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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ECHA InfoCard100.050.664
Chemical and physical data
FormulaC20H27NO2
Molar mass313.44 g/mol g·mol−1
3D model (JSmol)
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See also

References
  1. J. Elks (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. Oxilorphan (l-N-cyclopropylmethyl-3,14-dihydroxymorphinan): a new synthetic narcotic antagonist. Journal of Pharmacology and Experimental Therapeutics. 1975 Apr;193(1):23-34.
  3. Sellers EM, Thakur R. Partial agonist properties and toxicity of oral oxilorphan. Journal of Clinical Pharmacology. 1976 Apr;16(4):183-7.
  4. ANNUAL REPORTS IN MED CHEMISTRY V9 PPR. Academic Press. 22 November 1974. pp. 41–. ISBN 978-0-08-058353-2.
  5. Leander JD. Evidence that nalorphine, butorphanol and oxilorphan are partial agonists at a kappa-opioid receptor. European Journal of Pharmacology. 1983 Jan 21;86(3-4):467-70.
  6. Tennant FS Jr, Tate JA, Ruckel E. Clinical trial in post-addicts with oxilorphan (levo-BC-2605): a new narcotic antagonist. Drug and Alcohol Dependence. 1976 Jun;1(5):329-37.
  7. National Research Council (U.S.). Committee on Problems of Drug Dependence (1975). Problems of drug dependence. National Academy of Sciences.



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