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

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Clobutinol is a cough suppressant that is withdrawn from the US and EU markets.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

-2.737152E11
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
Flow injection potentiometric determination of clobutinol hydrochloride.
2006 Apr 15
Clobutinol: severe cardiac arrhythmias. Old drugs should also be monitored.
2008 Jun
[Two cases of suspected Munchausen by proxy syndrome: the importance of forensic toxicological analyses in handling suspicions and producing evidence].
2008 Nov-Dec
Unclear loss of consciousness after clobutinol intake.
2009 Aug 10
Clobutinol delays ventricular repolarization in the guinea pig heart: comparison with cardiac effects of HERG K+ channel inhibitor E-4031.
2009 Dec
N-of-1 double-blind, randomized controlled trial of tramadol to treat chronic cough.
2009 May
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 16:31:28 UTC 2023
Edited
by admin
on Fri Dec 15 16:31:28 UTC 2023
Record UNII
1NY2IX043A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOBUTINOL
INN   MI   WHO-DD  
INN  
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
IVERSAL
Brand Name 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
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
NCI_THESAURUS C66917
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
WHO-ATC R05DB03
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
238-926-4
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
WIKIPEDIA
CLOBUTINOL
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL1474889
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
CAS
14860-49-2
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
DRUG BANK
DB09004
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
PUBCHEM
26937
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
NCI_THESAURUS
C78105
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID2022838
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
FDA UNII
1NY2IX043A
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
SMS_ID
100000084283
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
INN
2462
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
DRUG CENTRAL
686
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
MESH
C017135
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
EVMPD
SUB06680MIG
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY
RXCUI
21247
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY RxNorm
MERCK INDEX
m3630
Created by admin on Fri Dec 15 16:31:28 UTC 2023 , Edited by admin on Fri Dec 15 16:31:28 UTC 2023
PRIMARY Merck Index
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