CLOBUTINOL HYDROCHLORIDE

Details

Stereochemistry	MIXED
Molecular Formula	C14H22ClNO.ClH
Molecular Weight	292.245
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ZMROYCGIWPNZNJ-UHFFFAOYSA-N

InChI=1S/C14H22ClNO.ClH/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;1H

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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Clobutinol is a cough suppressant that is withdrawn from the US and EU markets.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 92 Target ID: CHEMBL240 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19034038	Inhibitor 8297		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 8429	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

PubMed

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

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 `Fri Dec 15 16:58:44 GMT 2023` Edited by `admin` on `Fri Dec 15 16:58:44 GMT 2023`
Record UNII	N2U6799DZQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOBUTINOL HYDROCHLORIDE

Common Name

English

CLOBUTINOL HYDROCHLORIDE [MI]

Common Name

English

KAT-256

Code

English

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

Common Name

English

Clobutinol hydrochloride [WHO-DD]

Common Name

English

KAT 256

Code

English

SILOMAT

Common Name

English

CLOBUTINOL HCL

Common Name

English

CLOBUTINOL HYDROCHLORIDE [MART.]

Common Name

English

CLOBUTINOL HYDROCHLORIDE [JAN]

Common Name

English

Code System Code Type Description

FDA UNII

N2U6799DZQ