Dextropropoxyphene

"Paradex" redirects here. For the antiseptic trade named Peridex, see Chlorhexidine. For the oral anticoagulant trade named Pradaxa, see Dabigatran.

Dextropropoxyphene
Clinical data
Trade namesDarvon
AHFS/Drugs.comMonograph
MedlinePlusa682325
License data
Pregnancy
category
  • AU: C
Addiction
liability		Low[1][failed verification]
Routes of
administration		By mouth, IV, rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability40%[3]
Protein binding78%[3]
MetabolismLiver-mediated, CYP3A4-mediated N-demethylation (major), aromatic hydroxylation (minor) and ester hydrolysis (minor)[3]
Elimination half-life6–12 hours; 30–36 hours (active metabolite, nordextropropoxyphene)[4]
ExcretionUrine (major), breastmilk (minor)[3]
Identifiers
  • (1S,2R)-1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propionate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.747 Edit this at Wikidata
Chemical and physical data
FormulaC22H29NO2
Molar mass339.479 g·mol−1
3D model (JSmol)
Melting point75 °C (167 °F)
  • CCC(=O)O[C@](Cc1ccccc1)(c2ccccc2)[C@H](C)CN(C)C
  • 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+/m1/s1 checkY
  • Key:XLMALTXPSGQGBX-GCJKJVERSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Dextropropoxyphene[5] is an analgesic in the opioid category, patented in 1955[6] 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 anaesthetic effects. The drug has been taken off the market in Europe and the US due to concerns of fatal overdoses and heart arrhythmias.[7] It is still available in Australia, albeit with restrictions after an application by its manufacturer to review its proposed banning.[8] Its onset of analgesia (pain relief) is said to be 20–30 minutes and peak effects are seen about 1.5–2.0 hours after oral administration.[3]

Dextropropoxyphene is sometimes combined with acetaminophen. Trade names include Darvocet-N, Di-Gesic,[9] and Darvon with APAP (for dextropropoxyphene and paracetamol).[10] 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paracetamol/dextropropoxyphene preparation is co-proxamol (sold under a variety of brand names); however, it has been withdrawn since 2007, and is no longer available to new patients, with exceptions.[11] The paracetamol combination(s) are known as Capadex or Di-Gesic in Australia,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).

Dextropropoxyphene is known under several synonyms, including:

  • Alpha-d-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol propionate
  • [(2S,3R)-4-(Dimethylamino)-3- methyl-1,2-diphenylbutan-2-yl] propanoate
  • (+)-1,2-Diphenyl-2-propionoxy- 3-methyl-4-di-methylaminobutane
  • Desoxypropiophen
  1. ^ "Drug Scheduling". Drug Enforcement Administration. Retrieved 2024-01-22.
  2. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-03.
  3. ^ a b c d e Davis MP, Glare PA, Hardy J (2009) [2005]. Opioids in Cancer Pain (2nd ed.). Oxford, UK: Oxford University Press. ISBN 978-0-19-157532-7.
  4. ^ "PRODUCT INFORMATION PARADEX" (PDF). TGA eBusiness Services. Aspen Pharmacare Australia Pty Ltd. 2 March 2010. Retrieved 9 April 2014.
  5. ^ US 2728779, Pohland A, "Esters of Substituted Aminobutanes", issued 27 December 1955, assigned to Eli Lilly and Company. 
  6. ^ "Dextropropoxyphen". RÖMPP Online. Stuttgart: Georg Thieme Verlag KG. 30 April 2013.
  7. ^ Gandey A (2 February 2011). "Physicians Say Good Riddance to 'Worst Drug in History'". Medscape.
  8. ^ "Dextropropoxyphene questions and answers". Therapeutic Goods Administration (TGA). Commonwealth of Australia. 7 January 2014.
  9. ^ "Consumer Medicine Information: Digesic" (PDF). Aspen Pharmacare Australia Pty Ltd. Archived from the original (PDF) on 2009-09-14. Retrieved 2009-03-12.
  10. ^ Nursing 2000 Drug Handbook. Springhouse, Pennsylvania: Springhouse Corp. 2000. p. 306. ISBN 978-0-87434-993-1.
  11. ^ British National Formulary (BNF) (57th ed.). London, UK: Pharmaceutical Press. 2009. ISBN 978-0-85369-845-6.