DrugBank: Chlophedianol (DB04837)

targets (1)

Identification

Name

Chlophedianol

Accession Number

DB04837

Type

small molecule

Groups

approved

Description

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

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

1-(2-Chlorophenyl)-3-(dimethylamino)-1-phenyl-1-propanol
1-Phenyl-1-(o-chlorophenyl)-3-dimethylaminopropanol
2-Chloro-alpha-(2-(dimethylamino)ethyl)benzhydrol
Alpha-(dimethylaminoethyl)-o-chlorobenzhydrol
Chlofedanol
Clofedano
Clofedanol
Clofedanolum [inn-latin]
Clofedianolo [italian]
Clophedianol base

Brand names

Calmotusin
Coldrin
Dencyl
Detigon
Eutus
Tussistop
Ulo
Ulone

Brand name mixtures

Not Available

Categories

Anesthetics, Local
Antihistamines
Antitussive Agents

CAS number

791-35-5

Weight

Average: 289.8
Monoisotopic: 289.123341974

Chemical Formula

C₁₇H₂₀ClNO

InChI Key

InChIKey=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

Plain Text

IUPAC Name

1-(2-chlorophenyl)-3-(dimethylamino)-1-phenylpropan-1-ol

SMILES

CN(C)CCC(O)(C1=CC=CC=C1)C1=C(Cl)C=CC=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Diphenylmethanes

Substructures

Hydroxy Compounds
Benzyl Alcohols and Derivatives
Benzene and Derivatives
Aryl Halides
Halobenzenes
Aliphatic and Aryl Amines
Alcohols and Polyols
Diphenylmethanes
Aromatic compounds
Phenylpropylamines

Pharmacology

Indication

Used in the treatment of dry cough.

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.

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

Pharmacoeconomics

Manufacturers

3m pharmaceuticals inc

Packagers

Not Available

Dosage forms

Form	Route	Strength
Syrup	Oral

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	6.21e-02 g/l	ALOGPS
logP	3.51	ALOGPS
logP	3.46	ChemAxon Molconvert
logS	-3.67	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	2	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	23.47	ChemAxon Molconvert
rotatable bond count	5	ChemAxon Molconvert
refractivity	84.94	ChemAxon Molconvert
polarizability	31.25	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	2795
PubChem Substance	46505324
ChemSpider	2693
Therapeutic Targets Database	DAP001080
PharmGKB	PA10256
Drug Product Database	1966294
Drugs.com	http://www.drugs.com/cons/chlophedianol.html
Wikipedia	http://en.wikipedia.org/wiki/Clofedanol

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Avoid alcohol.
Take without regard to meals.

Targets
1. Histamine H1 receptor Pharmacological action: yes Actions: antagonist 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 Organism class: human UniProt ID: P35367 Gene: HRH1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed 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

Targets

1. Histamine H1 receptor

Pharmacological action: yes
Actions: antagonist

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

Organism class: human
UniProt ID: P35367 Link_out

Gene: HRH1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
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

Comments

Drug created on September 26, 2007 08:12 / Updated on November 18, 2010 17:59

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.