Oxymorphazone

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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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. 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. However, tolerance to analgesia develops rapidly with repeated doses, 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.

See also

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