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Details

Stereochemistry UNKNOWN
Molecular Formula C14H22ClNO
Molecular Weight 255.784
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOBUTINOL

SMILES

CC(CN(C)C)C(C)(O)CC1=CC=C(Cl)C=C1

InChI

InChIKey=KVHHQGIIZCJATJ-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H22ClNO
Molecular Weight 255.784
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Clobutinol is a cough suppressant that is withdrawn from the US and EU markets. Clobutinol was used for the short-term treatment of irritable, non-productive cough (a ‘dry' cough where the patient does not cough up any phlegm or mucus). Medicines containing clobutinol have been available since 1961 and were authorised in a number of Member States. Clobutinol-containing medicines were available in Austria, Belgium, the Czech Republic, Germany, Greece, Finland and France. They include tablets, oral solutions, syrups and solutions for injection, and were available over-the-counter in many Member States. Clobutinol was available as generic and branded medicines, most of which were marketed by Boehringer Ingelheim under the trade name Silomat. Studies in 2004 had indicated that clobutinol has the potential to prolong the QT interval. In 2007, Clobutinol was determined to cause cardiac arrhythmia in some patients.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.9 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Silomat

PubMed

Sample Use Guides

In Vivo Use Guide
Oral use. .Adults only: -Usual dose: 1 - 2 tablets/dose, to be repeated after 8 hs if needed. -Maximum daily dose: do not exceed 6 tablets per day (ie, 240 mg). -Treatment duration: symptomatic treatment should be short (a few days) and limited to coughing crisis.
Route of Administration: Oral
In Vitro Use Guide
In isolated guinea pig ventricular tissues, clobutinol (3 uM) prolonged the action potential duration without affecting maximum upstroke velocity, but no further prolongation was observed after application of 30 uM clobutinol.
Substance Class Chemical
Record UNII
1NY2IX043A
Record Status Validated (UNII)
Record Version