Clobutinol

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

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Legal status	Withdrawn (EU)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Boehringer Ingelheim products containing clobutinol were voluntarily withdrawn from sale in Germany, and the rest of the world, on August 31, 2007.[3]

The approval for Germany and the EU was revoked in 2008.[4]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