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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:53 UTC
HMDB IDHMDB0015585
Secondary Accession Numbers
  • HMDB15585
Metabolite Identification
Common NameChlophedianol
DescriptionClofedanol, also known as chlophedianol or antitussin, belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups. A diarylmethane that is 2-chlorophenyl(phenyl)methane substituted on the methane carbon by a 2-(dimethylamino)ethyl group. Clofedanol is a drug which is used in the treatment of dry cough. Clofedanol is a very strong basic compound (based on its pKa). Clofedanol is a potentially toxic compound. Used in the treatment of dry cough, it suppresses the cough reflex by a direct effect on the cough centre in the medulla of the brain.
Structure
Data?1582753313
Synonyms
ValueSource
ChlophedianolChEBI
ClofedanolumChEBI
AntitussinKegg
Chlophendianol hydrochlorideMeSH
2-Chloro-alpha-(2-dimethylaminoethyl)benzhydrolMeSH
BaltixMeSH
Clofedanol hydrochlorideMeSH
1-(2-Chlorophenyl)-3-(dimethylamino)-1-phenyl-1-propanolHMDB
1-Phenyl-1-(O-chlorophenyl)-3-dimethylaminopropanolHMDB
2-chloro-alpha-(2-(dimethylamino)Ethyl)benzhydrolHMDB
alpha-(Dimethylaminoethyl)-O-chlorobenzhydrolHMDB
ChlofedanolHMDB
ClofedanoHMDB
ClofedanolHMDB
Clophedianol baseHMDB
1-(10-(3-(4-(2-Hydroxyethyl)-1-piperazinyl)propyl)phenothiazin-2-yl)-1-propanoneChEBI
CarfenazinaChEBI
CarfenazineChEBI
CarfenazinumChEBI
CarphenazinHMDB
2-(ACETYLOXY)benzoIC ACIDChEBI
2-Acetoxybenzenecarboxylic acidChEBI
2-Acetoxybenzoic acidChEBI
AcetylsalicylateChEBI
AcetylsalicylsaeureChEBI
Acide 2-(acetyloxy)benzoiqueChEBI
Acide acetylsalicyliqueChEBI
Acido acetilsalicilicoChEBI
Acidum acetylsalicylicumChEBI
ASAChEBI
AzetylsalizylsaeureChEBI
EasprinChEBI
O-Acetoxybenzoic acidChEBI
O-Acetylsalicylic acidChEBI
O-Carboxyphenyl acetateChEBI
Salicylic acid acetateChEBI
Acetylsalicylic acidKEGG
AspalonKEGG
DurlazaKEGG
2-(ACETYLOXY)benzoateGenerator
2-AcetoxybenzenecarboxylateGenerator
2-AcetoxybenzoateGenerator
O-AcetoxybenzoateGenerator
O-AcetylsalicylateGenerator
O-Carboxyphenyl acetic acidGenerator
Salicylate acetateGenerator
Salicylic acid acetic acidGenerator
2-Carboxyphenyl acetateHMDB
AcenterineHMDB
AcetardHMDB
AceticylHMDB
AcetolHMDB
AcetonylHMDB
AcetophenHMDB
AcetosalHMDB
AcetosalinHMDB
AcetylinHMDB
AcetyonylHMDB
AcetysalHMDB
Acetysalicylic acidHMDB
AcylpyrinHMDB
AsatardHMDB
AspergumHMDB
AspirdropsHMDB
BenaspirHMDB
BialpiriniaHMDB
BufferinHMDB
CaprinHMDB
CardioaspirinaHMDB
EcolenHMDB
EcotrinHMDB
EmpirinHMDB
EndosprinHMDB
EndydolHMDB
O-(Acetyloxy)benzoateHMDB
O-(Acetyloxy)benzoic acidHMDB
PersistinHMDB
PharmacinHMDB
PolopirynaHMDB
PremaspinHMDB
RheumintablettenHMDB
RhodineHMDB
SalcetogenHMDB
SaletinHMDB
SalospirHMDB
SolprinHMDB
Solprin acidHMDB
SolpyronHMDB
TasprinHMDB
TemperalHMDB
ToldexHMDB
TriaminicinHMDB
MagnecylHMDB
PolopirinHMDB
SolupsanHMDB
ZorprinHMDB
DisprilHMDB
AloxiprimumHMDB
ColfaritHMDB
MicristinHMDB
Acid, acetylsalicylicHMDB
2-(ACETYLOXY)benzoIC ACIDChEBI
2-Acetoxybenzenecarboxylic acidChEBI
2-Acetoxybenzoic acidChEBI
AcetylsalicylateChEBI
AcetylsalicylsaeureChEBI
Acide 2-(acetyloxy)benzoiqueChEBI
Acide acetylsalicyliqueChEBI
Acido acetilsalicilicoChEBI
Acidum acetylsalicylicumChEBI
ASAChEBI
AzetylsalizylsaeureChEBI
EasprinChEBI
O-Acetoxybenzoic acidChEBI
O-Acetylsalicylic acidChEBI
O-Carboxyphenyl acetateChEBI
Salicylic acid acetateChEBI
Acetylsalicylic acidKEGG
AspalonKEGG
DurlazaKEGG
2-(ACETYLOXY)benzoateGenerator
2-AcetoxybenzenecarboxylateGenerator
2-AcetoxybenzoateGenerator
O-AcetoxybenzoateGenerator
O-AcetylsalicylateGenerator
O-Carboxyphenyl acetic acidGenerator
Salicylate acetateGenerator
Salicylic acid acetic acidGenerator
2-Carboxyphenyl acetateHMDB
AcenterineHMDB
AcetardHMDB
AceticylHMDB
AcetolHMDB
AcetonylHMDB
AcetophenHMDB
AcetosalHMDB
AcetosalinHMDB
AcetylinHMDB
AcetyonylHMDB
AcetysalHMDB
Acetysalicylic acidHMDB
AcylpyrinHMDB
AsatardHMDB
AspergumHMDB
AspirdropsHMDB
BenaspirHMDB
BialpiriniaHMDB
BufferinHMDB
CaprinHMDB
CardioaspirinaHMDB
EcolenHMDB
EcotrinHMDB
EmpirinHMDB
EndosprinHMDB
EndydolHMDB
O-(Acetyloxy)benzoateHMDB
O-(Acetyloxy)benzoic acidHMDB
PersistinHMDB
PharmacinHMDB
PolopirynaHMDB
PremaspinHMDB
RheumintablettenHMDB
RhodineHMDB
SalcetogenHMDB
SaletinHMDB
SalospirHMDB
SolprinHMDB
Solprin acidHMDB
SolpyronHMDB
TasprinHMDB
TemperalHMDB
ToldexHMDB
TriaminicinHMDB
MagnecylHMDB
PolopirinHMDB
SolupsanHMDB
ZorprinHMDB
DisprilHMDB
AloxiprimumHMDB
ColfaritHMDB
MicristinHMDB
Acid, acetylsalicylicHMDB
2-(ACETYLOXY)benzoIC ACIDChEBI
2-Acetoxybenzenecarboxylic acidChEBI
2-Acetoxybenzoic acidChEBI
AcetylsalicylateChEBI
AcetylsalicylsaeureChEBI
Acide 2-(acetyloxy)benzoiqueChEBI
Acide acetylsalicyliqueChEBI
Acido acetilsalicilicoChEBI
Acidum acetylsalicylicumChEBI
ASAChEBI
AzetylsalizylsaeureChEBI
EasprinChEBI
O-Acetoxybenzoic acidChEBI
O-Acetylsalicylic acidChEBI
O-Carboxyphenyl acetateChEBI
Salicylic acid acetateChEBI
Acetylsalicylic acidKEGG
AspalonKEGG
DurlazaKEGG
2-(ACETYLOXY)benzoateGenerator
2-AcetoxybenzenecarboxylateGenerator
2-AcetoxybenzoateGenerator
O-AcetoxybenzoateGenerator
O-AcetylsalicylateGenerator
O-Carboxyphenyl acetic acidGenerator
Salicylate acetateGenerator
Salicylic acid acetic acidGenerator
2-Carboxyphenyl acetateHMDB
AcenterineHMDB
AcetardHMDB
AceticylHMDB
AcetolHMDB
AcetonylHMDB
AcetophenHMDB
AcetosalHMDB
AcetosalinHMDB
AcetylinHMDB
AcetyonylHMDB
AcetysalHMDB
Acetysalicylic acidHMDB
AcylpyrinHMDB
AsatardHMDB
AspergumHMDB
AspirdropsHMDB
BenaspirHMDB
BialpiriniaHMDB
BufferinHMDB
CaprinHMDB
CardioaspirinaHMDB
EcolenHMDB
EcotrinHMDB
EmpirinHMDB
EndosprinHMDB
EndydolHMDB
O-(Acetyloxy)benzoateHMDB
O-(Acetyloxy)benzoic acidHMDB
PersistinHMDB
PharmacinHMDB
PolopirynaHMDB
PremaspinHMDB
RheumintablettenHMDB
RhodineHMDB
SalcetogenHMDB
SaletinHMDB
SalospirHMDB
SolprinHMDB
Solprin acidHMDB
SolpyronHMDB
TasprinHMDB
TemperalHMDB
ToldexHMDB
TriaminicinHMDB
MagnecylHMDB
PolopirinHMDB
SolupsanHMDB
ZorprinHMDB
DisprilHMDB
AloxiprimumHMDB
ColfaritHMDB
MicristinHMDB
Acid, acetylsalicylicHMDB
2-(ACETYLOXY)benzoIC ACIDChEBI
2-Acetoxybenzenecarboxylic acidChEBI
2-Acetoxybenzoic acidChEBI
AcetylsalicylateChEBI
AcetylsalicylsaeureChEBI
Acide 2-(acetyloxy)benzoiqueChEBI
Acide acetylsalicyliqueChEBI
Acido acetilsalicilicoChEBI
Acidum acetylsalicylicumChEBI
ASAChEBI
AzetylsalizylsaeureChEBI
EasprinChEBI
O-Acetoxybenzoic acidChEBI
O-Acetylsalicylic acidChEBI
O-Carboxyphenyl acetateChEBI
Salicylic acid acetateChEBI
Acetylsalicylic acidKEGG
AspalonKEGG
DurlazaKEGG
2-(ACETYLOXY)benzoateGenerator
2-AcetoxybenzenecarboxylateGenerator
2-AcetoxybenzoateGenerator
O-AcetoxybenzoateGenerator
O-AcetylsalicylateGenerator
O-Carboxyphenyl acetic acidGenerator
Salicylate acetateGenerator
Salicylic acid acetic acidGenerator
2-Carboxyphenyl acetateHMDB
AcenterineHMDB
AcetardHMDB
AceticylHMDB
AcetolHMDB
AcetonylHMDB
AcetophenHMDB
AcetosalHMDB
AcetosalinHMDB
AcetylinHMDB
AcetyonylHMDB
AcetysalHMDB
Acetysalicylic acidHMDB
AcylpyrinHMDB
AsatardHMDB
AspergumHMDB
AspirdropsHMDB
BenaspirHMDB
BialpiriniaHMDB
BufferinHMDB
CaprinHMDB
CardioaspirinaHMDB
EcolenHMDB
EcotrinHMDB
EmpirinHMDB
EndosprinHMDB
EndydolHMDB
O-(Acetyloxy)benzoateHMDB
O-(Acetyloxy)benzoic acidHMDB
PersistinHMDB
PharmacinHMDB
PolopirynaHMDB
PremaspinHMDB
RheumintablettenHMDB
RhodineHMDB
SalcetogenHMDB
SaletinHMDB
SalospirHMDB
SolprinHMDB
Solprin acidHMDB
SolpyronHMDB
TasprinHMDB
TemperalHMDB
ToldexHMDB
TriaminicinHMDB
MagnecylHMDB
PolopirinHMDB
SolupsanHMDB
ZorprinHMDB
DisprilHMDB
AloxiprimumHMDB
ColfaritHMDB
MicristinHMDB
Acid, acetylsalicylicHMDB
Chemical FormulaC17H20ClNO
Average Molecular Weight289.8
Monoisotopic Molecular Weight289.123341974
IUPAC Name1-(2-chlorophenyl)-3-(dimethylamino)-1-phenylpropan-1-ol
Traditional Namebaltix
CAS Registry Number791-35-5
SMILES
CN(C)CCC(O)(C1=CC=CC=C1)C1=CC=CC=C1Cl
InChI Identifier
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
InChI KeyWRCHFMBCVFFYEQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes 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
  • Chlorobenzene
  • Aralkylamine
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • 1,3-aminoalcohol
  • Tertiary alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organooxygen compound
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.062 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.062 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity84.94 m³·mol⁻¹ChemAxon
Polarizability31.25 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6920000000-9663bc4c9b4c6cddf803Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000l-3190000000-c824c404a084a83de8cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0490000000-3b2ca74cacc7304a7ac4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0007-0290000000-6bbcb1c25f0ce2866aa3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-3900000000-14ead6824a79b1c917d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-f2501d0b07fcc1bbf258Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002r-6190000000-130788ec7458ac9f9483Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00or-9450000000-03b65fc4b4d7b5b0a9dfSpectrum
MSMass Spectrum (Electron Ionization)splash10-0pb9-9560000000-539851d74afb04d60422Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04837 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04837 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04837
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClofedanol
METLIN IDNot Available
PubChem Compound2795
PDB IDNot Available
ChEBI ID135207
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
55783.6
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 ]