Oxilorphan

{{short description|Chemical compound}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 447991507

| IUPAC_name = (-)-17-(Cyclopropylmethyl)-morphinan-3,14-diol

| image = Oxilorphan.svg

| image_class = skin-invert-image

| width = 140

| tradename =

| pregnancy_category =

| legal_status =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 42281-59-4

| ATC_prefix = None

| ATC_suffix =

| PubChem = 5361090

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16736680

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 9Y9J2J74TO

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D05299

| C=20 | H=27 | N=1 | O=2

| smiles = Oc3ccc4C[C@H]1N(CC[C@@]2(CCCC[C@@]12O)c4c3)CC5CC5

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = STBZIDOIKQNFCQ-HSALFYBXSA-N

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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.{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA916|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=916–}} 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.{{cite journal | vauthors = Pircio AW, Gylys JA | title = Oxilorphan (l-N-cyclopropylmethyl-3,14-dihydroxymorphinan): a new synthetic narcotic antagonist | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 193 | issue = 1 | pages = 23–34 | date = April 1975 | doi = 10.1016/S0022-3565(25)30118-7 | pmid = 237112 }} Oxilorphan has some weak partial agonist actions at the MOR (with miosis, nausea, dizziness, and some euphoria observed){{cite journal | vauthors = Sellers EM, Thakur R | title = Partial agonist properties and toxicity of oral oxilorphan | journal = Journal of Clinical Pharmacology | volume = 16 | issue = 4 | pages = 183–7 | date = April 1976 | pmid = 4472 | doi = 10.1002/j.1552-4604.1976.tb01515.x | s2cid = 2819499 }}{{cite book | vauthors = Gordon M |title=Annual Reports in Medicinal Chemistry |volume = 9 | chapter = Abuse of CNS Agents | chapter-url=https://books.google.com/books?id=rZBH1_7Tx6UC&pg=PA41|date=22 November 1974|publisher=Academic Press|isbn=978-0-08-058353-2|pages=41–}} and can produce hallucinogenic/dissociative effects at sufficient doses, indicative of KOR activation.{{cite journal | vauthors = Leander JD | title = Evidence that nalorphine, butorphanol and oxilorphan are partial agonists at a kappa-opioid receptor | journal = European Journal of Pharmacology | volume = 86 | issue = 3–4 | pages = 467–70 | date = January 1983 | pmid = 6131829 | doi = 10.1016/0014-2999(83)90198-x }} It was trialed for the treatment of opioid addiction, but was not developed commercially.{{cite journal | vauthors = Tennant FS, Tate JA, Ruckel E | title = Clinical trial in post-addicts with oxilorphan (levo-BC-2605): a new narcotic antagonist | journal = Drug and Alcohol Dependence | volume = 1 | issue = 5 | pages = 329–37 | date = June 1976 | pmid = 13984 | doi = 10.1016/0376-8716(76)90035-1 }} 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.{{cite book|author=National Research Council (U.S.). Committee on Problems of Drug Dependence|title=Problems of drug dependence|url=https://books.google.com/books?id=3aEeAQAAMAAJ|year=1975|publisher=National Academy of Sciences.|isbn=9780309024174}}