Oxymorphazone

Not to be confused with Oxymorphone.

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]

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
PubChem CID	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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See also

• Chlornaltrexamine, an irreversible mixed μ-opioid agonist-antagonist
• Chloroxymorphamine, another irreversible μ-opioid full agonist
• Naloxazone, an irreversible μ-opioid antagonist