Oxymorphazone

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Oxymorphazone
Oxymorphazone.svg
Clinical data
SynonymsOxymorphone hydrazone
ATC code
  • none
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC17H21N3O3
Molar mass315.367 g/mol g·mol−1
3D model (JSmol)
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Oxymorphazone is an opioid analgesic drug related to oxymorphone. Oxymorphazone is a potent and long acting μ-opioid agonist which binds irreversibly to the receptor, forming a covalent bond which prevents it from detaching once bound.[1][2] This gives it an unusual pharmacological profile, and while oxymorphazone is only around half the potency of oxymorphone, with higher doses the analgesic effect becomes extremely long lasting, with a duration of up to 48 hours.[3] However, tolerance to analgesia develops rapidly with repeated doses,[4][5][6] as chronically activated opioid receptors are rapidly internalised by β-arrestins, similar to the results of non-covalent binding by repeated doses of agonists with extremely high binding affinity such as lofentanil.[7][8]

See also[edit]

References[edit]

  1. ^ Galetta S, Ling GS, Wolfin L, Pasternak GW. "Receptor binding and analgesic properties of oxymorphazone". Life Sciences. 31 (12–13): 1389–92. doi:10.1016/0024-3205(82)90388-5. PMID 6183551.
  2. ^ Hahn EF, Carroll-Buatti M, Pasternak GW (May 1982). "Irreversible opiate agonists and antagonists: the 14-hydroxydihydromorphinone azines". The Journal of Neuroscience. 2 (5): 572–6. PMID 6176696.
  3. ^ France CP, Jacobson AE, Woods JH (September 1984). "Discriminative stimulus effects of reversible and irreversible opiate agonists: morphine, oxymorphazone and buprenorphine". The Journal of Pharmacology and Experimental Therapeutics. 230 (3): 652–7. PMID 6206224.
  4. ^ Ling GS, Galetta S, Pasternak GW (March 1984). "Oxymorphazone: a long-acting opiate analgesic". Cellular and Molecular Neurobiology. 4 (1): 1–13. PMID 6204757.
  5. ^ Williams CL, Bodnar RJ, Clark JE, Hahn EF, Burks TF, Pasternak GW (April 1988). "Irreversible opiate agonists and antagonists. IV. Analgesic actions of 14-hydroxydihydromorphinone hydrazones". The Journal of Pharmacology and Experimental Therapeutics. 245 (1): 8–12. PMID 2452249.
  6. ^ Benyhe S, Hoffmann G, Varga E, Hosztafi S, Toth G, Borsodi A, Wollemann M. "Effects of oxymorphazone in frogs: long lasting antinociception in vivo, and apparently irreversible binding in vitro". Life Sciences. 44 (24): 1847–57. doi:10.1016/0024-3205(89)90302-0. PMID 2472540.
  7. ^ Marie N, Aguila B, Allouche S (November 2006). "Tracking the opioid receptors on the way of desensitization". Cellular Signalling. 18 (11): 1815–33. doi:10.1016/j.cellsig.2006.03.015. PMID 16750901.
  8. ^ DuPen A, Shen D, Ersek M (September 2007). "Mechanisms of opioid-induced tolerance and hyperalgesia". Pain Management Nursing. 8 (3): 113–21. doi:10.1016/j.pmn.2007.02.004. PMID 17723928.