CHLOPHEDIANOL

US Approved OTC

First approved in 1960

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H20ClNO
Molecular Weight	289.8
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CCC(O)(C1=CC=CC=C1)C2=C(Cl)C=CC=C2

InChI

InChIKey=WRCHFMBCVFFYEQ-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB04837
Curator's Comment: description was created based on several sources, including http://www.hmdb.ca/metabolites/HMDB15585 | https://www.ncbi.nlm.nih.gov/pubmed/24671376

Chlophedianol (Clofedanol) is a centrally-acting cough suppressant, although the mechanism of action is not known. It is available in Canada under the trade name Ulone. It is not available in the United States. Chlophedianol (Clofedanol) suppresses the cough reflex by a direct effect on the cough center in the medulla of the brain. It also has local anesthetic and antihistamine properties, and may have anticholinergic effects at high doses.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: https://www.drugs.com/mmx/ulone.html	Primary		Approved 8429	ULONE Approved Use Indicated for the symptomatic relief of nonproductive cough. Chlophedianol is used to provide relief of acute cough due to minor throat and bronchial irritation occurring with colds or inhaled irritants.

Doses

Dose	Population	Adverse events
20 mg 3 times / day steady, oral Recommended Dose: 20 mg, 3 times / day Route: oral Route: steady Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6749701/	healthy, adult n = 12 Health Status: healthy Condition: cough Age Group: adult Sex: unknown Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/6749701/	Disc. AE: Allergic rash... AEs leading to discontinuation/dose reduction: Allergic rash (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/6749701/

AEs

AE	Significance	Dose	Population
Allergic rash	1 patient Disc. AE	20 mg 3 times / day steady, oral Recommended Dose: 20 mg, 3 times / day Route: oral Route: steady Dose: 20 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6749701/	healthy, adult n = 12 Health Status: healthy Condition: cough Age Group: adult Sex: unknown Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/6749701/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT 192 CYP 270

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/604421/	yes
UGT 192	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/604421/	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY572090	https://www.001chemical.com/chem/791-35-5
3B Scientific (Wuhan) Corp	3B2-1344	http://www.3bsc.com/index/pro_info.php?id=55060
Aurora Fine Chemicals LLC	A17.949.718	http://online.aurorafinechemicals.com/info?ID=A17.949.718
ChemMol	30105052	http://www.chemmol.com/chemmol/30105052.html
ChemMol	99143451	http://www.chemmol.com/chemmol/99143451.html
Finetech	FT-0747781	http://www.finetechnology-ind.com/prod/detail/pub/791-35-5.html
LGC Standards	LGCFOR3030.00	https://www.lgcstandards.com/US/en/p/LGCFOR3030.00
Molcore	MC572090	https://www.molcore.com/product/791-35-5
Sigma-Aldrich	PH010350_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/ph010350
Smolecule	S524005	http://www.smolecule.com/products/s524005
THE BioTek	bt-263863	https://www.thebiotek.com/product/inhibitors/bt-263863
Yuhao Chemical	RT2848	http://www.chemyuhao.com/511-13-7.html
iChemical	EBD3071517	http://www.ichemical.com/products/791-35-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Chlophedianol Hydrochloride: A New Antitussive Agent.	1960 Dec 17	20326564
Clinical evaluation of chlophedianol a new nonnarcotic antitussive.	1962 Sep	14478530
A comparative randomized double-blind clinical trial of isoaminile citrate and chlophedianol hydrochloride as antitussive agents.	1982 Aug	6749701
[Controlled double-blind study on the efficacy of clofedanol-sobrerol in the treatment of pediatric pertussis].	1984 Dec 31	6398399
Therapeutic options for acute cough due to upper respiratory infections in children.	2012 Feb	21892785

Patents

Sample Use Guides

In Vivo Use Guide

Usual adult and adolescent dose is 25 mg every six to eight hours as needed.

Route of Administration: Oral

In Vitro Use Guide

The inhibition of specific binding of [3H]dextromethorphan (4 nM) to guinea pig brain homogenate was determined. Chlophedianol, a phenylalkylamine, had an IC value of 1300 nM.

Name

Type

Language

CHLOPHEDIANOL

Common Name

English

1-PHENYL-1-(O-CHLOROPHENYL)-3-DIMETHYLAMINOPROPANOL

Common Name

English

BENZENEMETHANOL, 2-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)- .ALPHA.-PHENYL

Common Name

English

CHLOPHEDIANOL [MI]

Common Name

English

Clofedanol [WHO-DD]

Common Name

English

NSC-113595

Code

English

1-O-CHLOROPHENYL-1-PHENYL-3-DIMETHYLAMINO-1-PROPANOL

Systematic Name

English

CLOFEDANOL

Official Name

English

clofedanol [INN]

Common Name

English

CHLOPHEDIANOL [VANDF]

Common Name

English

ANTITUSSIN

Brand Name

English

TUSSISTOP

Brand Name

English

Classification Tree Code System Code

WHO-ATC

R05DB10