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Oxymorphazone

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From Wikipedia, the free encyclopedia

Opioid analgesic

Not to be confused withOxymorphone.

Pharmaceutical compound

Oxymorphazone
Clinical data


Other names	Oxymorphone hydrazone
ATC code	none
Identifiers
IUPAC name (5α,6E)-3,14-dihydroxy-17-methyl-4,5-epoxy-morphinan-6-one hydrazone
CAS Number	73697-35-5^Y
PubChemCID	9577748
ChemSpider	23231158
UNII	9J727K8R3U
Chemical and physical data
Formula	C₁₇H₂₁N₃O₃
Molar mass	315.373 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CC[C@]23[C@@H]4/C(=N/N)/CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O
InChI InChI=1S/C17H21N3O3/c1-20-7-6-16-13-9-2-3-11(21)14(13)23-15(16)10(19-18)4-5-17(16,22)12(20)8-9/h2-3,12,15,21-22H,4-8,18H2,1H3/b19-10-/t12-,15+,16+,17-/m1/s1 Key:VOFTYIFRRWVMOO-YKKXUTDFSA-N
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Oxymorphazone is anopioid analgesic drug related tooxymorphone. Oxymorphazone is a potent and long actingμ-opioid agonist which binds irreversibly to the receptor, forming acovalent 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 when administeredintraventricularly.^[3] However,tolerance to analgesia develops rapidly with repeated doses,^[4]^[5]^[6] as chronically activated opioid receptors are rapidlyinternalised byβ-arrestins, similar to the results of non-covalent binding by repeated doses of agonists with extremely highbinding affinity such aslofentanil.^[7]^[8]

References

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^Galetta S, Ling GS, Wolfin L, Pasternak GW (1982). "Receptor binding and analgesic properties of oxymorphazone".Life Sciences.31 (12–13):1389–92.doi:10.1016/0024-3205(82)90388-5.PMID 6183551.
^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.doi:10.1523/JNEUROSCI.02-05-00572.1982.PMC 6564265.PMID 6176696.
^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.doi:10.1016/S0022-3565(25)21704-9.PMID 6206224.
^Ling GS, Galetta S, Pasternak GW (March 1984)."Oxymorphazone: a long-acting opiate analgesic".Cellular and Molecular Neurobiology.4 (1):1–13.doi:10.1007/BF00710938.PMC 11572834.PMID 6204757.S2CID 30383345.
^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.doi:10.1016/S0022-3565(25)22279-0.PMID 2452249.
^Benyhe S, Hoffmann G, Varga E, Hosztafi S, Toth G, Borsodi A, Wollemann M (1989). "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.
^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.
^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.