CHLOPHEDIANOL HYDROCHLORIDE

US Approved OTC

First approved in 1960

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H20ClNO.ClH
Molecular Weight	326.261
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of CHLOPHEDIANOL HYDROCHLORIDE

Structure Search

SMILES

Cl.CN(C)CCC(O)(C1=CC=CC=C1)C2=CC=CC=C2Cl

InChI

InChIKey=XYGSFNHCFFAJPO-UHFFFAOYSA-N

InChI=1S/C17H20ClNO.ClH/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;1H

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 8583	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 Health Status: healthy Age Group: adult Sex: unknown 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 Health Status: healthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/6749701/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT 219 CYP 303

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP 303	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/604421/	yes
UGT 219	substrate 4014 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
iChemical	EBD3071517	http://www.ichemical.com/products/791-35-5.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
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

PubMed

Title	Date	PubMed
Therapeutic options for acute cough due to upper respiratory infections in children.	2012-02	21892785
[Controlled double-blind study on the efficacy of clofedanol-sobrerol in the treatment of pediatric pertussis].	1984-12-31	6398399
A comparative randomized double-blind clinical trial of isoaminile citrate and chlophedianol hydrochloride as antitussive agents.	1982-08	6749701
Clinical evaluation of chlophedianol a new nonnarcotic antitussive.	1962-09	14478530
Chlophedianol Hydrochloride: A New Antitussive Agent.	1960-12-17	20326564

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 HYDROCHLORIDE

Official Name

English

CLOFEDANOL HYDROCHLORIDE

Preferred Name

English

CLOFEDANOL HYDROCHLORIDE [MART.]

Common Name

English

COLDRIN

Brand Name

English

CLOFEDANOL HYDROCHLORIDE [JAN]

Common Name

English

ULONE

Brand Name

English

CHLOPHEDIANOL HCL

Common Name

English

CHLOPHEDIANOL HYDROCHLORIDE [MI]

Common Name

English

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

Systematic Name

English

Clofedanol hydrochloride [WHO-DD]

Common Name

English

SK-74

Common Name

English

SL-501

Code

English

PECTOLITAN

Brand Name

English

2-Chloro-?-[2-(dimethylamino)ethyl]benzhydrol hydrochloride

Systematic Name

English

SL 501

Code

English

CHLOPHEDIANOL HYDROCHLORIDE [USAN]

Common Name

English

ULO

Brand Name

English

CHLOPHEDIANOL HYDROCHLORIDE [ORANGE BOOK]

Common Name

English

BAYER-186

Code

English

Classification Tree Code System Code

CFR

21 CFR 341.14