Oxilorphan

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Oxilorphan
Oxilorphan.svg
Systematic (IUPAC) name
(-)-17-(Cyclopropylmethyl)-morphinan-3,14-diol
Identifiers
CAS Number 42281-59-4 YesY
ATC code None
PubChem CID: 5361090
ChemSpider 16736680 YesY
UNII 9Y9J2J74TO YesY
KEGG D05299 YesY
Chemical data
Formula C20H27NO2
Molecular mass 313.44 g/mol
  • Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@]12O)c4c3)CC5CC5
  • 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 YesY
  • Key:STBZIDOIKQNFCQ-HSALFYBXSA-N YesY
  (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

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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