Tipepidine

	WikiDoc Resources for Tipepidine
Articles
Most recent articles on Tipepidine Most cited articles on Tipepidine Review articles on Tipepidine Articles on Tipepidine in N Eng J Med, Lancet, BMJ
Media
Powerpoint slides on Tipepidine Images of Tipepidine Photos of Tipepidine Podcasts & MP3s on Tipepidine Videos on Tipepidine
Evidence Based Medicine
Cochrane Collaboration on Tipepidine Bandolier on Tipepidine TRIP on Tipepidine
Clinical Trials
Ongoing Trials on Tipepidine at Clinical Trials.gov Trial results on Tipepidine Clinical Trials on Tipepidine at Google
Guidelines / Policies / Govt
US National Guidelines Clearinghouse on Tipepidine NICE Guidance on Tipepidine NHS PRODIGY Guidance FDA on Tipepidine CDC on Tipepidine
Books
Books on Tipepidine
News
Tipepidine in the news Be alerted to news on Tipepidine News trends on Tipepidine
Commentary
Blogs on Tipepidine
Definitions
Definitions of Tipepidine
Patient Resources / Community
Patient resources on Tipepidine Discussion groups on Tipepidine Patient Handouts on Tipepidine Directions to Hospitals Treating Tipepidine Risk calculators and risk factors for Tipepidine
Healthcare Provider Resources
Symptoms of Tipepidine Causes & Risk Factors for Tipepidine Diagnostic studies for Tipepidine Treatment of Tipepidine
Continuing Medical Education (CME)
CME Programs on Tipepidine
International
Tipepidine en Espanol Tipepidine en Francais
Business
Tipepidine in the Marketplace Patents on Tipepidine
Experimental / Informatics
List of terms related to Tipepidine

Tipepidine
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)

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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

[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

Overview

See also

References

Navigation menu

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^Y
PubChem CID	5484
ChemSpider	5284^Y
UNII	2260ZP67IT
KEGG	D08604^Y
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^Y Key:JWIXXNLOKOAAQT-UHFFFAOYSA-N^Y
(verify)