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
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.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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:
unhealthy, adult
n = 50
Health Status: unhealthy
Condition: nonproductive cough
Age Group: adult
Sex: M+F
Population Size: 50
Sources:
Disc. AE: Nausea...
AEs leading to
discontinuation/dose reduction:
Nausea
Sources:
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:
unhealthy, adult
n = 50
Health Status: unhealthy
Condition: nonproductive cough
Age Group: adult
Sex: M+F
Population Size: 50
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [Activation >10 uM]
no [Activation >10 uM]
no [Activation >10 uM]
yes [Activation 5.01187 uM]
yes [Activation 7.94328 uM]
PubMed

PubMed

TitleDatePubMed
[POISONING BY INGESTION OF AN EXCESSIVE DOSE OF LEVOPROPOXYPHENE (LETUSIN)].
1964
Patents

Patents

Sample Use Guides

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
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