CLOBUTINOL

Possibly Marketed Outside US

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 Search

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

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/referrals/Clobutinol/human_referral_000117.jsp
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB09004 and https://www.bfarm.de/SharedDocs/Downloads/DE/Arzneimittel/Pharmakovigilanz/Risikoinformationen/RisikoBewVerf/a-f/Clobutinol/expert_statement.pdf?__blob=publicationFile&v=3

Clobutinol is a cough suppressant that is withdrawn from the US and EU markets.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 Target	Pharmacology	Condition	Potency
HERG 99 Target ID: CHEMBL240 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19034038	Inhibitor 8504		1.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Dry cough 2 Sources: http://www.epharmapedia.com/medicine/profile/248625/Silomat-Compositum.html?lang=en&tab=druginfo	Palliative		Approved 8583	Silomat Approved Use Indications: for those diseases that are characterized by coughing rebel, especially if associated with respiratory failure. Cough in patients with obstructive bronchitis in adults and children. Pictures Paroxysmal spasmodic cough in children. Chronic bronchitis, emphysema and pneumoconiosis that is accompanied by coughing. Launch Date 1961

Doses

Dose	Population	Adverse events
240 mg 3 times / day multiple, oral Highest studied dose Dose: 240 mg, 3 times / day Route: oral Route: multiple Dose: 240 mg, 3 times / day Sources: https://www.ema.europa.eu/en/documents/referral/clobutinol-article-107-procedures-annex-ii_en.pdf	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.ema.europa.eu/en/documents/referral/clobutinol-article-107-procedures-annex-ii_en.pdf	Disc. AE: QT prolonged... AEs leading to discontinuation/dose reduction: QT prolonged Sources: https://www.ema.europa.eu/en/documents/referral/clobutinol-article-107-procedures-annex-ii_en.pdf
4 mg/mL 3 times / day multiple, oral Studied dose Dose: 4 mg/mL, 3 times / day Route: oral Route: multiple Dose: 4 mg/mL, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2095610/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/2095610/	Sources: https://pubmed.ncbi.nlm.nih.gov/2095610/

AEs

AE	Significance	Dose	Population
QT prolonged	Disc. AE	240 mg 3 times / day multiple, oral Highest studied dose Dose: 240 mg, 3 times / day Route: oral Route: multiple Dose: 240 mg, 3 times / day Sources: https://www.ema.europa.eu/en/documents/referral/clobutinol-article-107-procedures-annex-ii_en.pdf	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.ema.europa.eu/en/documents/referral/clobutinol-article-107-procedures-annex-ii_en.pdf

PubMed

Title	Date	PubMed
Keeping the rhythm: hERG and beyond in cardiovascular safety pharmacology.	2010-05	22111613
Clobutinol delays ventricular repolarization in the guinea pig heart: comparison with cardiac effects of HERG K+ channel inhibitor E-4031.	2009-12	19770670
Unclear loss of consciousness after clobutinol intake.	2009-08-10	19464130
N-of-1 double-blind, randomized controlled trial of tramadol to treat chronic cough.	2009-05	19539101
[Two cases of suspected Munchausen by proxy syndrome: the importance of forensic toxicological analyses in handling suspicions and producing evidence].	2009-02-17	19216366
Effects of common antitussive drugs on the hERG potassium channel current.	2008-12	19034038
Clobutinol: severe cardiac arrhythmias. Old drugs should also be monitored.	2008-06	18630356
New validated liquid chromatographic and chemometrics-assisted UV spectroscopic methods for the determination of two multicomponent cough mixtures in syrup.	2008-04-02	18376584
[Risks of non-prescription medication. Clobutinol cough syrup as a recent example].	2008-01	18197591
Allergy evaluation after emergency treatment: anaphylaxis to the over-the-counter medication clobutinol.	2007-03	17351213
Flow injection potentiometric determination of clobutinol hydrochloride.	2006-04-15	18970592
A common antitussive drug, clobutinol, precipitates the long QT syndrome 2.	2004-11	15280442
[Comparative study of two antitussive drugs in the treatment of acute dry cough of infectious origin (prospective, randomized, single blind study)].	2003-03-04	12611200
Bioterrorism and how to cope with it.	2002-09-05	12208621
Important drugs for cough in advanced cancer.	2001-11	11762966

Patents

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 Created by `admin` on `Mon Mar 31 18:30:26 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:26 GMT 2025`
Record UNII	1NY2IX043A
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

IVERSAL

Preferred Name

English

CLOBUTINOL

Official Name

English

BENZENEETHANOL, 4-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA.-METHYL-

Systematic Name

English

CLOBUTINOL [MI]

Common Name

English

Clobutinol [WHO-DD]

Common Name

English

KAT-256 FREE BASE

Code

English

R05DB03

Code

English

P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA.-METHYLPHENETHYL ALCOHOL

Common Name

English

clobutinol [INN]

Common Name

English

KAT 256 FREE BASE

Code

English

Classification Tree Code System Code

WHO-VATC

QR05DB03