Noroxycodone

Noroxycodone

Identifiers
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
CAS Number	57664-96-7
PubChem (CID)	5489120
ChemSpider	4590081
UNII	95Q949779D
Chemical and physical data
Formula	C17H19NO4
Molar mass	301.34 g·mol^−1
3D model (Jmol)	Interactive image
SMILES COC1=C2C3=C(C[C@@H]4[C@]5([C@]3(CCN4)[C@@H](O2)C(=O)CC5)O)C=C1
InChI InChI=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 Key:RIKMCJUNPCRFMW-ISWURRPUSA-N

Noroxycodone is the major metabolite of the opioid analgesic oxycodone.^[1][2][3] It is formed from oxycodone in the liver via N-demethylation predominantly by CYP3A4.^[1][2][3] 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.^[1][4][5] 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.^[6]<ref name="Preedy2016" /^[4][7]

See also

• Norbuprenorphine
• Norbuprenorphine-3-glucuronide
• Norhydrocodone
• Normorphine
• Noroxymorphone

References

1. Howard Smith; Steven Passik (25 April 2008). Pain and Chemical Dependency. Oxford University Press, USA. pp. 195–. ISBN 978-0-19-530055-0.
2. Richard A. McPherson; Matthew R. Pincus (31 March 2016). Henry's Clinical Diagnosis and Management by Laboratory Methods. Elsevier Health Sciences. pp. 336–. ISBN 978-0-323-41315-2.
3. Pavel Anzenbacher; Ulrich M. Zanger (29 May 2012). Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. pp. 420–. ISBN 978-3-527-32903-8.
4. Lemberg, Kim K.; Siiskonen, Antti O.; Kontinen, Vesa K.; Yli-Kauhaluoma, Jari T.; Kalso, Eija A. (2008). "Pharmacological Characterization of Noroxymorphone as a New Opioid for Spinal Analgesia". Anesthesia & Analgesia. 106 (2): 463–470. doi:10.1213/ane.0b013e3181605a15. ISSN 0003-2999.
5. Victor R. Preedy (25 April 2016). 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. Elsevier Science. pp. 462–464. ISBN 978-0-12-800677-1.
6. Lalovic, B; Kharasch, E; Hoffer, C; Risler, L; Liuchen, L; Shen, D (2006). "Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: Role of circulating active metabolites". Clinical Pharmacology & Therapeutics. 79 (5): 461–479. doi:10.1016/j.clpt.2006.01.009. ISSN 0009-9236.
7. Klimas, Romina; Witticke, Diana; El Fallah, Sarah; Mikus, Gerd (2013). "Contribution of oxycodone and its metabolites to the overall analgesic effect after oxycodone administration". Expert Opinion on Drug Metabolism & Toxicology. 9 (5): 517–528. doi:10.1517/17425255.2013.779669. ISSN 1742-5255.