| Revision as of 19:30, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 447739013 of page ABT-239 for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:37, 1 May 2023 edit RaydenAG (talk | contribs)Extended confirmed users699 editsmNo edit summary |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Drugbox |
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{{Drugbox |
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| verifiedrevid = 413288200 |
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| verifiedrevid = 477235076 |
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| IUPAC_name = 4-(2-{2-ethyl}-<br>benzofuran-5-yl)benzonitrile |
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| IUPAC_name = 4-(2-{2-ethyl}-<br>benzofuran-5-yl)benzonitrile |
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| image = ABT-239.svg |
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| image = ABT-239.svg |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number = 460746-46-7 |
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| CAS_supplemental = <BR>460746-51-4 (racemic)<BR>460749-29-5 (''S''-isomer) |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 86H6B395PI |
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| IUPHAR_ligand = 1218 |
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| PubChem = 9818903 |
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| PubChem = 9818903 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 351231 |
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| ChEMBL = 351231 |
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<!-- Pharmacokinetic data --> |
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| bioavailability = |
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| protein_bound = |
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| metabolism = |
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| metabolites = |
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| onset = |
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| elimination_half-life = |
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| duration_of_action = |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=22 | H=22 | N=2 | O=1 |
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| C=22 | H=22 | N=2 | O=1 |
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| smiles = N#CC1=CC=C(C2=CC3=C(C=C2)OC(CCN4(CCC4)C)=C3)C=C1 |
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| molecular_weight = 330.42 g/mol |
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| smiles = N#Cc4ccc(c3cc1c(oc(c1)CCN2(C)CCC2)cc3)cc4 |
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| InChI = 1/C22H22N2O/c1-16-3-2-11-24(16)12-10-21-14-20-13-19(8-9-22(20)25-21)18-6-4-17(15-23)5-7-18/h4-9,13-14,16H,2-3,10-12H2,1H3/t16-/m1/s1 |
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| InChIKey = KFHYZKCRXNRKRC-MRXNPFEDBU |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C22H22N2O/c1-16-3-2-11-24(16)12-10-21-14-20-13-19(8-9-22(20)25-21)18-6-4-17(15-23)5-7-18/h4-9,13-14,16H,2-3,10-12H2,1H3/t16-/m1/s1 |
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| StdInChI = 1S/C22H22N2O/c1-16-3-2-11-24(16)12-10-21-14-20-13-19(8-9-22(20)25-21)18-6-4-17(15-23)5-7-18/h4-9,13-14,16H,2-3,10-12H2,1H3/t16-/m1/s1 |
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| StdInChIKey = KFHYZKCRXNRKRC-MRXNPFEDSA-N |
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| StdInChIKey = KFHYZKCRXNRKRC-MRXNPFEDSA-N |
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}} |
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'''ABT-239''' is an ] ] developed by ]. It has ] and ] effects, and has been investigated as a treatment for ], ], and ].<ref name="pmid15608078">{{cite journal |vauthors=Esbenshade TA, Fox GB, Krueger KM, Miller TR, Kang CH, Denny LI, Witte DG, Yao BB, Pan L, Wetter J, Marsh K, Bennani YL, Cowart MD, Sullivan JP, Hancock AA | title = Pharmacological properties of ABT-239 ethyl}-benzofuran-5-yl)benzonitrile]: I. Potent and selective histamine H<sub>3</sub> receptor antagonist with drug-like properties | journal = J. Pharmacol. Exp. Ther. | volume = 313 | issue = 1 | pages = 165–75 | year = 2005 | pmid = 15608078 | doi = 10.1124/jpet.104.078303 | s2cid = 573355 }}</ref><ref name="pmid15608077">{{cite journal |vauthors=Fox GB, Esbenshade TA, Pan JB, Radek RJ, Krueger KM, Yao BB, Browman KE, Buckley MJ, Ballard ME, Komater VA, Miner H, Zhang M, Faghih R, Rueter LE, Bitner RS, Drescher KU, Wetter J, Marsh K, Lemaire M, Porsolt RD, Bennani YL, Sullivan JP, Cowart MD, Decker MW, Hancock AA | title = Pharmacological properties of ABT-239 ethyl}-benzofuran-5-yl)benzonitrile]: II. Neurophysiological characterization and broad preclinical efficacy in cognition and schizophrenia of a potent and selective histamine H<sub>3</sub> receptor antagonist | journal = J. Pharmacol. Exp. Ther. | volume = 313 | issue = 1 | pages = 176–90 | year = 2005 | pmid = 15608077 | doi = 10.1124/jpet.104.078402 | s2cid = 15430117 }}</ref><ref name="pmid15634000">{{cite journal |vauthors=Cowart M, Faghih R, Curtis MP, Gfesser GA, Bennani YL, Black LA, Pan L, Marsh KC, Sullivan JP, Esbenshade TA, Fox GB, Hancock AA | title = 4-(2-benzofuran-5-yl)benzonitrile and related 2-aminoethylbenzofuran H<sub>3</sub> receptor antagonists potently enhance cognition and attention | journal = J. Med. Chem. | volume = 48 | issue = 1 | pages = 38–55 | year = 2005 | pmid = 15634000 | doi = 10.1021/jm040118g }}</ref><ref name="pmid18305012">{{cite journal |vauthors=Le S, Gruner JA, Mathiasen JR, Marino MJ, Schaffhauser H | title = Correlation between ''ex vivo'' receptor occupancy and wake-promoting activity of selective H<sub>3</sub> receptor antagonists | journal = J. Pharmacol. Exp. Ther. | volume = 325 | issue = 3 | pages = 902–9 |date=June 2008 | pmid = 18305012 | doi = 10.1124/jpet.107.135343 | s2cid = 26536000 }}</ref> ABT-239 is more active at the human H<sub>3</sub> receptor than comparable agents such as ], ], and ]. It was ultimately dropped from human trials after showing the dangerous cardiac side effect of ],<ref>{{cite journal | last1 = Hancock | first1 = AA | title = The challenge of drug discovery of a GPCR target: analysis of preclinical pharmacology of histamine H3 antagonists/inverse agonists. | journal = ] | volume = 71 | issue = 8 | pages = 1103–13 | year = 2006 | pmid = 16513092 | doi = 10.1016/j.bcp.2005.10.033 }}</ref> but is still widely used in animal research into H<sub>3</sub> antagonists / inverse agonists. |
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==References== |
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{{Reflist|2}} |
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==External links== |
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* {{MeshName|4-(2-(2-(2-methyl-1-pyrrolidinyl)ethyl)-1-benzofuran-5-yl)benzonitrile}} |
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{{Histaminergics}} |
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{{DEFAULTSORT:Abt-239}} |
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{{nervous-system-drug-stub}} |