Noroxycodone

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][5][4][7]

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
CompTox Dashboard (EPA)	DTXSID60973261
ECHA InfoCard	100.055.334
Chemical and physical data
Formula	C17H19NO4
Molar mass	301.342 g·mol^−1
3D model (JSmol)	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

See also

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

References

1. Smith H, Passik S (25 April 2008). Pain and Chemical Dependency. Oxford University Press, USA. pp. 195–. ISBN 978-0-19-530055-0.
2. McPherson RA, Pincus MR (31 March 2016). Henry's Clinical Diagnosis and Management by Laboratory Methods. Elsevier Health Sciences. pp. 336–. ISBN 978-0-323-41315-2.
3. Anzenbacher P, Zanger UM (29 May 2012). Metabolism of Drugs and Other Xenobiotics. John Wiley & Sons. pp. 420–. ISBN 978-3-527-32903-8.
4. Lemberg KK, Siiskonen AO, Kontinen VK, Yli-Kauhaluoma JT, Kalso EA (February 2008). "Pharmacological characterization of noroxymorphone as a new opioid for spinal analgesia". Anesthesia and Analgesia. 106 (2): 463–70, table of contents. doi:10.1213/ane.0b013e3181605a15. PMID 18227301.
5. Preedy VR (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, Liu-Chen LY, Shen DD (May 2006). "Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites". Clinical Pharmacology and Therapeutics. 79 (5): 461–79. doi:10.1016/j.clpt.2006.01.009. PMID 16678548.
7. Klimas R, Witticke D, El Fallah S, Mikus G (May 2013). "Contribution of oxycodone and its metabolites to the overall analgesic effect after oxycodone administration". Expert Opinion on Drug Metabolism & Toxicology. 9 (5): 517–28. doi:10.1517/17425255.2013.779669. PMID 23488585.