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Legal status	Withdrawn (EU)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
ECHA InfoCard	100.035.373
Chemical and physical data
Formula	C14H22ClNO
Molar mass	255.783 g/mol
3D model (Jmol)	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
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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Boehringer Ingelheim products containing clobutinol were voluntarily withdrawn from sale in Germany, and the rest of the world, on August 31, 2007.^[3]

The approval for Germany and the EU was revoked in 2008.^[4]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

• QT interval
• Long QT syndrome

References

1. Bellocq, C.; Wilders, R.; Schott, J. J.; Louérat-Oriou, B.; Boisseau, P.; Le Marec, H.; Escande, D.; Baró, I. (2004). "A Common Antitussive Drug, Clobutinol, Precipitates the Long QT Syndrome 2". Molecular Pharmacology. 66 (5): 1093–1102. 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. 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.