Clobutinol: Difference between revisions

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List of terms related to Clobutinol

Clobutinol
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	oral
ATC code	R05DB03 (WHO) ;
Legal status
Legal status	Withdrawn; (EU)
Identifiers
	IUPAC name (RS)-1-(4-chlorophenyl)-4-dimethylamino-2,3-dimethyl-butan-2-ol;
CAS Number	14860-49-2 ;
PubChem CID	26937;
DrugBank	DB09004 ;
ChemSpider	25085 ;
UNII	1NY2IX043A;
KEGG	D07716 ;
ChEMBL	ChEMBL1474889 ;
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	C14H22ClNO
Molar mass	255.783 g/mol
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)CC(O)(C)C(C)CN(C)C;
	InChI InChI=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 ; Key:KVHHQGIIZCJATJ-UHFFFAOYSA-N ;
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VisualWikitext

Latest revision as of 19:33, 6 April 2015

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 Boehringer Ingelheim products containing clobutinol were voluntarily withdrawn from sale in Germany, and the rest of the world, on August 31, 2007. The approval for Germany and the EU was revoked in 2008.

References

Template:Cough and cold preparations

@@ Line 1: / Line 1: @@
-{{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==
 * [[QT interval]]
@@ Line 40: / Line 73: @@
 ==References==
-<references/>
+{{reflist|2}}
-{{pharmacology-stub}}
 {{Cough and cold preparations}}
@@ Line 49: / Line 80: @@
 [[Category:Organochlorides]]
 [[Category:Amines]]
+[[Category:Alcohols]]
-[[de:Clobutinol]]
+[[Category:Drug]]
-{{WikiDoc Help Menu}}

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	oral
ATC code	R05DB03 (WHO)
Legal status
Legal status	Withdrawn _(EU)
Identifiers
IUPAC name (RS)-1-(4-chlorophenyl)-4-dimethylamino-2,3-dimethyl-butan-2-ol
CAS Number	14860-49-2^Y
PubChem CID	26937
DrugBank	DB09004^N
ChemSpider	25085^Y
UNII	1NY2IX043A
KEGG	D07716^Y
ChEMBL	ChEMBL1474889^N
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	C₁₄H₂₂ClNO
Molar mass	255.783 g/mol
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1)CC(O)(C)C(C)CN(C)C
InChI InChI=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^Y Key:KVHHQGIIZCJATJ-UHFFFAOYSA-N^Y
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Clobutinol: Difference between revisions

Latest revision as of 19:33, 6 April 2015

Overview

Side effects and withdrawal

See also

References

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