGG	D08604 ;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C15H17NS2
Molar mass	275.434 g/mol
3D model (JSmol)	Interactive image;
	SMILES s1cccc1/C(c2sccc2)=C3\CCCN(C)C3;
	InChI 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 ; Key:JWIXXNLOKOAAQT-UHFFFAOYSA-N ;
(verify)

Tipepidine (INN) (brand names Asverin, Antupex, Asvelik, Asvex, Bitiodin, Cofdenin A, Hustel, Nodal, Sotal), also known as tipepidine hibenzate (JAN), is a synthetic, non-opioid antitussive and expectorant of the thiambutene class.^[1]^[2] It acts as an inhibitor of G protein-coupled inwardly-rectifying potassium channels (GIRKs).^[3] The drug was discovered in the 1950s,^[4] and was developed in Japan in 1959.^[5] It is used as the hibenzate and citrate salts.^[1]^[5]

The usual dose is 20 mg every 4–6 hours.^{[citation needed]} Possible side effects of tipepidine, especially in overdose, may include drowsiness, vertigo, delirium, disorientation, loss of consciousness, and confusion.^[5]

Tipepidine has recently garnered interest as a potential psychiatric drug. It is being investigated in depression,^[3]^[6]^[7] obsessive-compulsive disorder,^[8] and attention-deficit hyperactivity disorder (ADHD).^[9]^[10] Through inhibition of GIRK channels, tipepidine increases dopamine levels in the nucleus accumbens, but without increasing locomotor activity or producing methamphetamine-like behavioral sensitization, and this action appears to be at least partly responsible for its antidepressant-like effects in rodents.^[11]^[12]

References

↑ ^1.0 ^1.1 C.R. Ganellin; David J. Triggle (21 November 1996). Dictionary of Pharmacological Agents. CRC Press. pp. 1988–. ISBN 978-0-412-46630-4.
↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1649–. ISBN 978-3-88763-075-1.
↑ ^3.0 ^3.1 Kawaura, Kazuaki; Ogata, Yukino; Inoue, Masako; Honda, Sokichi; Soeda, Fumio; Shirasaki, Tetsuya; Takahama, Kazuo (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. ISSN 0166-4328.
↑ ES Patent 272195
↑ ^5.0 ^5.1 ^5.2 Imai, Yuki; Ishii, Wakako; Endo, Ayumi; Arakawa, Chikako; Kohira, Ryutaro; Fujita, Yukihiko; Fuchigami, Tatsuo; Mugishima, Hideo (2011). "Tipepidine hibenzate intoxication". Pediatrics International. 53 (5): 779–781. doi:10.1111/j.1442-200X.2010.03297.x. ISSN 1328-8067.
↑ KAWAURA, Kazuaki; HONDA, Sokichi; SOEDA, Fumio; SHIRASAKI, Tetsuya; TAKAHAMA, Kazuo (2010). "A 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. ISSN 0031-6903.
↑ 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". Neuropsychiatr Dis Treat. 10: 719–22. doi:10.2147/NDT.S63075. PMC 4015794. PMID 24833905.
↑ Honda, Sokichi; Kawaura, Kazuaki; Soeda, Fumio; Shirasaki, Tetsuya; Takahama, Kazuo (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. ISSN 0166-4328.
↑ 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". Neuropsychiatr Dis Treat. 10: 147–51. doi:10.2147/NDT.S58480. PMC 3908907. PMID 24493927.
↑ Hashimoto, K.; Sasaki, T. (2014). "Old drug tipepidine as new hope for children with ADHD". Australian & New Zealand Journal of Psychiatry. 49 (2): 181–182. doi:10.1177/0004867414553952. ISSN 0004-8674.
↑ Hamasaki R, Shirasaki T, Soeda F, Takahama K (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.
↑ Hamao K, Kawaura K, Soeda F, Hamasaki R, Shirasaki T, Takahama K (2015). "Tipepidine increases dopamine level in the nucleus accumbens without methamphetamine-like behavioral sensitization". Behav. Brain Res. doi:10.1016/j.bbr.2015.02.012. PMID 25687844.

Template:Cough and cold preparations

Template:Respiratory-system-drug-stub Template:Nervous-system-drug-stub

[GanellinTriggle1996-1] 1.0 ^1.1 C.R. Ganellin; David J. Triggle (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.

[KawauraOgata2009-3] 3.0 ^3.1 Kawaura, Kazuaki; Ogata, Yukino; Inoue, Masako; Honda, Sokichi; Soeda, Fumio; Shirasaki, Tetsuya; Takahama, Kazuo (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. ISSN 0166-4328.

[4] ES Patent 272195

[ImaiIshii2011-5] 5.0 ^5.1 ^5.2 Imai, Yuki; Ishii, Wakako; Endo, Ayumi; Arakawa, Chikako; Kohira, Ryutaro; Fujita, Yukihiko; Fuchigami, Tatsuo; Mugishima, Hideo (2011). "Tipepidine hibenzate intoxication". Pediatrics International. 53 (5): 779–781. doi:10.1111/j.1442-200X.2010.03297.x. ISSN 1328-8067.

[KAWAURAHONDA2010-6] KAWAURA, Kazuaki; HONDA, Sokichi; SOEDA, Fumio; SHIRASAKI, Tetsuya; TAKAHAMA, Kazuo (2010). "A 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. ISSN 0031-6903.

[pmid24833905-7] 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". Neuropsychiatr Dis Treat. 10: 719–22. doi:10.2147/NDT.S63075. PMC 4015794. PMID 24833905.

[HondaKawaura2011-8] Honda, Sokichi; Kawaura, Kazuaki; Soeda, Fumio; Shirasaki, Tetsuya; Takahama, Kazuo (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. ISSN 0166-4328.

[pmid24493927-9] 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". Neuropsychiatr Dis Treat. 10: 147–51. doi:10.2147/NDT.S58480. PMC 3908907. PMID 24493927.

[HashimotoSasaki2014-10] Hashimoto, K.; Sasaki, T. (2014). "Old drug tipepidine as new hope for children with ADHD". Australian & New Zealand Journal of Psychiatry. 49 (2): 181–182. doi:10.1177/0004867414553952. ISSN 0004-8674.

[pmid23896570-11] Hamasaki R, Shirasaki T, Soeda F, Takahama K (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.

[pmid25687844-12] Hamao K, Kawaura K, Soeda F, Hamasaki R, Shirasaki T, Takahama K (2015). "Tipepidine increases dopamine level in the nucleus accumbens without methamphetamine-like behavioral sensitization". Behav. Brain Res. doi:10.1016/j.bbr.2015.02.012. PMID 25687844.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

Tipepidine

See also

References

Navigation menu