Dextropropoxyphene

Structural formula
General
Non-proprietary name	Dextropropoxyphene
other names	(2 S , 3 R ) -4- (Dimethylamino) -3-methyl-1,2-diphenyl-2-butanylpropionate ( IUPAC )
Molecular formula	C 22 H 29 NO 2
Brief description	White, crystalline powder (dextropropoxyphene hydrochloride)
External identifiers / databases
EC number	207-420-5
ECHA InfoCard	100.006.747
PubChem	10100
ChemSpider	9696
DrugBank	DB00647
Wikidata	Q2268608
Drug information
ATC code	N02 AC04
Drug class	Opioid - analgesic ; Diphenylpropylamine derivative;
properties
Molar mass	339.48 g · mol -1
Melting point	75–76 ° C (free base, enantiomer); 163–168.5 ° C (hydrochloride, enantiomer);
solubility	soluble in water , acetone, ethanol and chloroform (hydrochloride)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	282 mg kg −1 ( LD 50 , mouse , oral ) ; 111 mg kg −1 ( LD 50 , mouse , ip ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dextropropoxyphene is a fully synthetic opioid with moderate pain relieving effectiveness. Dextropropoxyphene is a pure agonist on the μ-opioid receptor .

history

Dextropropoxyphene was patented by Lilly in 1955 as a strong analgesic and was sold by Gödecke ( Develin retard , capsules of 150 mg). The hydrochloride of dextropropoxyphene was used medicinally. In Germany, dextropropoxyphene is listed in Appendix II of the Narcotics Act and has no longer been available for prescription without exception.

pharmacology

effect

As an opioid, dextropropoxyphene has the same profile of effects and side effects, and thus essentially the same risk potential as other opioids.

Its single dose analgesic equivalence is one twentieth that of morphine . A dose of 150 to 300 mg (in adults) of the sustained-release preparation given at the beginning has an analgesic effect for 8 to 12 hours.

Side effects

Side effects can occur with dextropropoxyphene that exceeds the pre-existing tolerance to opioids due to pre-consumption. These are tiredness, sleep disorders , drowsiness , nausea , vomiting , edema in the legs, urinary retention and constipation . They usually go away as tolerance develops or the dose is reduced. Sleep and sexual disorders last the longest .

Use during pregnancy and lactation: Dextropropoxyphene has an effect on the fetus when taken during pregnancy.

Trade names

Monopreparations (all aV): Develin retard (D), Darvon, Darvon-N (CA), Deprancol (NL, B)

literature

ASP
Beilstein EIV 13, 2221
DAB 1996 and Komm.
Hager (5th) 7, 1242-1246 .- [HS 292219; CAS number: 469-62-5 (d.); 1639-60-7 (hydrochloride)]
Römpp Lexikon Chemie , Georg Thieme Verlag , Stuttgart - New York, 1997, p. 928.
Hermann PT Ammon et al .: Hunnius Pharmaceutical Dictionary . 9th edition, Walter de Gruyter Verlag , Berlin - New York, 2004, ISBN 3-11-017475-8 geb. and ISBN 3-11-017487-1 brosch., p. 436.
THE MERCK INDEX, 15th edition, The Royal Society of Chemistry 2013, ISBN 978-1-84973-670-1 , p. 1452.

Individual evidence

↑ European Pharmacopoeia Commission (Ed.): EUROPEAN PHARMACOPOE 5TH EDITION . tape 5.0-5.7 , 2006.
↑ ^a ^b ^c ^d ^e p Gangolli: The Dictionary of Substances and Their Effects: O-S . Royal Society of Chemistry, 1999, ISBN 978-0-85404-833-5 , pp. 573 ( limited preview in Google Book search).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. In: Stein Husebø , Eberhard Klaschik (ed.): Palliative medicine. 5th edition, Springer, Heidelberg 2009, ISBN 3-642-01548-4 , pp. 207-313, here: p. 234.

[Ph._Eur._5-1] European Pharmacopoeia Commission (Ed.): EUROPEAN PHARMACOPOE 5TH EDITION . tape 5.0-5.7 , 2006.

[S._Gangolli-2] ↑ ^a ^b ^c ^d ^e p Gangolli: The Dictionary of Substances and Their Effects: O-S . Royal Society of Chemistry, 1999, ISBN 978-0-85404-833-5 , pp. 573 ( limited preview in Google Book search).

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Eberhard Klaschik : Pain therapy and symptom control in palliative medicine. In: Stein Husebø , Eberhard Klaschik (ed.): Palliative medicine. 5th edition, Springer, Heidelberg 2009, ISBN 3-642-01548-4 , pp. 207-313, here: p. 234.