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
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
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 |
DescriptionSources: http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/referrals/Clobutinol/human_referral_000117.jspCurator'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
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Clobutinol is a cough suppressant that is withdrawn from the US and EU markets.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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL240 Sources: http://www.ncbi.nlm.nih.gov/pubmed/19034038 |
1.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | Silomat Approved UseIndications: 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
Title | Date | PubMed |
---|---|---|
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/19770670
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
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Record UNII |
1NY2IX043A
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Record Status |
Validated (UNII)
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QR05DB03
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NCI_THESAURUS |
C66917
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WHO-ATC |
R05DB03
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238-926-4
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CLOBUTINOL
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CHEMBL1474889
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14860-49-2
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DB09004
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26937
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C78105
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DTXSID2022838
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1NY2IX043A
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100000084283
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686
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C017135
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SUB06680MIG
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21247
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m3630
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |