U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C23H16O6.2C21H27NO
Molecular Weight 1007.2599
Optical Activity ( + / - )
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENPROPERINE PAMOATE

SMILES

CC(COC1=CC=CC=C1CC2=CC=CC=C2)N3CCCCC3.CC(COC4=CC=CC=C4CC5=CC=CC=C5)N6CCCCC6.OC(=O)C7=CC8=C(C=CC=C8)C(CC9=C%10C=CC=CC%10=CC(C(O)=O)=C9O)=C7O

InChI

InChIKey=VSVBMXAKSJDLCL-UHFFFAOYSA-N
InChI=1S/C23H16O6.2C21H27NO/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;2*1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19/h1-10,24-25H,11H2,(H,26,27)(H,28,29);2*2,4-7,10-13,18H,3,8-9,14-17H2,1H3

HIDE SMILES / InChI
Molecular Formula C23H16O6
Molecular Weight 388.3695
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C21H27NO
Molecular Weight 309.4452
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
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

Unknown
149124
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
Cofrel

Approved Use

Symptomatic relief of cough.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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

PubMed

TitleDatePubMed
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
[Nondestructive quantitative analysis of Cofrel medicines by improved partial least squares-NIR spectroscopy].
2007-06
Identification and quantitative determination of benproperine metabolites in human plasma and urine by liquid chromatography-tandem mass spectrometry.
2006-01-02
Identification of some benproperine metabolites in humans and investigation of their antitussive effect.
2005-12
Anti-tussive activity of benproperine enantiomers on citric-acid-induced cough in conscious guinea-pigs.
2004-02
Patents

Patents

JP2013544815A
3

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:29:24 GMT 2025
Edited
by admin
on Mon Mar 31 19:29:24 GMT 2025
Record UNII
370C8CB2K3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENPROPERINE EMBONATE
WHO-DD  
Preferred Name English
BENPROPERINE PAMOATE
MI  
Common Name English
PIPERIDINE, 1-(1-METHYL-2-(2-(PHENYLMETHYL)PHENOXY)ETHYL)-, 4,4'-METHYLENEBIS(3-HYDROXY-2-NAPHTHALENECARBOXYLATE) (2:1)
Systematic Name English
Benproperine embonate [WHO-DD]
Common Name English
TUSSAFUG
Brand Name English
BENPROPERINE PAMOATE [MI]
Common Name English
2-NAPHTHALENECARBOXYLIC ACID, 4,4'-METHYLENEBIS(3-HYDROXY-, COMPD. WITH 1-(1-METHYL-2-(2-(PHENYLMETHYL)PHENOXY)ETHYL)PIPERIDINE (1:2)
Systematic Name English
ASA-1585 PAMOATE
Code English
Code System Code Type Description
CAS
64238-92-2
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY
PUBCHEM
91663270
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY
RXCUI
236750
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY RxNorm
FDA UNII
370C8CB2K3
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY
ECHA (EC/EINECS)
264-745-5
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY
EVMPD
SUB00704MIG
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY
MERCK INDEX
m2321
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY Merck Index
SMS_ID
100000084997
Created by admin on Mon Mar 31 19:29:24 GMT 2025 , Edited by admin on Mon Mar 31 19:29:24 GMT 2025
PRIMARY
Related Record Type Details
Structure of BENPROPERINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BENPROPERINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966