Chemistry:Oxilorphan
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| Formula | C20H27NO2 |
| Molar mass | 313.441 g·mol−1 |
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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
- Butorphanol
- Cyclorphan
- Ketorfanol
- Levallorphan
- Levomethorphan
- Levorphanol
- Nalbuphine
- Proxorphan
- Xorphanol
References
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 916–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA916.
- ↑ "Oxilorphan (l-N-cyclopropylmethyl-3,14-dihydroxymorphinan): a new synthetic narcotic antagonist". The Journal of Pharmacology and Experimental Therapeutics 193 (1): 23–34. April 1975. PMID 237112.
- ↑ "Partial agonist properties and toxicity of oral oxilorphan". Journal of Clinical Pharmacology 16 (4): 183–7. April 1976. doi:10.1002/j.1552-4604.1976.tb01515.x. PMID 4472.
- ↑ "Abuse of CNS Agents". Annual Reports in Medicinal Chemistry. 9. Academic Press. 22 November 1974. pp. 41–. ISBN 978-0-08-058353-2. https://books.google.com/books?id=rZBH1_7Tx6UC&pg=PA41.
- ↑ "Evidence that nalorphine, butorphanol and oxilorphan are partial agonists at a kappa-opioid receptor". European Journal of Pharmacology 86 (3–4): 467–70. January 1983. doi:10.1016/0014-2999(83)90198-x. PMID 6131829.
- ↑ "Clinical trial in post-addicts with oxilorphan (levo-BC-2605): a new narcotic antagonist". Drug and Alcohol Dependence 1 (5): 329–37. June 1976. doi:10.1016/0376-8716(76)90035-1. PMID 13984.
- ↑ National Research Council (U.S.). Committee on Problems of Drug Dependence (1975). Problems of drug dependence. National Academy of Sciences.. ISBN 9780309024174. https://books.google.com/books?id=3aEeAQAAMAAJ.
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