dextropropoxyphene

Also known as (+)-alpha-propoxyphene, Darvon®, propoxyphene, d-Propoxyphene, alpha-D-4-Dimethylamino-3-methyl-1,2-diphenyl-2-butanol-propionat, alpha-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol propionate ester, Dextropropoxyphen, Destropropossifene

Dextropropoxyphene is an opioid analgesic patented in 1955 and manufactured by Eli Lilly and Company. It is an optical isomer of levopropoxyphene. It is intended to treat mild pain and also has antitussive (cough suppressant) and local anesthetic effects. The drug has been taken off the market in Europe and the United States due to concerns of fatal overdoses and heart arrhythmias. It is still available in Australia, albeit with restrictions after an application by its manufacturer to review its proposed banning. Its onset of analgesia (pain relief) is said to be 20–30 minutes and peak effects

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.class: Opioid
Drug.verifiedrevid: 460780758
Drug.IUPAC_name: (1S,2R)-1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propionate
Drug.image: Dextropropoxyphene structure.svg
Drug.image_class: skin-invert-image
Drug.width: 200px
Drug.image2: Dextropropoxyphene3DanJ.gif
Drug.image_class2: bg-transparent
Drug.width2: 200px
Drug.tradename: Darvon, Darvocet
Drug.MedlinePlus: a682325
Drug.licence_US: Propoxyphene
Drug.pregnancy_AU: C
Drug.legal_AU: S4
Drug.legal_BR: A2
Drug.legal_CA: Schedule I

via Wikipedia infobox

Chemical data

Formula: C22H29NO2
Molecular weight: 339.5 g/mol
IUPAC name: [(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate
SMILES: CCC(=O)O[C@](CC1=CC=CC=C1)(C2=CC=CC=C2)[C@H](C)CN(C)C
InChIKey: XLMALTXPSGQGBX-GCJKJVERSA-N
XLogP: 4.2
Polar surface area: 29.5 Å²
H-bond donors: 0
H-bond acceptors: 3
Formal charge: 0

via PubChem

Research

1,965 papers

via PubMed

Wikidata facts

Mass: 339.219829

Show 6 more facts

isomeric SMILES: CCC(=O)O[C@@](CC1=CC=CC=C1)([C@H](C)CN(C)C)C2=CC=CC=C2
chemical formula: C₂₂H₂₉NO₂
canonical SMILES: CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C
NCI Thesaurus ID: C61912
World Health Organisation international non-proprietary name: dextropropoxyphene
Commons category: Dextropropoxyphene

Sources (5)

via Wikidata · CC0

~17 min read

Article

25 sections

Contents

Medical uses
Analgesia
Restless legs syndrome
Available forms
Contraindications
Side effects
Pharmacology
Toxicity
History
Use in organic synthesis
Society and culture
Usage controversy and regulation
Australia
Canada
European Union
New Zealand
India
Sweden
United Kingdom
United States
In media
Use by right-to-die societies
Drug testing
See also
References

Dextropropoxyphene is sometimes combined with paracetamol (acetaminophen). Trade names include Darvocet-N, Di-Gesic, and Darvon with APAP (for dextropropoxyphene and paracetamol). The British approved name (i.e. the generic name of the active ingredient) of the paracetamol/dextropropoxyphene preparation is co-proxamol (sold under a variety of brand names); however, it has been withdrawn since 2007, and is no longer available to new patients, with exceptions. The paracetamol combinations are known as Capadex or Di-Gesic in Australia, Lentogesic in South Africa, and Di-Antalvic in France (unlike co-proxamol, which is an approved name, these are all brand names).