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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 of CLOBUTINOL HYDROCHLORIDE

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
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Clobutinol is a cough suppressant that is withdrawn from the US and EU markets.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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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

PubMed

TitleDatePubMed
Bioterrorism and how to cope with it.
2002 Jul-Aug
[Comparative study of two antitussive drugs in the treatment of acute dry cough of infectious origin (prospective, randomized, single blind study)].
2002 Sep-Oct
A common antitussive drug, clobutinol, precipitates the long QT syndrome 2.
2004 Nov
Keeping the rhythm: hERG and beyond in cardiovascular safety pharmacology.
2010 May
Patents

Sample Use Guides

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
JAN   MART.   MI   WHO-DD  
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
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID7047807
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
214-931-7
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
SMS_ID
100000088510
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
DRUG BANK
DBSALT002452
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
MERCK INDEX
m3630
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY Merck Index
EVMPD
SUB01348MIG
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
PUBCHEM
92876
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
CAS
1215-83-4
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL1474889
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY
RXCUI
235956
Created by admin on Fri Dec 15 16:58:44 GMT 2023 , Edited by admin on Fri Dec 15 16:58:44 GMT 2023
PRIMARY RxNorm
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY