Noroxycodone

{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = | Watchedfields = | verifiedrevid = | IUPAC_name = (4''R'',4a''S'',7a''R'',12b''S'')-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 | image_class = skin-invert-image | width = 200px

| tradename = | pregnancy_AU =  | pregnancy_US =  | pregnancy_category = | legal_AU =  | legal_CA = | legal_UK = | legal_US = | legal_status = | dependency_liability = High (same oxycodone) | routes_of_administration =  | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =  | CAS_number_Ref = | CAS_number = 57664-96-7 | CAS_supplemental = | ATC_prefix = | ATC_suffix = | ATC_supplemental = | PubChem = 5489120 | IUPHAR_ligand = | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 4590081 | UNII = 95Q949779D | KEGG = | ChEBI = | ChEMBL =  | 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 | synonyms = }}

'''Noroxycodone''' is the major metabolite of the opioid analgesic oxycodone.<ref name="SmithPassik2008">{{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–}}</ref><ref name="McPhersonPincus2016">{{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–}}</ref><ref name="AnzenbacherZanger2012">{{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–}}</ref> It is formed from oxycodone in the liver via N-demethylation predominantly by CYP3A4.<ref name="SmithPassik2008" /><ref name="McPhersonPincus2016" /><ref name="AnzenbacherZanger2012" /> 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.<ref name="SmithPassik2008" /><ref name="LembergSiiskonen2008">{{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 }}</ref><ref name="Preedy2016">{{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}}</ref> 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.<ref name="LalovicKharasch2006">{{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 }}</ref><ref name="Preedy2016" /><ref name="LembergSiiskonen2008" /><ref name="KlimasWitticke2013">{{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 }}</ref>

== References == {{Reflist|2}}

Category:4,5-Epoxymorphinans Category:Ketones Category:Opioid metabolites

{{analgesic-stub}} Category:Recreational drug metabolites