noroxycodone

{{Short description|Chemical compound}}

{{Drugbox

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| IUPAC_name = (4R,4aS,7aR,12bS)-4a-Hydroxy-9-methoxy-1,2,3,4,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one

| image = Noroxycodone.svg

| width = 200px

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| dependency_liability = High (same oxycodone)

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| CAS_number_Ref =

| CAS_number = 57664-96-7

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| PubChem = 5489120

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| ChemSpiderID_Ref =

| ChemSpiderID = 4590081

| UNII = 95Q949779D

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| C = 17

| H = 19

| N = 1

| O = 4

| smiles = COC1=C2C3=C(C[C@@H]4[C@]5([C@]3(CCN4)[C@@H](O2)C(=O)CC5)O)C=C1

| StdInChI_Ref =

| StdInChI = 1S/C17H19NO4/c1-21-11-3-2-9-8-12-17(20)5-4-10(19)15-16(17,6-7-18-12)13(9)14(11)22-15/h2-3,12,15,18,20H,4-8H2,1H3/t12-,15+,16+,17-/m1/s1

| StdInChIKey_Ref =

| StdInChIKey = RIKMCJUNPCRFMW-ISWURRPUSA-N

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}}

Noroxycodone is the major metabolite of the opioid analgesic oxycodone.{{cite book| vauthors = Smith HS, Vanderah TW, McClean G | chapter = Opioids for Pain | veditors = Smith H, Passik S |title=Pain and Chemical Dependency| chapter-url= https://books.google.com/books?id=T88C-9VTDXMC&pg=PA195|date=25 April 2008|publisher=Oxford University Press, USA|isbn=978-0-19-530055-0|pages=195–}}{{cite book| vauthors = Pincus MR, Bluth MH, Abraham Jr NZ | chapter = Toxicology and Therapeutic Drug Monitoring | veditors = McPherson RA, Pincus MR |title=Henry's Clinical Diagnosis and Management by Laboratory Methods | chapter-url= https://books.google.com/books?id=xAzhCwAAQBAJ&pg=PA336|date=31 March 2016|publisher=Elsevier Health Sciences|isbn=978-0-323-41315-2|pages=336–}}{{cite book| vauthors = Somogyi AA, Coller JK | chapter = Drugs against Acute and Chronic Pain | veditors = Anzenbacher P, Zanger UM |title=Metabolism of Drugs and Other Xenobiotics| chapter-url=https://books.google.com/books?id=ulcB7zYIresC&pg=PA420|date=29 May 2012|publisher=John Wiley & Sons|isbn=978-3-527-32903-8|pages=420–}} It is formed from oxycodone in the liver via N-demethylation predominantly by CYP3A4. Noroxycodone binds to and activates the μ-opioid receptor (MOR) similarly to oxycodone, although with one-third of the affinity of oxycodone and 5- to 10-fold lower activational potency.{{cite journal | vauthors = Lemberg KK, Siiskonen AO, Kontinen VK, Yli-Kauhaluoma JT, Kalso EA | title = Pharmacological characterization of noroxymorphone as a new opioid for spinal analgesia | journal = Anesthesia and Analgesia | volume = 106 | issue = 2 | pages = 463–70, table of contents | date = February 2008 | pmid = 18227301 | doi = 10.1213/ane.0b013e3181605a15 | s2cid = 16524280 | doi-access = free }}{{cite book| vauthors = Kokki H, Kokki M | chapter = Central Nervous System Penetration of the Opioid Oxycodone | veditors = Preedy VR |title=Neuropathology of Drug Addictions and Substance Misuse Volume 3: General Processes and Mechanisms, Prescription Medications, Caffeine and Areca, Polydrug Misuse, Emerging Addictions and Non-Drug Addictions| chapter-url = https://books.google.com/books?id=Yu9eBwAAQBAJ&pg=PA462|date=25 April 2016|publisher=Elsevier Science|isbn=978-0-12-800677-1|pages=462–464}} However, although a potent MOR agonist, noroxycodone poorly crosses the blood-brain-barrier into the central nervous system, and for this reason, is only minimally analgesic in comparison.{{cite journal | vauthors = Lalovic B, Kharasch E, Hoffer C, Risler L, Liu-Chen LY, Shen DD | title = Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites | journal = Clinical Pharmacology and Therapeutics | volume = 79 | issue = 5 | pages = 461–479 | date = May 2006 | pmid = 16678548 | doi = 10.1016/j.clpt.2006.01.009 | s2cid = 21372271 }}{{cite journal | vauthors = Klimas R, Witticke D, El Fallah S, Mikus G | title = Contribution of oxycodone and its metabolites to the overall analgesic effect after oxycodone administration | journal = Expert Opinion on Drug Metabolism & Toxicology | volume = 9 | issue = 5 | pages = 517–528 | date = May 2013 | pmid = 23488585 | doi = 10.1517/17425255.2013.779669 | s2cid = 22857902 }}