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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  =
| protein_bound    =
| metabolism        =
| elimination_half-life =  
| excretion        =
| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US      =  <!-- A / B            / C / D / X -->
| pregnancy_category= 
| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA          =  <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK          =  <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US          =  <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status      =
| routes_of_administration =
}}


'''Clobutinol''' is a [[cough suppressant]] distributed by [[Boehringer-Ingelheim]], [[Novartis]]'s Hexal ([[Sandoz]]), Stada and possibly other companies.
<!--Clinical data-->
| tradename = 
| Drugs.com = {{drugs.com|international|clobutinol}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| legal_status =  Withdrawn
<sub>(EU)</sub>| routes_of_administration =  oral


==Side effects and withdrawal==
<!--Pharmacokinetic data-->
It was recently determined to cause [[cardiac arrhythmia]] in some patients.
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion = 


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>. 
<!--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


[[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>
<!--Chemical data-->
<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>.
| 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
}}
__NOTOC__
{{SI}}
{{CMG}}
==Overview==
'''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]].
Clobutinol was in 2007 determined to cause [[cardiac arrhythmia]] in some patients.
[[Boehringer Ingelheim]] products containing clobutinol were voluntarily withdrawn from sale in [[Germany]], and the rest of the world, on August 31, 2007.
The approval for Germany and the EU was revoked in 2008.
==See also==
==See also==
* [[QT interval]]
* [[QT interval]]
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==References==
==References==
<references/>
{{reflist|2}}
 
{{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]]
[[Category:Drug]]
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Latest revision as of 19:33, 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)

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

Overview

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. Clobutinol was in 2007 determined to cause cardiac arrhythmia in some patients. Boehringer Ingelheim products containing clobutinol were voluntarily withdrawn from sale in Germany, and the rest of the world, on August 31, 2007. The approval for Germany and the EU was revoked in 2008.

See also

References

Template:Cough and cold preparations