Oxilorphan

Oxilorphan (INN, USAN) (developmental code name L-BC-2605) is an opioid antagonist of the morphinan family that was never marketed.[1] It acts as a μ-opioid receptor (MOR) antagonist but a κ-opioid receptor (KOR) partial agonist, and has similar effects to naloxone and around the same potency as an MOR antagonist.[2] Oxilorphan has some weak partial agonist actions at the MOR (with miosis, nausea, dizziness, and some euphoria observed)[3][4] and can produce hallucinogenic/dissociative effects at sufficient doses, indicative of KOR activation.[5] It was trialed for the treatment of opioid addiction, but was not developed commercially.[6] The KOR agonist effects of oxilorphan are associated with dysphoria, which combined with its hallucinogenic effects, serve to limit its clinical usefulness; indeed, many patients who experienced these side effects refused to take additional doses in clinical trials.[7]

Oxilorphan
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • (-)-17-(Cyclopropylmethyl)-morphinan-3,14-diol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.050.664
Chemical and physical data
FormulaC20H27NO2
Molar mass313.441 g·mol−1
3D model (JSmol)
SMILES
  • Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@]12O)c4c3)CC5CC5
InChI
  • InChI=1S/C20H27NO2/c22-16-6-5-15-11-18-20(23)8-2-1-7-19(20,17(15)12-16)9-10-21(18)13-14-3-4-14/h5-6,12,14,18,22-23H,1-4,7-11,13H2/t18-,19+,20-/m1/s1 Y
  • Key:STBZIDOIKQNFCQ-HSALFYBXSA-N Y
  (verify)

See also

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 916–. ISBN 978-1-4757-2085-3.
  2. Pircio AW, Gylys JA (April 1975). "Oxilorphan (l-N-cyclopropylmethyl-3,14-dihydroxymorphinan): a new synthetic narcotic antagonist". The Journal of Pharmacology and Experimental Therapeutics. 193 (1): 23–34. PMID 237112.
  3. Sellers EM, Thakur R (April 1976). "Partial agonist properties and toxicity of oral oxilorphan". Journal of Clinical Pharmacology. 16 (4): 183–7. doi:10.1002/j.1552-4604.1976.tb01515.x. PMID 4472. S2CID 2819499.
  4. Gordon M (22 November 1974). "Abuse of CNS Agents". Annual Reports in Medicinal Chemistry. Vol. 9. Academic Press. pp. 41–. ISBN 978-0-08-058353-2.
  5. Leander JD (January 1983). "Evidence that nalorphine, butorphanol and oxilorphan are partial agonists at a kappa-opioid receptor". European Journal of Pharmacology. 86 (3–4): 467–70. doi:10.1016/0014-2999(83)90198-x. PMID 6131829.
  6. Tennant FS, Tate JA, Ruckel E (June 1976). "Clinical trial in post-addicts with oxilorphan (levo-BC-2605): a new narcotic antagonist". Drug and Alcohol Dependence. 1 (5): 329–37. doi:10.1016/0376-8716(76)90035-1. PMID 13984.
  7. National Research Council (U.S.). Committee on Problems of Drug Dependence (1975). Problems of drug dependence. National Academy of Sciences. ISBN 9780309024174.



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