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    Chemistry

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    Also known as: Dextropropoxyphene, D-propoxyphene, Dextropropoxyphen, Algafan, Dextroproxifeno, Destropropossifene
    Molecular Formula
    C22H29NO2
    Molecular Weight
    339.5  g/mol
    InChI Key
    XLMALTXPSGQGBX-GCJKJVERSA-N
    FDA UNII
    S2F83W92TK
    Dextropropoxyphene
    A narcotic analgesic structurally related to METHADONE. Only the dextro-isomer has an analgesic effect; the levo-isomer appears to exert an antitussive effect.
    Propoxyphene is an Opioid Agonist. The mechanism of action of propoxyphene is as a Full Opioid Agonist.
    1 2D Structure

    Dextropropoxyphene

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2S,3R)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate
    2.1.2 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
    2.1.3 InChI Key
    XLMALTXPSGQGBX-GCJKJVERSA-N
    2.1.4 Canonical SMILES
    CCC(=O)OC(CC1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C
    2.1.5 Isomeric SMILES
    CCC(=O)O[C@](CC1=CC=CC=C1)(C2=CC=CC=C2)[C@H](C)CN(C)C
    2.2 Other Identifiers
    2.2.1 UNII
    S2F83W92TK
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. D Propoxyphene

    2. D-propoxyphene

    3. Darvon

    4. Dextropropoxyphene

    5. Hydrochloride, Propoxyphene

    6. Propoxyphene Hydrochloride, (r*,r*)-(+-)-isomer

    7. Propoxyphene Hydrochloride, (r-(r*,r*))-isomer

    8. Propoxyphene Hydrochloride, (r-(r*,s*))-isomer

    9. Propoxyphene Hydrochloride, (s-(r*,r*))-isomer

    10. Propoxyphene Maleate, (+)-isomer

    11. Propoxyphene Phosphate, (s-(r*,s*))-isomer

    12. Propoxyphene Sulfate, (s-(r*,s*))-isomer

    2.3.2 Depositor-Supplied Synonyms

    1. Dextropropoxyphene

    2. D-propoxyphene

    3. Dextropropoxyphen

    4. Algafan

    5. Dextroproxifeno

    6. Destropropossifene

    7. Antalvic

    8. 469-62-5

    9. Depromic

    10. Proxagesic

    11. Femadol

    12. Dextropropoxifeno

    13. Propoxyphene, (+)-

    14. Dextropropoxyphenum

    15. Sk 65

    16. Propoxyphene, D-

    17. 4-dimethylamino-3-methyl-1,2-diphenyl-2-propoxybutane

    18. (+)-1,2-diphenyl-2-propionoxy-3-methyl-4-dimethylaminobutane

    19. (+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-propionyloxybutane

    20. Alpha-(+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol Propionate Ester

    21. (s)-alpha-(2-(dimethylamino)-1-methylethyl)-alpha-phenylbenzeneethanol Propanoate

    22. Alpha-d-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol-propionat

    23. Ii2g62ov6f

    24. S2f83w92tk

    25. Chebi:51173

    26. Sk-65

    27. (1s,2r)-1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl Propanoate

    28. 2-butanol, 4-(dimethylamino)-3-methyl-1,2-diphenyl-, Propionate (ester), (2s,3r)-

    29. J5.928e

    30. Dextropropoxyphene (inn)

    31. [(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] Propanoate

    32. 2-butanol, 4-(dimethylamino)-3-methyl-1,2-diphenyl-, Propionate, (+)-

    33. Dextroproxifeno [spanish]

    34. Propoxypene

    35. Destropropossifene [dcit]

    36. Dextropropoxyphene [inn]

    37. Alpha-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol Propionate

    38. Proxyvon

    39. Dextropropoxifeno [inn-spanish]

    40. Dextropropoxyphenum [inn-latin]

    41. (d)-propoxyphene

    42. Dextropropoxyphene [inn:ban]

    43. Hsdb 3175

    44. Einecs 207-420-5

    45. Unii-ii2g62ov6f

    46. Unii-s2f83w92tk

    47. Usaf El-84

    48. Bulk Dextropropoxyphene (non-dosage Forms)

    49. Propoxyphene-d

    50. Dea No. 9273

    51. Alpha-d-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol Propionate

    52. Propoxyphene, Dl-

    53. Alpha-d-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol-propionat [german]

    54. Darvon (salt/mix)

    55. Dolene (salt/mix)

    56. Abalgin (salt/mix)

    57. Doloxen (salt/mix)

    58. Erantin (salt/mix)

    59. Romidon (salt/mix)

    60. Benzeneethanol, Alpha-(2-(dimethylamino)-1-methylethyl)-alpha-phenyl-, Propanoate (ester), (s-(r*,s*))-

    61. Doloxene (salt/mix)

    62. C07406

    63. D07809

    64. .alpha.-d-propoxyphene

    65. (+)-alpha-propoxyphene

    66. Propoxyphene [mi]

    67. (+)-propoxyphene

    68. Alpha-(+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-propionoxybutane

    69. Propoxyphene [hsdb]

    70. Propoxyphene [vandf]

    71. Schembl25405

    72. Methanol, Compd. With (+-)-alpha-(2-dimethylamino)-1-methylethyl-alpha- Phenylphenethyl Propionate (1:1)

    73. (+/-)-propoxyphene

    74. Gtpl7593

    75. Chembl1213351

    76. Dtxsid1023524

    77. Bdbm82269

    78. Propoxyphene, (+/-)-

    79. Ids-nd-004(sect.2)

    80. Dextropropoxyphene [mart.]

    81. Dextropropoxyphene [who-dd]

    82. Benzeneethanol, .alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, Propanoate (ester), [s-(r*,s*)]-

    83. Zinc1530769

    84. Db00647

    85. 2621-61-6

    86. Benzeneethanol, Alpha-((1r)-2-(dimethylamino)-1-methylethyl)-alpha-phenyl-, Propanoate (ester), (alphas)-

    87. Cas_469-62-5

    88. Dextropropoxyphene 0.1 Mg/ml In Acetonitrile

    89. Dextropropoxyphene 1.0 Mg/ml In Acetonitrile

    90. Q2268608

    91. (+)-4-(dimethylamino)-3-methyl-1,2-diphenyl-2-butanol Propionate

    92. [(2s,3r)-4-dimethylamino-3-methyl-1,2-di(phenyl)butan-2-yl] Propanoate

    93. (2s,3r)-(+)-4-(dimethylamino)-3-methyl-1,2-diphenyl-2-butanol Propionate (ester)

    94. (2s,3r)-(+)-4-(dimethylamino)-3-methyl-1,2-diphenyl-2-butanol Propionate(ester)

    95. .alpha.-(+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol Propionate Ester

    96. 1-benzyl-3-(dimethylamino)-2-methyl-1-phenylpropyl Propionate, [s-(r*,s*)]- #

    97. (+)-propoxyphene Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

    98. Benzeneethanol, .alpha.-((1r)-2-(dimethylamino)-1-methylethyl)-.alpha.-phenyl-, 1-propanoate, (.alpha.s)-

    99. Benzeneethanol, .alpha.-((1r)-2-(dimethylamino)-1-methylethyl)-.alpha.-phenyl-, 1-propanoate, (.alpha.s)-rel-

    100. Benzeneethanol, .alpha.-[2-(dimethylamino)-1-methylethyl]-.alpha.-phenyl-, Propanoate, [s-(r*,s*)]-

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 339.5 g/mol
    Molecular Formula C22H29NO2
    XLogP34.2
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count9
    Exact Mass339.219829168 g/mol
    Monoisotopic Mass339.219829168 g/mol
    Topological Polar Surface Area29.5 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity397
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Analgesics, Opioid; Antitussive Agents; Narcotics

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    The U.S. Food and Drug Administration (FDA) is recommending against continued prescribing and use of the pain reliever propoxyphene because new data show that the drug can cause serious toxicity to the heart, even when used at therapeutic doses. FDA has requested that companies voluntarily withdraw propoxyphene from the United States market. Propoxyphene is an opioid pain reliever used to treat mild to moderate pain. It is sold under various names as a single-ingredient product (e.g., Darvon) and as part of a combination product with acetaminophen (e.g., Darvocet). FDA's recommendation is based on all available data including data from a new study that evaluated the effects that increasing doses of propoxyphene have on the heart. The results of the new study showed that when propoxyphene was taken at therapeutic doses, there were significant changes to the electrical activity of the heart: prolonged PR interval, widened QRS complex and prolonged QT interval. These changes, which can be seen on an electrocardiogram (ECG), can increase the risk for serious abnormal heart rhythms. FDA has concluded that the safety risks of propoxyphene outweigh its benefits for pain relief at recommended doses. ... Additional Information for Healthcare Professionals: FDA recommends that healthcare professionals: Stop prescribing and dispensing propoxyphene-containing products to patients. Contact patients currently taking propoxyphene-containing products and ask them to discontinue the drug. Inform patients of the risks associated with propoxyphene. Discuss alternative pain management strategies other than propoxyphene with your patients. Be aware of the possible risk of cardiac conduction abnormalities (prolonged QT, PR, and QRS intervals) in patients taking propoxyphene and assess patients for these events if they present with any signs or symptoms of arrhythmia. Report any side effects with propoxyphene to FDA's MedWatch program.

    US FDA; Drug Safety and Availability; FDA Drug Safety Communication: FDA Recommends Against the Continued Use of Propoxyphene (November 19, 2010). Available from, as of November 30, 2010: https://www.fda.gov/Drugs/DrugSafety/ucm234338.htm

    The U.S. Food and Drug Administration is asking manufacturers of prescription combination products that contain acetaminophen to limit the amount of acetaminophen to no more than 325 milligrams (mg) in each tablet or capsule. The FDA also is requiring manufacturers to update labels of all prescription combination acetaminophen products to warn of the potential risk for severe liver injury. /Combination products containing acetaminophen/

    US FDA; News and Events; Press Announcement: FDA Limits Acetaminophen in Prescription Combination Products; Requires Liver Toxicity Warnings; (January 13, 2011). Available from, as of March 27, 2011: https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm239894.htm

    Xanodyne Pharmaceuticals Inc. which makes Darvon and Darvocet, the brand version of the prescription pain medication propoxyphene, has agreed to withdraw the medication from the U.S. market at the request of the U.S. Food and Drug Administration. The FDA has also informed the generic manufacturers of propoxyphene-containing products of Xanodyne's decision and requested that they voluntarily remove their products as well. The FDA sought market withdrawal of propoxyphene after receiving new clinical data showing that the drug puts patients at risk of potentially serious or even fatal heart rhythm abnormalities. As a result of these data, combined with other information, including new epidemiological data, the agency concluded that the risks of the medication outweigh the benefits.

    US FDA; Drug Safety and Availability; FDA Drug Safety Communication: Xanodyne Agrees to Withdraw Propoxyphene From the U.S. Market (November 19, 2010). Available from, as of March 30, 2011:: https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/2010/ucm234350.htm

    For more Therapeutic Uses (Complete) data for (d)-PROPOXYPHENE (6 total), please visit the HSDB record page.

    4.2 Drug Warning

    One should be alert for evidence of inadequate propoxyphene analgesia in smokers (especially heavy smokers); selection of an alternative analgesic may be appropriate in such patients.

    Hansten P.D. Drug Interactions. 5th ed. Philadelphia: Lea and Febiger, 1985., p. 420

    Propoxyphene should be admin with caution to patients who are dependent on opiates. Because propoxyphene will not support morphine dependence, the sudden substitution of the usual dosage of propoxyphene for opiates may result in acute opiate withdrawal symptoms; these symptoms may be avoided by gradually reducing the dosage of the prior medication as propoxyphene is substituted.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2196

    Tolerance, psychologic dependence, and physical dependence have been reported in patients receiving propoxyphene. The dependence liability is qualitatively similar to that of codeine, but quantitatively less.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2196

    Propoxyphene has been willfully abused by dissolving propoxyphene pellets formerly contained in the Darvon Compound preparations in water and injecting the solution IV. Inadvertent injection into the brachial artery has resulted in digital gangrene necessitating amputation. Abuse by oral ingestion of large doses of propoxyphene hydrochloride has also been reported.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2196

    For more Drug Warnings (Complete) data for (d)-PROPOXYPHENE (13 total), please visit the HSDB record page.

    4.3 Minimum/Potential Fatal Human Dose

    Toxic doses for adults are stated to be 800 mg of the hydrochloride salt and 1200 mg of the napsylate salt. /Propoxyphene hydrochloride and napsylate/

    Gossel, T.A., J.D. Bricker. Principles of Clinical Toxicology. 3rd ed. New York, NY: Raven Press, Ltd., 1994., p. 301

    Toxic propoxyphene blood concentration: 30-60 ug/dL; Lethal propoxyphene blood concentration: 80-200 ug/dL /From table/

    Gossel, T.A., J.D. Bricker. Principles of Clinical Toxicology. 3rd ed. New York, NY: Raven Press, Ltd., 1994., p. 298

    4.4 Drug Indication

    For the relief of mild to moderate pain.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Propoxyphene, a synthetic opiate agonist, is structurally similar to methadone. Its general pharmacologic properties are those of the opiates as a group. The analgesic effect of propoxyphene is due to the d-isomer, dextropropoxyphene. It binds to the opiate receptors and leads to a decrease of the perception of pain stimuli. Propoxyphene possesses little to no antitussive activity and no antipyretic action.

    5.2 MeSH Pharmacological Classification

    Analgesics, Opioid

    Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)

    Narcotics

    Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PROPOXYPHENE
    5.3.2 FDA UNII
    S2F83W92TK
    5.3.3 Pharmacological Classes
    Established Pharmacologic Class [EPC] - Opioid Agonist
    5.4 ATC Code

    N - Nervous system

    N02 - Analgesics

    N02A - Opioids

    N02AC - Diphenylpropylamine derivatives

    N02AC04 - Dextropropoxyphene

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    The major route of metabolism is cytochrome CYP3A4 mediated N-demethylation to norpropoxyphene, which is excreted by the kidneys. In 48 hours, approximately 20% to 25% of the administered dose of propoxyphene is excreted via the urine, most of which is free or conjugated norpropoxyphene.

    Volume of Distribution

    16 L/kg

    Clearance

    2.6 L/min

    Following oral administration, propoxyphene hydrochloride and napsylate are absorbed principally in the upper small intestine. The napsylate salt appears to be absorbed more gradually than the hydrochloride salt. Equimolar doses of propoxyphene hydrochloride or napsylate provide similar plasma concentrations. The bioavailability of oral propoxyphene hydrochloride doses of 65, 130, or 195 mg is equivalent to that of oral propoxyphene napsylate doses of 100, 200, or 300 mg, respectively.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2197

    Peak plasma propoxyphene concentrations are usually achieved within 2-2.5 hours following oral administration of propoxyphene hydrochloride capsules or propoxyphene napsylate suspension (no longer commercially available in the US) and within 3 hours following oral administration of propoxyphene napsylate tablets. The analgesic effect occurs within 15 minutes to 1 hour and persists for 4-6 hours. Therapeutic plasma propoxyphene concentrations are 50 ng/mL or greater. Peak plasma concentrations achieved with the recommended 65-mg dose of propoxyphene hydrochloride may range from 50-120 ng/mL, while concentrations of the norpropoxyphene metabolite range from 100-200 ng/mL.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2197

    Only a small fraction of the absorbed dose (30%-70%) enters the general circulation in unmetabolized form. The rest is metabolized by intestinal and hepatic enzymes during absorption. Single dose kinetics indicate complete oral absorption. Peak plasma levels of propoxyphene after an oral 65 mg dose are 84-94 ng/ml (0.084-0.094 ug/ml) and are reached in 1.1-1.5 hr.

    Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 726

    The delay in absorption has been attributed to slower gastric emptying and/or the physical barrier produced by the food mass. The effect of meal composition on the absorption of propoxyphene /Darvon/ has been studied in 6 healthy volunteers. On an empty stomach, peak plasma levels occurred at about 2 hr, while ... high carbohydrate & high fat meals delayed peak times to about 3 hr & high protein to about 4 hr. Although the absorption rate was decreased by food, high carbohydrate & high protein meals slightly increased the overall bioavailability of propoxyphene.

    Hansten P.D. Drug Interactions. 5th ed. Philadelphia: Lea and Febiger, 1985., p. 419

    For more Absorption, Distribution and Excretion (Complete) data for (d)-PROPOXYPHENE (11 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Hepatic

    Propoxyphene undergoes extensive first-pass metabolism by intestinal and hepatic enzymes. Propoxyphene is metabolized mainly via N-demethylation (mediated by cytochrome P-450 (CYP) isoenzyme 3A4) to form norpropoxyphene. Ring hydroxylation and glucuronide formation appear to be minor metabolic pathways for the drug. Norpropoxyphene has an elimination half-life of 30-36 hours. Norpropoxyphene and unchanged propoxyphene are excreted mainly in urine. Approximately 20-25% of an orally administered 65-mg dose of propoxyphene hydrochloride may be recovered in urine as unchanged drug (trace amount) and free or conjugated norpropoxyphene within 48 hours.It appears that the unchanged drug is excreted mainly within 6 hours and the metabolite is excreted in the 6- to 48-hour period following administration. Renal clearance of propoxyphene is about 2.6 L/minute.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2197

    Formation of cytochrome p450 metabolic intermediate complexes in vivo occurred with propoxyphene in native & phenobarbital-induced rats. In vivo formation correlated with relative ability for it to form metabolic intermediate complexes & inhibit mixed function oxidation reactions in vitro.

    PMID:491835 ROBERTS SM, FRANKLIN MR; LIFE SCI 25 (10): 845-51 (1979)

    Yields 3-dimethylamino-1,2-diphenyl-2-butyl propionate-n-oxide iN pig & 3-methylamino-1,2-diphenyl-2-butyl propionate iN rat. From table/

    Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. D-83

    Presystemic metabolism is believed to occur mainly in the liver with some minor intestinal participation. The aim of this study was to investigate the respective part of each of these two organs in the metabolism of the analgesic d-propoxyphene. Pharmacological doses of d-propoxyphene were given in the duodenum (ID), the portal vein (IP), and the femoral vein (IV) of male Wistar rats. A tracer dose of (14)C-d-propoxyphene was also administered either in IV, IP, or ID as well as in hepatectomized rats or rats with bile duct diversion. In vitro demethylation occurring in liver and intestinal microsomes was also studied. Absolute DP bioavailability obtained after oral administration was two times higher than that observed after portal administration (48.9% vs. 23.2%, respectively), an result opposite (i.e. a lower bioavailability) of that expected on the basis of the existence of a liver enzyme saturation phenomenon. The (14)C-d-propoxyphene cumulative excretion after (14)C-d-propoxyphene administration was significantly lower after IV or ID administration than after injection in the portal vein as a bolus or within 20 min. The biliary excretion of the labeled compound varied in the opposite direction, being greater after IV or ID than after IP administration, suggesting that the metabolism of d-propoxyphene in the liver is influenced by an extrahepatic transformation. This most likely occurs in the gut since the production of (14)C-d-propoxyphene after IV administration was similar to that after ID administration. This transformation did not prohibit d-propoxyphene detection in the systemic blood but was sufficient to increase the part eliminated with bile and to decrease the part demethylated NP. Demethylation mainly occurs in the liver since the production of (14)C-d-propoxyphene was nearly abolished in hepatectomized rats. Furthermore, microsomes of hepatic but not of intestinal origin were able to demethylate d-propoxyphene. Our data suggest that the transformation of d-propoxyphene occurring in gut after oral administration is responsible for changes in the hepatic metabolism of the drug.

    PMID:9351901 Horsmans Y et al; Drug Metab Dispos 25 (11): 1257-9 (1997)

    Dextropropoxyphene has known human metabolites that include Nordextropropoxyphene.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    6-12 hours

    Propoxyphene has an elimination half-life of 6-12 hours.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2197

    The half life of elimination of the parent compound is 6 to 12 hours. The half life of elimination of norpropoxyphene is 30 to 36 hours.

    Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 773

    ... Norpropoxyphene has a longer plasma half-life in the dog than propoxyphene. /Propoxyphene hydrochloride/

    Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 291

    In geriatric patients 70-78 years of age, elimination half-lives of propoxyphene and norpropoxyphene reportedly were 13-35 and 22-41 hours, respectively.

    American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2198

    5.8 Mechanism of Action

    Propoxyphene acts as a weak agonist at OP1, OP2, and OP3 opiate receptors within the central nervous system (CNS). Propoxyphene primarily affects OP3 receptors, which are coupled with G-protein receptors and function as modulators, both positive and negative, of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine, and noradrenaline is inhibited. Opioids such as propoxyphene also inhibit the release of vasopressin, somatostatin, insulin, and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

    ... Propoxyphene binds primarily to mu-opioid receptors & produces analgesia & other CNS effects that are similar to those seen with morphine-like opioids.

    Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 11th ed. New York, NY: McGraw-Hill, 2006., p. 573

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