Dextropropoxyphene

Dextropropoxyphene
Clinical data
Trade names	Darvon
AHFS/Drugs.com	Monograph
MedlinePlus	a682325
License data	US FDA: Propoxyphene;
Pregnancy; category	AU: C;
Addiction; liability	Low
Routes of; administration	By mouth, IV, rectal
ATC code	N02AC04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class A2 (Narcotic drugs); CA: Schedule I; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class C; US: Schedule II and Schedule IV (when in dosage form);
Pharmacokinetic data
Bioavailability	40%
Protein binding	78%
Metabolism	Liver-mediated, CYP3A4-mediated N-demethylation (major), aromatic hydroxylation (minor) and ester hydrolysis (minor)
Elimination half-life	6–12 hours; 30–36 hours (active metabolite, nordextropropoxyphene)
Excretion	Urine (major), breastmilk (minor)
Identifiers
	IUPAC name (1S,2R)-1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl propionate;
CAS Number	469-62-5 ;
PubChem CID	10100;
IUPHAR/BPS	7593;
DrugBank	DB00647 ;
ChemSpider	9696 ;
UNII	S2F83W92TK;
KEGG	D07809 ;
ChEBI	CHEBI:51173 ;
ChEMBL	ChEMBL1213351 ;
CompTox Dashboard (EPA)	DTXSID1023524 ;
ECHA InfoCard	100.006.747
Chemical and physical data
Formula	C22H29NO2
Molar mass	339.479 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	75 °C (167 °F)
	SMILES CCC(=O)O[C@](Cc1ccccc1)(c2ccccc2)[C@H](C)CN(C)C;
	InChI 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 ; Key:XLMALTXPSGQGBX-GCJKJVERSA-N ;
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Dextropropoxyphene is an analgesic in the opioid category, 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 anaesthetic effects. The drug has been taken off the market in Europe and the US 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 are seen about 1.5–2.0 hours after oral administration.

Dextropropoxyphene is sometimes combined with 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 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

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