Identification

Name
Clofedanol
Accession Number
DB04837
Type
Small Molecule
Groups
Approved, Withdrawn
Description

Clofedanol is a centrally-acting cough suppressant available in Canada under the trade name Ulone. It is not available in the United States.

Structure
Thumb
Synonyms
  • Chlophedianol
  • clofedanol
  • Clofedanolum
  • Clofedianolo
Product Ingredients
IngredientUNIICASInChI Key
Chlophedianol hydrochloride69QQ58998Y511-13-7XYGSFNHCFFAJPO-UHFFFAOYSA-N
Clofedanol hydrochlorideNot AvailableNot AvailableNot applicable
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
UloneSyrup25 mgOralValeant Canada Lp Valeant Canada S.E.C.1962-12-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Abanatuss PedChlophedianol hydrochloride (25 mg/5mL) + Dexchlorpheniramine maleate (2 mg/5mL) + Pseudoephedrine hydrochloride (60 mg/5mL)SolutionOralKramer Novis.2015-07-01Not applicableUs
Abanatuss Ped DropsChlophedianol hydrochloride (6.25 mg/1mL) + Dexchlorpheniramine maleate (0.5 mg/1mL) + Pseudoephedrine hydrochloride (15 mg/1mL)SolutionOralKramer Novis.2015-08-05Not applicableUs
Atuss DaChlophedianol hydrochloride (12.5 mg/5mL) + Brompheniramine maleate (2 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralAber Pharmaceuticals, Llc2016-02-08Not applicableUs
Atuss DaChlophedianol hydrochloride (12.5 mg/5mL) + Brompheniramine maleate (2 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralCarwin Associates, Inc2016-10-25Not applicableUs
BicloraChlophedianol hydrochloride (12.5 mg/5mL) + Chlorcyclizine hydrochloride (12.5 mg/5mL)LiquidOralPhysicians Total Care, Inc.2013-01-02Not applicableUs
BicloraChlophedianol hydrochloride (25 mg/1) + Chlorcyclizine hydrochloride (25 mg/1)TabletOralHawthorn Pharmaceuticals, Inc.2012-11-302014-10-23Us
BicloraChlophedianol hydrochloride (12.5 mg/5mL) + Chlorcyclizine hydrochloride (12.5 mg/5mL)LiquidOralHawthorn Pharmaceuticals, Inc.2012-10-312014-10-23Us
biclora-DChlophedianol hydrochloride (12.5 mg/5mL) + Chlorcyclizine hydrochloride (12.5 mg/5mL) + Pseudoephedrine hydrochloride (30 mg/5mL)LiquidOralHawthorn Pharmaceuticals, Inc.2012-10-082014-10-23Us
biclora-DChlophedianol hydrochloride (25 mg/1) + Chlorcyclizine hydrochloride (25 mg/1) + Pseudoephedrine hydrochloride (60 mg/1)TabletOralHawthorn Pharmaceuticals, Inc.2012-11-302014-11-30Us
Carbaphen CHChlophedianol hydrochloride (24 mg/5mL) + Chlorpheniramine maleate (4 mg/5mL) + Phenylephrine hydrochloride (10 mg/5mL)SuspensionOralGil Pharmaceutical Corp2011-12-29Not applicableUs
International/Other Brands
Antitussin
Categories
UNII
42C50P12AP
CAS number
791-35-5
Weight
Average: 289.8
Monoisotopic: 289.123341974
Chemical Formula
C17H20ClNO
InChI Key
WRCHFMBCVFFYEQ-UHFFFAOYSA-N
InChI
InChI=1S/C17H20ClNO/c1-19(2)13-12-17(20,14-8-4-3-5-9-14)15-10-6-7-11-16(15)18/h3-11,20H,12-13H2,1-2H3
IUPAC Name
1-(2-chlorophenyl)-3-(dimethylamino)-1-phenylpropan-1-ol
SMILES
CN(C)CCC(O)(C1=CC=CC=C1)C1=CC=CC=C1Cl

Pharmacology

Indication

Used in the treatment of dry cough.

Associated Conditions
Pharmacodynamics

Chlophedianol (or Clofedanol) is a centrally-acting cough suppressant. It has local anesthetic and antihistamine properties, and may have anticholinergic effects at high doses.

Mechanism of action

Suppresses the cough reflex by a direct effect on the cough center in the medulla of the brain.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Clofedanol.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Clofedanol.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Clofedanol.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Clofedanol.
AmphetamineAmphetamine may decrease the sedative and stimulatory activities of Clofedanol.
BenzphetamineBenzphetamine may decrease the sedative and stimulatory activities of Clofedanol.
Benzylpenicilloyl PolylysineClofedanol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Clofedanol.
ChlorphentermineChlorphentermine may decrease the sedative and stimulatory activities of Clofedanol.
DextroamphetamineDextroamphetamine may decrease the sedative and stimulatory activities of Clofedanol.
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

References

Synthesis Reference

Lorenz, R., Gosswald, R. and Henecka, H.; US. Patent 3,031,377; April 24, 1962; assigned to Farbenfabriken Bayer AG, Germany.

General References
Not Available
External Links
Human Metabolome Database
HMDB0015585
PubChem Compound
2795
PubChem Substance
46505324
ChemSpider
2693
ChEBI
135207
ChEMBL
CHEMBL1201313
Therapeutic Targets Database
DAP001080
PharmGKB
PA164748134
Drugs.com
Drugs.com Drug Page
Wikipedia
Clofedanol
ATC Codes
R05DB10 — Clofedanol
AHFS Codes
  • 48:08.00 — Antitussives

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
SolutionOral
SuspensionOral
Tablet, multilayerOral
TabletOral
LiquidOral
SyrupOral
Solution / dropsOral
SyrupOral25 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)120 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0621 mg/mLALOGPS
logP3.51ALOGPS
logP3.46ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)13.18ChemAxon
pKa (Strongest Basic)8.87ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.94 m3·mol-1ChemAxon
Polarizability31.25 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9892
Blood Brain Barrier+0.9474
Caco-2 permeable+0.7603
P-glycoprotein substrateSubstrate0.6468
P-glycoprotein inhibitor INon-inhibitor0.6719
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterInhibitor0.5846
CYP450 2C9 substrateNon-substrate0.7596
CYP450 2D6 substrateSubstrate0.619
CYP450 3A4 substrateSubstrate0.754
CYP450 1A2 substrateNon-inhibitor0.5972
CYP450 2C9 inhibitorNon-inhibitor0.8098
CYP450 2D6 inhibitorInhibitor0.8482
CYP450 2C19 inhibitorNon-inhibitor0.7196
CYP450 3A4 inhibitorNon-inhibitor0.6746
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6213
Ames testNon AMES toxic0.8129
CarcinogenicityNon-carcinogens0.7042
BiodegradationNot ready biodegradable0.9928
Rat acute toxicity2.7383 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.755
hERG inhibition (predictor II)Inhibitor0.7948
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0pb9-9560000000-539851d74afb04d60422
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Chlorobenzenes / Aralkylamines / Aryl chlorides / Tertiary alcohols / 1,3-aminoalcohols / Trialkylamines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Diphenylmethane / Chlorobenzene / Aralkylamine / Halobenzene / Aryl chloride / Aryl halide / 1,3-aminoalcohol / Tertiary alcohol / Tertiary aliphatic amine / Tertiary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Histamine receptor activity
Specific Function
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
Gene Name
HRH1
Uniprot ID
P35367
Uniprot Name
Histamine H1 receptor
Molecular Weight
55783.61 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  4. Maurer H, Pfleger K: Identification and differentiation of alkylamine antihistamines and their metabolites in urine by computerized gas chromatography-mass spectrometry. J Chromatogr. 1988 Aug 19;430(1):31-41. [PubMed:2905706]

Drug created on September 26, 2007 08:12 / Updated on November 18, 2018 13:32