Clobutinol

Identification

Generic Name
Clobutinol
DrugBank Accession Number
DB09004
Background

Clobutinol is a cough suppressant that is withdrawn from the US and EU markets. Clobutinol may prolong the QT interval. In 2007, Clobutinol was determined to cause cardiac arrhythmia in some patients.

Type
Small Molecule
Groups
Withdrawn
Structure
Thumb
Weight
Average: 255.784
Monoisotopic: 255.138992038
Chemical Formula
C14H22ClNO
Synonyms
  • Clobutinol
External IDs
  • KAT 256

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Clobutinol hydrochlorideN2U6799DZQ1215-83-4ZMROYCGIWPNZNJ-UHFFFAOYSA-N

Categories

ATC Codes
R05DB03 — Clobutinol
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylbutylamines
Direct Parent
Phenylbutylamines
Alternative Parents
Phenylpropanes / Chlorobenzenes / Aralkylamines / Aryl chlorides / Tertiary alcohols / 1,3-aminoalcohols / Trialkylamines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,3-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Halobenzene / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
1NY2IX043A
CAS number
14860-49-2
InChI Key
KVHHQGIIZCJATJ-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-(4-chlorophenyl)-4-(dimethylamino)-2,3-dimethylbutan-2-ol
SMILES
CC(CN(C)C)C(C)(O)CC1=CC=C(Cl)C=C1

References

Synthesis Reference

U.S. Patent 3,121,087.

General References
  1. Bellocq C, Wilders R, Schott JJ, Louerat-Oriou B, Boisseau P, Le Marec H, Escande D, Baro I: A common antitussive drug, clobutinol, precipitates the long QT syndrome 2. Mol Pharmacol. 2004 Nov;66(5):1093-102. Epub 2004 Jul 27. [Article]
Human Metabolome Database
HMDB0032216
KEGG Drug
D07716
PubChem Compound
26937
PubChem Substance
310264964
ChemSpider
25085
RxNav
21247
ChEBI
94381
ChEMBL
CHEMBL1474889
Drugs.com
Drugs.com Drug Page
Wikipedia
Clobutinol

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionSubcutaneous
Solution / dropsOral
Syrup
Tablet, film coated
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
boiling point (°C)145-148U.S. Patent 3,121,087.
Predicted Properties
PropertyValueSource
Water Solubility0.535 mg/mLALOGPS
logP3.15ALOGPS
logP3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)14.64ChemAxon
pKa (Strongest Basic)9.41ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity74.04 m3·mol-1ChemAxon
Polarizability28.85 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on June 17, 2014 19:52 / Updated on February 21, 2021 18:52