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Legal status	Withdrawn; (EU)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 ;
CompTox Dashboard (EPA)	DTXSID2022838 ;
ECHA InfoCard	100.035.373
Chemical and physical data
Formula	C14H22ClNO
Molar mass	255.79 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	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 ;
	(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Boehringer Ingelheim products containing clobutinol were voluntarily withdrawn from sale in Germany, and the rest of the world, on August 31, 2007.^[3]

The approval for Germany and the EU was revoked in 2008.^[4]

References

^ Bellocq C, Wilders R, Schott JJ, Louérat-Oriou B, Boisseau P, Le Marec H, et al. (November 2004). "A common antitussive drug, clobutinol, precipitates the long QT syndrome 2". Molecular Pharmacology. 66 (5): 1093–102. doi:10.1124/mol.104.001065. PMID 15280442.
^ "Clobutinol-haltige Arzneimittel: BfArM ordnet Widerruf der Zulassung an". BfArM (German Federal Institute for Drugs and Medical Devices). 2007-08-31. Archived from the original on 2012-04-01. Clobutinol: BfArM orders cancellation of approval
^ "Boehringer Ingelheim voluntarily withdraws its clobutinol containing medications". Boehringer Ingelheim. 2007-08-31. Archived from the original on 2012-01-27.
^ "Cancellation of approval" (PDF). BfArM (German Federal Institute for Drugs and Medical Devices). 2008-06-06. Archived from the original (pdf) on 2012-04-01. Die Zulassungen für die o.g. Arzneimittel werden mit sofortiger Wirkung widerrufen.

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[pmid15280442-1] Bellocq C, Wilders R, Schott JJ, Louérat-Oriou B, Boisseau P, Le Marec H, et al. (November 2004). "A common antitussive drug, clobutinol, precipitates the long QT syndrome 2". Molecular Pharmacology. 66 (5): 1093–102. doi:10.1124/mol.104.001065. PMID 15280442.

[2] "Clobutinol-haltige Arzneimittel: BfArM ordnet Widerruf der Zulassung an". BfArM (German Federal Institute for Drugs and Medical Devices). 2007-08-31. Archived from the original on 2012-04-01. Clobutinol: BfArM orders cancellation of approval

[3] "Boehringer Ingelheim voluntarily withdraws its clobutinol containing medications". Boehringer Ingelheim. 2007-08-31. Archived from the original on 2012-01-27.

[4] "Cancellation of approval" (PDF). BfArM (German Federal Institute for Drugs and Medical Devices). 2008-06-06. Archived from the original (pdf) on 2012-04-01. Die Zulassungen für die o.g. Arzneimittel werden mit sofortiger Wirkung widerrufen.

[1]

[2]

[3]

[4]

Side effects and withdrawal

See also

References