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Identification
NameClofedanol
Accession NumberDB04837
TypeSmall Molecule
GroupsApproved, Withdrawn
DescriptionClofedanol 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
Antitussin
Chlophedianol
Clofedanolum
Clofedianolo
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ulonesyrup25 mgoralValeant Canada Lp Valeant Canada S.E.C.1962-12-31Not applicableCanada
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Abanatuss PedKramer Novis
Abanatuss Ped DropsKramer Novis
Atuss DaAber Pharmaceuticals, Llc
BicloraPhysicians Total Care, Inc.
Carbaphen ChGil Pharmaceutical Corp
Carbaphen Ped ChGil Pharmaceutical Corp
Chlo HistR. A. Mc Neil Company
Chlo TussR.A. Mc Neil Company
Chlo Tuss EXR. A. Mc Neil Company
CloferaCentrix Pharmaceutical, Inc.
ClophedPortal Pharmaceutical
Dicel CDCentrix Pharmaceutical
DonatussinLaser Pharmaceuticals, LLC
Drymax AFJay Mac Pharmaceuticals
NinjacofCenturion Labs, Llc
Ninjacof-ACenturion Labs, Llc
Panatuss PedSeyer Pharmatec, Inc.
Poly Hist PdPoly Pharmaceuticals, Inc.
Pro-chloPro Pharma, Llc
TexaclearGm Pharmaceuticals
Texaclear Fast Acting Allergy ReliefGm Pharmaceuticals, Inc.
VanacofGm Pharmaceuticals
Vanacof-8Gm Pharmaceuticals,Inc
Salts
Name/CASStructureProperties
Chlophedianol hydrochloride
ThumbNot applicableDBSALT001414
Clofedanol hydrochloride
ThumbNot applicableDBSALT001029
Categories
UNII42C50P12AP
CAS number791-35-5
WeightAverage: 289.8
Monoisotopic: 289.123341974
Chemical FormulaC17H20ClNO
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylmethanes
Direct ParentDiphenylmethanes
Alternative Parents
Substituents
  • Diphenylmethane
  • Phenylpropylamine
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Tertiary alcohol
  • 1,3-aminoalcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in the treatment of dry cough.
PharmacodynamicsChlophedianol (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 actionSuppresses the cough reflex by a direct effect on the cough center in the medulla of the brain.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tabletoral
Suspensionoral
Syruporal
Solutionoral
Liquidoral
Solution/ dropsoral
Syruporal25 mg
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point120 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0pb9-9560000000-539851d74afb04d60422View in MoNA
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 ReferencesNot Available
External Links
ATC CodesR05DB10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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 catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
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 ]
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Drug created on September 26, 2007 08:12 / Updated on August 17, 2016 12:24