Oxilorphan

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 Edit this at Wikidata
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 checkY
  • Key:STBZIDOIKQNFCQ-HSALFYBXSA-N checkY
  (verify)

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]

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.



This article is issued from Offline. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.