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{{drugbox
{{Drugbox
| IUPAC_name       = 3-(dithiophen-2-ylmethylidene)-1-methyl-piperidine
| verifiedrevid = 447810095
| image             = Tipepidine.svg
| IUPAC_name = 3-(di-2-thienylmethylene)-1-methylpiperidine
| CAS_number        =
| image = Tipepidine.png
| ATC_prefix        = R05
 
| ATC_suffix        = DB24
<!--Clinical data-->
| PubChem          = 5484
| tradename =
| DrugBank          =
| Drugs.com = {{drugs.com|international|tipepidine}}
| C = 15 | H = 17 | N = 1 | S = 2
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| molecular_weight  = 275.434 g/mol
| pregnancy_US = <!-- A / B            / C / D / X -->
| bioavailability  =
| pregnancy_category =   
| protein_bound    =
| legal_AU = S4
| metabolism        =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| elimination_half-life =
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| excretion        =
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_status =
| pregnancy_US     = <!-- A / B            / C / D / X -->
| routes_of_administration = Oral
| pregnancy_category=   
 
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
<!--Pharmacokinetic data-->
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| bioavailability = 
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| protein_bound = 
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| metabolism = 
| legal_status     =  
| elimination_half-life = 
| routes_of_administration =  
| excretion = 
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 5169-78-8
| ATC_prefix = R05
| ATC_suffix = DB24
| PubChem = 5484
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5284
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2260ZP67IT
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D08604
 
<!--Chemical data-->
| C=15 | H=17 | N=1 | S=2
| molecular_weight = 275.434 g/mol
| smiles = s1cccc1/C(c2sccc2)=C3\CCCN(C)C3
| InChI = 1/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
| InChIKey = JWIXXNLOKOAAQT-UHFFFAOYAP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JWIXXNLOKOAAQT-UHFFFAOYSA-N
}}
}}
'''Tipepidine''' is a [[cough suppressant]].
                    __NOTOC__
{{SI}}
{{CMG}}
 
==Overview==
'''Tipepidine''' ([[International Nonproprietary Name|INN]]) (brand names '''Asverin''', '''Antupex''', '''Asvelik''', '''Asvex''', '''Bitiodin''', '''Cofdenin A''', '''Hustel''', '''Nodal''', '''Sotal'''), also known as '''tipepidine hibenzate''' ([[Japanese Accepted Name|JAN]]), is a [[Organic compound#Synthetic compounds|synthetic]], non-[[opioid]] [[antitussive]] and [[expectorant]] of the [[thiambutene]] class.<ref name="GanellinTriggle1996">{{cite book|author1=C.R. Ganellin|author2=David J. Triggle|title=Dictionary of Pharmacological Agents|url=http://books.google.com/books?id=A0THacd46ZsC&pg=PA1988|date=21 November 1996|publisher=CRC Press|isbn=978-0-412-46630-4|pages=1988–}}</ref><ref>{{cite book|title=Index Nominum 2000: International Drug Directory|url=http://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1649|date=January 2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=1649–}}</ref> It acts as an [[channel blocker|inhibitor]] of [[G protein-coupled inwardly-rectifying potassium channel]]s (GIRKs).<ref name="KawauraOgata2009">{{cite journal|last1=Kawaura|first1=Kazuaki|last2=Ogata|first2=Yukino|last3=Inoue|first3=Masako|last4=Honda|first4=Sokichi|last5=Soeda|first5=Fumio|last6=Shirasaki|first6=Tetsuya|last7=Takahama|first7=Kazuo|title=The centrally acting non-narcotic antitussive tipepidine produces antidepressant-like effect in the forced swimming test in rats|journal=Behavioural Brain Research|volume=205|issue=1|year=2009|pages=315–318|issn=01664328|doi=10.1016/j.bbr.2009.07.004}}</ref> The drug was discovered in the 1950s,<ref>ES Patent 272195</ref> and was developed in [[Japan]] in 1959.<ref name="ImaiIshii2011">{{cite journal|last1=Imai|first1=Yuki|last2=Ishii|first2=Wakako|last3=Endo|first3=Ayumi|last4=Arakawa|first4=Chikako|last5=Kohira|first5=Ryutaro|last6=Fujita|first6=Yukihiko|last7=Fuchigami|first7=Tatsuo|last8=Mugishima|first8=Hideo|title=Tipepidine hibenzate intoxication|journal=Pediatrics International|volume=53|issue=5|year=2011|pages=779–781|issn=13288067|doi=10.1111/j.1442-200X.2010.03297.x}}</ref> It is used as the [[hibenzate]] and [[citrate]] salts.<ref name="GanellinTriggle1996" /><ref name="ImaiIshii2011" />
The usual dose is 20&nbsp;mg every 4&ndash;6 hours.{{Citation needed|date=February 2015}} Possible [[side effect]]s of tipepidine, especially in [[overdose]], may include [[drowsiness]], [[vertigo]], [[delirium]], [[disorientation]], [[loss of consciousness]], and [[confusion]].<ref name="ImaiIshii2011" />
 
Tipepidine has recently garnered interest as a potential [[psychiatric drug]]. It is being investigated in [[major depressive disorder|depression]],<ref name="KawauraOgata2009" /><ref name="KAWAURAHONDA2010">{{cite journal|last1=KAWAURA|first1=Kazuaki|last2=HONDA|first2=Sokichi|last3=SOEDA|first3=Fumio|last4=SHIRASAKI|first4=Tetsuya|last5=TAKAHAMA|first5=Kazuo|title=A Novel Antidepressant-like Action of Drugs Possessing GIRK Channel Blocking Action in Rats|journal=YAKUGAKU ZASSHI|volume=130|issue=5|year=2010|pages=699–705|issn=0031-6903|doi=10.1248/yakushi.130.699}}</ref><ref name="pmid24833905">{{vcite2 journal | vauthors = Sasaki T, Hashimoto K, Tachibana M, Kurata T, Kimura H, Komatsu H, Ishikawa M, Hasegawa T, Shiina A, Hashimoto T, Kanahara N, Shiraishi T, Iyo M | title = Tipepidine in adolescent patients with depression: a 4 week, open-label, preliminary study | journal = Neuropsychiatr Dis Treat | volume = 10 | issue = | pages = 719–22 | year = 2014 | pmid = 24833905 | pmc = 4015794 | doi = 10.2147/NDT.S63075 | url = }}</ref> [[obsessive-compulsive disorder]],<ref name="HondaKawaura2011">{{cite journal|last1=Honda|first1=Sokichi|last2=Kawaura|first2=Kazuaki|last3=Soeda|first3=Fumio|last4=Shirasaki|first4=Tetsuya|last5=Takahama|first5=Kazuo|title=The potent inhibitory effect of tipepidine on marble-burying behavior in mice|journal=Behavioural Brain Research|volume=216|issue=1|year=2011|pages=308–312|issn=01664328|doi=10.1016/j.bbr.2010.08.010}}</ref> and [[attention-deficit hyperactivity disorder]] (ADHD).<ref name="pmid24493927">{{vcite2 journal | vauthors = Sasaki T, Hashimoto K, Tachibana M, Kurata T, Okawada K, Ishikawa M, Kimura H, Komatsu H, Ishikawa M, Hasegawa T, Shiina A, Hashimoto T, Kanahara N, Shiraishi T, Iyo M | title = Tipepidine in children with attention deficit/hyperactivity disorder: a 4-week, open-label, preliminary study | journal = Neuropsychiatr Dis Treat | volume = 10 | issue = | pages = 147–51 | year = 2014 | pmid = 24493927 | pmc = 3908907 | doi = 10.2147/NDT.S58480 | url = }}</ref><ref name="HashimotoSasaki2014">{{cite journal|last1=Hashimoto|first1=K.|last2=Sasaki|first2=T.|title=Old drug tipepidine as new hope for children with ADHD|journal=Australian & New Zealand Journal of Psychiatry|volume=49|issue=2|year=2014|pages=181–182|issn=0004-8674|doi=10.1177/0004867414553952}}</ref> Through inhibition of GIRK channels, tipepidine increases [[dopamine]] levels in the [[nucleus accumbens]], but without increasing [[hyperactivity|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.<ref name="pmid23896570">{{vcite2 journal | vauthors = Hamasaki R, Shirasaki T, Soeda F, Takahama K | title = Tipepidine activates VTA dopamine neuron via inhibiting dopamine D₂ receptor-mediated inward rectifying K⁺ current | journal = Neuroscience | volume = 252 | issue = | pages = 24–34 | year = 2013 | pmid = 23896570 | doi = 10.1016/j.neuroscience.2013.07.044 | url = }}</ref><ref name="pmid25687844">{{vcite2 journal | vauthors = Hamao K, Kawaura K, Soeda F, Hamasaki R, Shirasaki T, Takahama K | title = Tipepidine increases dopamine level in the nucleus accumbens without methamphetamine-like behavioral sensitization | journal = Behav. Brain Res. | volume = | issue = | pages = | year = 2015 | pmid = 25687844 | doi = 10.1016/j.bbr.2015.02.012 | url = }}</ref>
 
==See also==
* [[Guaifenesin]]


{{pharmacology-stub}}
==References==
{{Reflist|2}}




{{Cough and cold preparations}}
{{Cough and cold preparations}}


[[Category:Antitussives]]
[[Category:Antitussives]]
{{WikiDoc Sources}}
[[Category:Drug]]
[[Category:Expectorants]]
[[Category:Thiophenes]]
[[Category:Piperidines]]

Latest revision as of 16:00, 9 April 2015

Tipepidine
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AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
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CAS Number
PubChem CID
ChemSpider
UNII
KEGG
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
FormulaC15H17NS2
Molar mass275.434 g/mol
3D model (JSmol)
  (verify)

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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]

See also

References

  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.
  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
  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.
  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.
  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.
  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.
  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.
  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.
  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.
  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.


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