:8-Carboxamidocyclazocine

{{Short description|Opioid agonist drug}}

{{Drugbox

| verifiedrevid = 451607880

| IUPAC_name = (1S,10R,13R)-10-(Cyclopropylmethyl)-1,13-dimethyl-10-azatricyclo[7.3.1.0^2,7]trideca-2(7),3,5-triene-4-carboxamide

| image = 8-Carboxamidocyclazocine.svg

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

| CAS_number = 911207-68-6

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| PubChem = 10086063

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| ChemSpiderID = 30845204

| C=19 | H=26 | N=2 | O=1

| smiles = C[C@H]1[C@H]2Cc3ccc(cc3[C@]1(CCN2CC4CC4)C)C(=O)N

| StdInChI = 1S/C19H26N2O/c1-12-17-10-14-5-6-15(18(20)22)9-16(14)19(12,2)7-8-21(17)11-13-3-4-13/h5-6,9,12-13,17H,3-4,7-8,10-11H2,1-2H3,(H2,20,22)/t12-,17+,19-/m0/s1

| StdInChIKey = FAVQVALXVLMHLE-WILYLXEWSA-N

}}

8-Carboxamidocyclazocine (8-CAC) is an opioid analgesic drug related to cyclazocine, discovered by medicinal chemist Mark P. Wentland and co-workers in Cogswell Laboratory at Rensselaer Polytechnic Institute.US Patent 6784187 8-carboxamido-2,6-methano-3-benzazocines Similarly to cyclazocine, 8-CAC acts as an agonist at both the μ- and κ-opioid receptors, but has a much longer duration of action than cyclazocine, and does not have μ antagonist activity. Unexpectedly, it was discovered that the phenolic hydroxyl group of cyclazocine could be replaced by a carboxamido group with only slight loss of potency at opioid receptors, and this discovery has subsequently been used to develop many novel opioid derivatives where the phenolic hydroxy group has been replaced by either carboxamide or a variety of larger groups. Due to their strong κ-opioid agonist activity, these drugs are not suited for use as analgesics in humans, but have instead been researched as potential drugs for the treatment of cocaine addiction.{{cite journal | vauthors = Wentland MP, Lou R, Ye Y, Cohen DJ, Richardson GP, Bidlack JM | title = 8-Carboxamidocyclazocine analogues: redefining the structure-activity relationships of 2,6-methano-3-benzazocines | journal = Bioorganic & Medicinal Chemistry Letters | volume = 11 | issue = 5 | pages = 623–6 | date = March 2001 | pmid = 11266156 | doi = 10.1016/S0960-894X(01)00014-2 }}{{cite journal | vauthors = Bidlack JM, Cohen DJ, McLaughlin JP, Lou R, Ye Y, Wentland MP | s2cid = 15864569 | title = 8-Carboxamidocyclazocine: a long-acting, novel benzomorphan | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 302 | issue = 1 | pages = 374–80 | date = July 2002 | pmid = 12065740 | doi = 10.1124/jpet.302.1.374 }}{{cite journal | vauthors = Stevenson GW, Wentland MP, Bidlack JM, Mello NK, Negus SS | title = Effects of the mixed-action kappa/mu opioid agonist 8-carboxamidocyclazocine on cocaine- and food-maintained responding in rhesus monkeys | journal = European Journal of Pharmacology | volume = 506 | issue = 2 | pages = 133–41 | date = December 2004 | pmid = 15588733 | doi = 10.1016/j.ejphar.2004.10.051 }}{{cite journal | vauthors = Wentland MP, VanAlstine M, Kucejko R, Lou R, Cohen DJ, Parkhill AL, Bidlack JM | title = Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 4. Opioid receptor binding properties of 8-[N-(4'-phenyl)-phenethyl)carboxamido] analogues of cyclazocine and ethylketocycalzocine | journal = Journal of Medicinal Chemistry | volume = 49 | issue = 18 | pages = 5635–9 | date = September 2006 | pmid = 16942039 | doi = 10.1021/jm060278n }}{{cite journal | vauthors = VanAlstine MA, Wentland MP, Cohen DJ, Bidlack JM | title = Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. 5. Opioid receptor binding properties of N-((4'-phenyl)-phenethyl) analogues of 8-CAC | journal = Bioorganic & Medicinal Chemistry Letters | volume = 17 | issue = 23 | pages = 6516–20 | date = December 2007 | pmid = 17935988 | pmc = 2137165 | doi = 10.1016/j.bmcl.2007.09.082 }}{{cite journal | vauthors = Wentland MP, Sun X, Cohen DJ, Bidlack JM | title = Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 6: Opioid receptor binding properties of cyclic variants of 8-carboxamidocyclazocine | journal = Bioorganic & Medicinal Chemistry | volume = 16 | issue = 10 | pages = 5653–64 | date = May 2008 | pmid = 18417347 | pmc = 2441872 | doi = 10.1016/j.bmc.2008.03.066 }}{{cite journal | vauthors = Wentland MP, Lu Q, Ganorkar R, Zhang SZ, Jo S, Cohen DJ, Bidlack JM | title = Redefining the structure-activity relationships of 2,6-methano-3-benzazocines. Part 7: syntheses and opioid receptor properties of cyclic variants of cyclazocine | journal = Bioorganic & Medicinal Chemistry Letters | volume = 19 | issue = 2 | pages = 365–8 | date = January 2009 | pmid = 19091564 | doi = 10.1016/j.bmcl.2008.11.076 }}{{cite journal | vauthors = Wentland MP, Lou R, Lu Q, Bu Y, Denhardt C, Jin J, Ganorkar R, VanAlstine MA, Guo C, Cohen DJ, Bidlack JM | display-authors = 6 | title = Syntheses of novel high affinity ligands for opioid receptors | journal = Bioorganic & Medicinal Chemistry Letters | volume = 19 | issue = 8 | pages = 2289–94 | date = April 2009 | pmid = 19282177 | pmc = 2791460 | doi = 10.1016/j.bmcl.2009.02.078 }}{{cite journal | vauthors = Prisinzano TE, Tidgewell K, Harding WW | title = Kappa opioids as potential treatments for stimulant dependence | journal = The AAPS Journal | volume = 7 | issue = 3 | pages = E592-9 | date = October 2005 | pmid = 16353938 | pmc = 2751263 | doi = 10.1208/aapsj070361 }}