LEVOPROPOXYPHENE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H29NO2
Molecular Weight	339.4712
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)O[C@](CC1=CC=CC=C1)([C@@H](C)CN(C)C)C2=CC=CC=C2

InChI

InChIKey=XLMALTXPSGQGBX-PGRDOPGGSA-N

InChI=1S/C22H29NO2/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/h6-15,18H,5,16-17H2,1-4H3/t18-,22+/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB06793

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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&varApplNo=012928	Primary		Approved 8429	NOVRAD Approved Use Unknown Launch Date -2.45635203E11

Doses

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2C19 1478

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTM5MDYifX0%3D	no [Activation >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTM5MDYifX0%3D	no [Activation >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTM5MDYifX0%3D	no [Activation >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU5MzkwNiJ9fQ%3D%3D	yes [Activation 5.01187 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU5MzkwNiJ9fQ%3D%3D	yes [Activation 7.94328 uM]

Sourcing

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

PubMed

Title	Date	PubMed
[POISONING BY INGESTION OF AN EXCESSIVE DOSE OF LEVOPROPOXYPHENE (LETUSIN)].	1964	14254473

Patents

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

Name

Type

Language

LEVOPROPOXYPHENE

Official Name

English

LEVOPROPOXYPHENE [MI]

Common Name

English

PROPOXYPHENE, L-

Common Name

English

LEVOPROPOXYPHENE [HSDB]

Common Name

English

(.ALPHA.R)-.ALPHA.-((1S)-2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA.-PHENYLBENZENEETHANOL PROPANOATE (ESTER)

Common Name

English

L-PROPOXYPHENE

Common Name

English

Levopropoxyphene [WHO-DD]

Common Name

English

(-)-PROPOXYPHENE

Common Name

English

PROPOXYPHENE, (-)-

Common Name

English

levopropoxyphene [INN]

Common Name

English

(-)-.ALPHA.-(2-(DIMETHYLAMINO)-1-METHYLETHYL)-.ALPHA-PHENYLPHENETHYL PROPIONATE

Common Name

English

Code System Code Type Description

PUBCHEM

200742