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

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29NO2.C10H8O3S
Molecular Weight 547.705
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOPROPOXYPHENE NAPSYLATE ANHYDROUS

SMILES

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=VZPXFHVJUUSVLH-VNJAQMQMSA-N
InChI=1S/C22H29NO2.C10H8O3S/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)/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 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
70
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
Health Status: unhealthy
Age Group: adult
Sex: M+F
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
Health Status: unhealthy
Age Group: adult
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/14010800/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2C19
2057
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 no [Activation >10 uM]
CYP2C19
2141
 no [Activation >10 uM]
CYP2C9
2497
 no [Activation >10 uM]
CYP3A4
2633
 yes [Activation 5.01187 uM]
CYP2D6
2546
 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
[POISONING BY INGESTION OF AN EXCESSIVE DOSE OF LEVOPROPOXYPHENE (LETUSIN)].
1964
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 Mon Mar 31 17:47:18 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:18 GMT 2025
Record UNII
W7DQT6KY5S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOPROPOXYPHENE NAPSYLATE ANHYDROUS
ORANGE BOOK  
Common Name English
LEVOPROPOXYPHENE 2-NAPHTHALENESULFONATE
MI  
Preferred Name English
2-NAPHTHALENESULFONIC ACID COMPOUND WITH (-)-.ALPHA.-(2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA.-PHENYLPHENETHYL PROPIONATE (1:1)
Systematic Name English
LEVOPROPOXYPHENE NAPSYLATE, ANHYDROUS
Common Name English
BENZENEETHANOL, .ALPHA.-(2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA.-PHENYL-, PROPANOATE (ESTER), (R-(R*,S*))-, COMPD. WITH 2-NAPHTHALENESULFONIC ACID (1:1)
Common Name English
LEVOPROPOXYPHENE 2-NAPHTHALENESULFONATE [MI]
Common Name English
LEVOPROPOXYPHENE NAPSYLATE ANHYDROUS [ORANGE BOOK]
Common Name English
LEVOPROPOXYPHENE NAPSILATE ANHYDROUS
Common Name English
NOVRAD
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C66917
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
Code System Code Type Description
FDA UNII
W7DQT6KY5S
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
227-209-1
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
PUBCHEM
6604497
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
SMS_ID
100000086126
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
DRUG BANK
DBSALT001392
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
MERCK INDEX
m6793
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL1738990
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
NCI_THESAURUS
C90775
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID8045563
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
CAS
5714-90-9
Created by admin on Mon Mar 31 17:47:18 GMT 2025 , Edited by admin on Mon Mar 31 17:47:18 GMT 2025
PRIMARY
Related Record Type Details
Structure of LEVOPROPOXYPHENE
PARENT -> SALT/SOLVATE
Structure of LEVOPROPOXYPHENE NAPSYLATE
SOLVATE->ANHYDROUS
Related Record Type Details
Structure of LEVOPROPOXYPHENE
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