Clobutinol: Difference between revisions

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{{drugbox
{{Drugbox
| IUPAC_name       = 1-(4-chlorophenyl)-4-dimethylamino-2,3-dimethyl-butan-2-ol
| Verifiedfields = changed
| image             = clobutinol.png
| Watchedfields = changed
| CAS_number        = 14860-49-2
| verifiedrevid = 447812939
| ATC_prefix        = R05
| IUPAC_name = (''RS'')-1-(4-chlorophenyl)-4-dimethylamino-2,3-dimethyl-butan-2-ol
| ATC_suffix        = DB03
| image = clobutinol.png
| PubChem          = 26937
| width = 240
| DrugBank          =
| imagename = 1 : 1 mixture (racemate)
| C=14|H=22|Cl=1|N=1|O=1
| drug_name = Clobutinol
| molecular_weight  = 255.783 g/mol
 
| bioavailability  =
<!--Clinical data-->
| protein_bound    =
| tradename =
| metabolism        =
| Drugs.com = {{drugs.com|international|clobutinol}}
| elimination_half-life =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| excretion        =
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_category =   
| pregnancy_US     = <!-- A / B            / C / D / X -->
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| pregnancy_category=   
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_status = Withdrawn
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
<sub>(EU)</sub>| routes_of_administration = oral
| legal_status     =  
 
| routes_of_administration =  
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 14860-49-2
| ATC_prefix = R05
| ATC_suffix = DB03
| PubChem = 26937
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1474889
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank = DB09004
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 25085
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1NY2IX043A
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07716
 
<!--Chemical data-->
| 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
| 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 = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KVHHQGIIZCJATJ-UHFFFAOYSA-N
}}
}}


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==Side effects and withdrawal==
==Side effects and withdrawal==
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 pmid | 15280442 }}</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
}}</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>. 
[[Boehringer Ingelheim]] products containing clobutinol were voluntarily withdrawn from sale in [[Germany]], and the rest of the world, on August 31, 2007.<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.
}}</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>
The approval for Germany and the EU was revoked in 2008.<ref>
<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>.
{{ cite web
| 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
}}</ref>


==See also==
==See also==
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==References==
==References==
<references/>
{{reflist}}
 
{{pharmacology-stub}}


{{Cough and cold preparations}}
{{Cough and cold preparations}}
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[[Category:Organochlorides]]
[[Category:Organochlorides]]
[[Category:Amines]]
[[Category:Amines]]
[[Category:Alcohols]]


[[de:Clobutinol]]
{{respiratory-system-drug-stub}}
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Revision as of 17:25, 6 April 2015

Clobutinol
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		oral
ATC code
Legal status
Legal status
  • Withdrawn
(EU)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
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
FormulaC14H22ClNO
Molar mass255.783 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Clobutinol is a cough suppressant distributed by Boehringer-Ingelheim, Novartis's Hexal (Sandoz), Stada and possibly other companies.

Side effects and withdrawal

Studies in 2004 had indicated that clobutinol has the potential to prolong the QT interval.[1] Clobutinol was in 2007 determined to cause cardiac arrhythmia in some patients.[2]

Boehringer Ingelheim products containing clobutinol were voluntarily withdrawn from sale in Germany, and the rest of the world, on August 31, 2007.[3]

The approval for Germany and the EU was revoked in 2008.[4]

See also

References

  1. ↑ PMID 15280442 (PMID 15280442)
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  2. ↑ "Clobutinol-haltige Arzneimittel: BfArM ordnet Widerruf der Zulassung an". BfArM (German Federal Institute for Drugs and Medical Devices). 2007-08-31. Clobutinol: BfArM orders cancellation of approval
  3. ↑ "Boehringer Ingelheim voluntarily withdraws its clobutinol containing medications". Boehringer Ingelheim. 2007-08-31.
  4. ↑ "Cancellation of approval" (pdf). BfArM (German Federal Institute for Drugs and Medical Devices). 2008-06-06. Die Zulassungen für die o.g. Arzneimittel werden mit sofortiger Wirkung widerrufen.

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