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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29NO2.C10H8O3S.H2O
Molecular Weight 565.72
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOPROPOXYPHENE NAPSYLATE

SMILES

O.OS(=O)(=O)C1=CC2=C(C=CC=C2)C=C1.CCC(=O)O[C@](CC3=CC=CC=C3)([C@@H](C)CN(C)C)C4=CC=CC=C4

InChI

InChIKey=GBKONKCASNNUQD-ATVRCVQASA-N
InChI=1S/C22H29NO2.C10H8O3S.H2O/c1-5-21(24)25-22(18(2)17-23(3)4,20-14-10-7-11-15-20)16-19-12-8-6-9-13-19;11-14(12,13)10-6-5-8-3-1-2-4-9(8)7-10;/h6-15,18H,5,16-17H2,1-4H3;1-7H,(H,11,12,13);1H2/t18-,22+;;/m0../s1

HIDE SMILES / InChI
Molecular Formula C10H8O3S
Molecular Weight 208.234
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C22H29NO2
Molecular Weight 339.4712
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

LEVOPROPOXYPHENE is an antitussive drug, one of enantiomer of propoxyphene. Pdropoxyphene is an analgesic in the opioid category, patented in 1955 and manufactured by Eli Lilly and Company. Pdropoxyphene is intended to treat mild pain and also has antitussive (cough suppressant) and local anaesthetic effects.

Originator

Approval Year

1962
69
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
NOVRAD

Approved Use

Unknown

Launch Date

1962
Doses

Doses

DosePopulationAdverse events​
100 mg 6 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14010800/
unhealthy, adult
n = 50
Health Status: unhealthy
Condition: nonproductive cough
Age Group: adult
Sex: M+F
Population Size: 50
Sources:
https://pubmed.ncbi.nlm.nih.gov/14010800/
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea
Sources:
https://pubmed.ncbi.nlm.nih.gov/14010800/
AEs

AEs

AESignificanceDosePopulation
Nausea Disc. AE
100 mg 6 times / day multiple, oral
Highest studied dose
Dose: 100 mg, 6 times / day
Route: oral
Route: multiple
Dose: 100 mg, 6 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/14010800/
unhealthy, adult
n = 50
Health Status: unhealthy
Condition: nonproductive cough
Age Group: adult
Sex: M+F
Population Size: 50
Sources:
https://pubmed.ncbi.nlm.nih.gov/14010800/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1524

CYP2C19
1478
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
1692
 no [Activation >10 uM]
CYP2C19
1553
 no [Activation >10 uM]
CYP2C9
1819
 no [Activation >10 uM]
CYP3A4
1925
 yes [Activation 5.01187 uM]
CYP2D6
1891
 yes [Activation 7.94328 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:51174
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51174
ZINC
ZINC000001530767
http://zinc15.docking.org/substances/ZINC000001530767
PubMed

PubMed

TitleDatePubMed
Patents

Patents

US4012525
4

Sample Use Guides

In Vivo Use Guide
The disposition of propoxyphene and its major biotransformation product norpropoxyphene was studied in normal subjects following a single 130 mg oral dose.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:15:54 GMT 2023
Edited
by admin
on Fri Dec 15 17:15:54 GMT 2023
Record UNII
KK9590R73S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOPROPOXYPHENE NAPSYLATE
USAN   USP-RS  
USAN  
Official Name English
LY-29866
Code English
LEVOPROPOXYPHENE NAPSYLATE [USAN]
Common Name English
2-NAPHTHALENESULFONIC ACID COMPOUND WITH (-)-.ALPHA.-(2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA.-PHENYLPHENETHYL PROPIONATE (1:1) MONOHYDRATE
Systematic Name English
BENZENEETHANOL, .ALPHA.-(2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA.-PHENYL-, PROPANOATE (ESTER), (R-(R*,S*))-, COMPD. WITH 2-NAPHTHALENESULFONIC ACID (1:1), MONOHYDRATE
Systematic Name English
LILLY 29866
Code English
Levopropoxyphene napsilate [WHO-DD]
Common Name English
LILLY-29866
Code English
LEVOPROPOXYPHENE NAPSILATE
WHO-DD  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66917
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
Code System Code Type Description
CAS
5667-69-6
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
SUPERSEDED
SMS_ID
100000086126
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
CAS
55557-30-7
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
FDA UNII
KK9590R73S
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
RXCUI
402519
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C90774
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
CAS
7247-77-0
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
SUPERSEDED
PUBCHEM
16051927
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
EVMPD
SUB02912MIG
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID901014588
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
ChEMBL
CHEMBL1738990
Created by admin on Fri Dec 15 17:15:54 GMT 2023 , Edited by admin on Fri Dec 15 17:15:54 GMT 2023
PRIMARY
Related Record Type Details
Structure of LEVOPROPOXYPHENE NAPSYLATE ANHYDROUS
ANHYDROUS->SOLVATE
Structure of LEVOPROPOXYPHENE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of LEVOPROPOXYPHENE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
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