Oxymorphazone
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Oxymorphazone
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|---|---|
| Systematic (IUPAC) name | |
| (5α,6E)- 3,14-dihydroxy- 17-methyl- 4,5-epoxy- morphinan- 6-one hydrazone | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 73697-35-5 |
| ATC code | None |
| PubChem | CID 9577748 |
| Synonyms | Oxymorphone hydrazone |
| Chemical data | |
| Formula | C17H21N3O3 |
| Mol. mass | 315.367 g/mol |
| SMILES | eMolecules & PubChem |
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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 agonists with extremely high binding affinity such as lofentanil.[7][8]
See also
- Chlornaltrexamine, an irreversible mixed agonist-antagonist
- Naloxazone, an irreversible μ-opioid antagonist
References
- ^ Galetta S, Ling GS, Wolfin L, Pasternak GW. Receptor binding and analgesic properties of oxymorphazone. Life Sciences. 1982 Sep 20-27;31(12-13):1389-92. PMID 6183551
- ^ Hahn EF, Carroll-Buatti M, Pasternak GW. Irreversible opiate agonists and antagonists: the 14-hydroxydihydromorphinone azines. Journal of Neuroscience. 1982 May;2(5):572-6. PMID 6176696
- ^ France CP, Jacobson AE, Woods JH. Discriminative stimulus effects of reversible and irreversible opiate agonists: morphine, oxymorphazone and buprenorphine. Journal of Pharmacology and Experimental Therapeutics. 1984 Sep;230(3):652-7. PMID 6206224
- ^ Ling GS, Galetta S, Pasternak GW. Oxymorphazone: a long-acting opiate analgesic. Cellular and Molecular Neurobiology. 1984 Mar;4(1):1-13. PMID 6204757
- ^ Williams CL, Bodnar RJ, Clark JE, Hahn EF, Burks TF, Pasternak GW. Irreversible opiate agonists and antagonists. IV. Analgesic actions of 14-hydroxydihydromorphinone hydrazones. Journal of Pharmacology and Experimental Therapeutics. 1988 Apr;245(1):8-12. PMID 2452249
- ^ 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. 1989;44(24):1847-57. PMID 2472540
- ^ Marie N, Aguila B, Allouche S. Tracking the opioid receptors on the way of desensitization. Cellular Signalling. 2006 Nov;18(11):1815-33. doi:10.1016/j.cellsig.2006.03.015 PMID 16750901
- ^ DuPen A, Shen D, Ersek M. Mechanisms of opioid-induced tolerance and hyperalgesia. Pain Management Nursing. 2007 Sep;8(3):113-21. doi:10.1016/j.pmn.2007.02.004 PMID 17723928
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