Clobutinol: Difference between revisions

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Updating {{drugbox}} (changes to watched fields - added verified revid - updated 'ChEMBL_Ref', 'ChEBI_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|b
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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 444368202
| verifiedrevid = 447812939
| IUPAC_name = (''RS'')-1-(4-chlorophenyl)- 4-dimethylamino- 2,3-dimethyl- butan- 2-ol
| IUPAC_name = (''RS'')-1-(4-chlorophenyl)-4-dimethylamino-2,3-dimethyl-butan-2-ol
| image = clobutinol.png
| image = clobutinol.png
| width = 240
| width = 240
| imagename = 1 : 1 mixture (racemate)
| chirality = [[Racemic mixture]]
| drug_name = Clobutinol

<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename = Biotussin, Lomisat, Pertoxil, Silomat
| Drugs.com = {{drugs.com|international|clobutinol}}
| Drugs.com = {{drugs.com|international|clobutinol}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
Line 18: Line 18:
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status =
| legal_status = Withdrawn
| routes_of_administration =
<sub>(EU)</sub>| routes_of_administration = oral


<!--Pharmacokinetic data-->
<!--Pharmacokinetic data-->
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<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 14860-49-2
| CAS_number = 14860-49-2
| ATC_prefix = R05
| ATC_prefix = R05
| ATC_suffix = DB03
| ATC_suffix = DB03
| PubChem = 26937
| PubChem = 26937
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| DrugBank =
| ChEMBL = 1474889
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB09004
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25085
| ChemSpiderID = 25085
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<!--Chemical data-->
<!--Chemical data-->
| C=14 | H=22 | Cl=1 | N=1 | O=1
| C=14 | H=22 | Cl=1 | N=1 | O=1
| molecular_weight = 255.783 g/mol
| smiles = Clc1ccc(cc1)CC(O)(C)C(C)CN(C)C
| smiles = Clc1ccc(cc1)CC(O)(C)C(C)CN(C)C
| InChI = 1/C14H22ClNO/c1-11(10-16(3)4)14(2,17)9-12-5-7-13(15)8-6-12/h5-8,11,17H,9-10H2,1-4H3
| InChIKey = KVHHQGIIZCJATJ-UHFFFAOYAE
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H22ClNO/c1-11(10-16(3)4)14(2,17)9-12-5-7-13(15)8-6-12/h5-8,11,17H,9-10H2,1-4H3
| StdInChI = 1S/C14H22ClNO/c1-11(10-16(3)4)14(2,17)9-12-5-7-13(15)8-6-12/h5-8,11,17H,9-10H2,1-4H3
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}}
}}


'''Clobutinol''' is a [[cough suppressant]] distributed by [[Boehringer-Ingelheim]], [[Novartis]]'s Hexal ([[Sandoz]]), Stada and possibly other companies.
'''Clobutinol''' is a [[cough suppressant]] formerly distributed by [[Boehringer Ingelheim]] and its licensees under the names '''Lomisat''' and '''Silomat''', by Bioter as '''Biotussin''', and by Violani-Farmavigor as '''Pertoxil'''. It has been withdrawn from the market worldwide.


==Side effects and withdrawal==
==Side effects and withdrawal==
Side effects include drowsiness, dizziness, insomnia, nausea, vomiting, and abdominal discomfort.<ref>{{cite book |isbn=0-8103-7177-4 |title=Drugs Available Abroad, 1st Edition |page=29 |date=1991 | vauthors = Schlesser JL |publisher=Derwent Publications Ltd.}}</ref>
⚫
It was recently determined to cause [[cardiac arrhythmia]] in some patients.
⚫
Studies in 2004 had indicated that clobutinol has the potential to prolong the [[QT interval]].<ref name="pmid15280442">{{cite journal | vauthors = Bellocq C, Wilders R, Schott JJ, Louérat-Oriou B, Boisseau P, Le Marec H, Escande D, Baró I | display-authors = 6 | title = A common antitussive drug, clobutinol, precipitates the long QT syndrome 2 | journal = Molecular Pharmacology | volume = 66 | issue = 5 | pages = 1093–102 | date = November 2004 | pmid = 15280442 | doi = 10.1124/mol.104.001065 | s2cid = 12883606 }}</ref>
⚫
Clobutinol was in 2007 determined to cause [[cardiac arrhythmia]] in some patients.<ref>
{{ cite web
| url = http://www.bfarm.de/DE/BfArM/Presse/mitteil2007/pm20-2007.html
| title = Clobutinol-haltige Arzneimittel: BfArM ordnet Widerruf der Zulassung an.
| publisher = BfArM (German Federal Institute for Drugs and Medical Devices)
| date = 2007-08-31
| quote = Clobutinol: BfArM orders cancellation of approval
| url-status = dead
| archive-url = https://web.archive.org/web/20120401035256/http://www.bfarm.de/DE/BfArM/Presse/mitteil2007/pm20-2007.html
| archive-date = 2012-04-01
}}</ref>


⚫
[[Boehringer Ingelheim]] products containing clobutinol were voluntarily withdrawn from sale in [[Germany]], and the rest of the world, on August 31, 2007.<ref>
⚫
Recent studies have indicated that clobutinol has the potential to prolong the [[QT interval]].<ref name="pmid15280442">{{cite journal |author=Bellocq C, Wilders R, Schott JJ, ''et al.'' |title=A common antitussive drug, clobutinol, precipitates the long QT syndrome 2 |journal=Mol. Pharmacol. |volume=66 |issue=5 |pages=1093–102 |year=2004 |pmid=15280442 |doi=10.1124/mol.104.001065}}</ref><ref>Expert statement on BfArM website: ''[http://www.bfarm.de/cln_042/nn_828832/DE/Pharmakovigilanz/stufenplanverf/stp-clobutinol.html__nnn=true]''. Retrieved 2007-SEP-01.</ref>.
{{ cite web
| url = http://www.boehringer-ingelheim.com/news/news_releases/press_releases/2007/31_august_2007.html
| publisher = Boehringer Ingelheim
| date = 2007-08-31
| title = Boehringer Ingelheim voluntarily withdraws its clobutinol containing medications.
| url-status = dead
| archive-url = https://web.archive.org/web/20120127070831/http://www.boehringer-ingelheim.com/news/news_releases/press_releases/2007/31_august_2007.html
| archive-date = 2012-01-27
}}</ref>


The approval for Germany and the EU was revoked in 2008.<ref>
⚫
[[Boehringer Ingelheim]] products containing clobutinol were withdrawn from sale in [[Germany]], and the rest of the world, on August 31, 2007<ref>Yahoo! News: ''[http://de.news.yahoo.com/dpa/20070831/tsc-bundesinstitut-ruft-hustenmittel-zur-99e13cf_1.html Bundesinstitut ruft Hustenmittel zurück]'' [in German]. Retrieved 2007-AUG-31.</ref>
{{ cite web
<ref>tagesschau.de: ''[http://www.tagesschau.de/aktuell/meldungen/0,,OID7387590_REF1,00.html Bundesinstitut verbietet Hustenmittel Clobutinol]'' [in German]. Retrieved 2007-AUG-31.</ref><ref>Company Website:''[http://www.boehringer-ingelheim.com/corporate/asp/news/ndetail.asp?ID=4854 Boehringer Ingelheim voluntarily withdraws its clobutinol containing medications]'' [English]. Retrieved 2007-Sep-01.</ref>.
| title = Cancellation of approval
| url = http://www.bfarm.de/SharedDocs/1_Downloads/DE/Pharmakovigilanz/stufenplverf/globutinol_bescheid_080613.pdf?__blob=publicationFile
| format = pdf
| quote = Die Zulassungen für die o.g. Arzneimittel werden mit sofortiger Wirkung widerrufen.
| publisher = BfArM (German Federal Institute for Drugs and Medical Devices)
| date = 2008-06-06
| url-status = dead
| archive-url = https://web.archive.org/web/20120401034947/http://www.bfarm.de/SharedDocs/1_Downloads/DE/Pharmakovigilanz/stufenplverf/globutinol_bescheid_080613.pdf?__blob=publicationFile
| archive-date = 2012-04-01
}}</ref>


Prior to withdrawal, it was available throughout Europe and Central America, as well as in South Africa. Trade names include Biotussin, Lomisat (Spain), Pertoxil (Italy), and in most of the world, Silomat.<ref>{{cite book |isbn=0-8103-7177-4 |title=Drugs Available Abroad, 1st Edition |page=29 |date=1991 | vauthors = Schlesser JL |publisher=Derwent Publications Ltd.}}</ref>
==See also==
== See also ==
* [[QT interval]]
* [[QT interval]]
* [[Long QT syndrome]]
* [[Long QT syndrome]]


==References==
== References ==
{{reflist}}
<references/>


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


[[Category:Antitussives]]
[[Category:Antitussives]]
[[Category:Organochlorides]]
[[Category:Chloroarenes]]
[[Category:Amines]]
[[Category:Dimethylamino compounds]]
[[Category:Alcohols]]
[[Category:Tertiary alcohols]]




{{respiratory-system-drug-stub}}
{{respiratory-system-drug-stub}}

[[de:Clobutinol]]
[[fa:کلوبوتینول]]
[[fr:Clobutinol]]
[[nl:Clobutinol]]
[[pt:Clobutinol]]
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