BENPROPERINE PHOSPHATE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H27NO.H3O4P
Molecular Weight	407.4404
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OP(O)(O)=O.CC(COC1=C(CC2=CC=CC=C2)C=CC=C1)N3CCCCC3

InChI

InChIKey=MCVUURBOSHQXMK-UHFFFAOYSA-N

InChI=1S/C21H27NO.H3O4P/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19;1-5(2,3)4/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3;(H3,1,2,3,4)

HIDE SMILES / InChI

Description
Sources: http://www.mims.com/hongkong/drug/info/cofrel
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/16297353 and http://www.ncbi.nlm.nih.gov/pubmed/5301345

Benproperine (Cofrel) is a cough suppressant. It is used for symptomatic relief of cough. Cofrel is 2-4 times as potent as codeine in suppressing cough in animals. It acts peripherally by blocking afferent sensory nerve impulses originating from receptors in the lungs and pleura.

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cough 106 Sources: http://www.mims.com/hongkong/drug/info/cofrel/?type=brief#Indications	Palliative		Approved 8583	Cofrel Approved Use Symptomatic relief of cough.

C_max

Value	Dose	Analyte	Population
333 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12567913/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
153 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12567913/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE, (R)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
146.4 ng/mL EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-YWYY200902004.htm	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
4257 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12567913/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2010 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12567913/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE, (R)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
5234.31 ng × h/mL EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-YWYY200902004.htm	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
17 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12567913/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12567913/	60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE, (R)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
24.7 h EXPERIMENT https://en.cnki.com.cn/Article_en/CJFDTotal-YWYY200902004.htm	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	BENPROPERINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
80 mg single, oral Highest studied dose Dose: 80 mg Route: oral Route: single Dose: 80 mg Sources: http://wprim.whocc.org.cn/admin/article/articleDetail?WPRIMID=518300&articleId=518300	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: http://wprim.whocc.org.cn/admin/article/articleDetail?WPRIMID=518300&articleId=518300	Sources: http://wprim.whocc.org.cn/admin/article/articleDetail?WPRIMID=518300&articleId=518300

PubMed

Title	Date	PubMed
Resonance light scattering study on the interaction of benproperine phosphate with eriochrome blue black R in the presence of sodium dodecylbenzene sulphonate and its analytical application.	2008-09-19	18800357
[Nondestructive quantitative analysis of Cofrel medicines by improved partial least squares-NIR spectroscopy].	2007-06	17763766
Identification and quantitative determination of benproperine metabolites in human plasma and urine by liquid chromatography-tandem mass spectrometry.	2006-01-02	16280263
Identification of some benproperine metabolites in humans and investigation of their antitussive effect.	2005-12	16297353
Anti-tussive activity of benproperine enantiomers on citric-acid-induced cough in conscious guinea-pigs.	2004-02	15005888

Patents

Sample Use Guides

In Vivo Use Guide

1 or 2 tablets 3 times daily, according to severity of cough. Tablets should be swallowed whole and not chewed.

Route of Administration: Oral

In Vitro Use Guide

10(-5) g/ml of Benproperine (ASA 158/5) caused remarkable reduction of the contraction of the tracheal muscle preparation of a guinea pig caused by histamine HCl.

Name

Type

Language

BENPROPERINE TRIHYDROGEN PHOSPHATE

Preferred Name

English

BENPROPERINE PHOSPHATE

Common Name

English

ASA-158/5

Code

English

ASA 158/5

Code

English

BENPROPERINE PHOSPHATE [JAN]

Common Name

English

Benproperine phosphate [WHO-DD]

Common Name

English

BENPROPERINE TRIHYDROGEN PHOSPHATE [MI]

Common Name

English

PIREXYL

Common Name

English

1-(2-(2-BENZYLPHENOXY)-1-METHYLETHYL)PIPERIDINE MONOPHOSPHATE

Systematic Name

English

Code System Code Type Description

MERCK INDEX

m2321