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Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and ABT-418: Difference between pages

(Difference between pages)
Content deleted Content added
Saving copy of the {{drugbox}} taken from revid 448114870 of page ABT-418 for the Chem/Drugbox validation project (updated: 'CAS_number').
 
IB autocalculates MW
 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid [{{fullurl:ABT-418|oldid=448114870}} 448114870] of page [[ABT-418]] with values updated to verified values.}}
{{cs1 config|name-list-style=vanc}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 413288284
| Watchedfields = changed
| IUPAC_name = 3-methyl-5-[(2S)-1-methylpyrrolidin-2-yl]-1,2-oxazole
| verifiedrevid =
| image = ABT-418.png
| IUPAC_name = 3--5-[()-1-methylpyrrolidin-2-yl]-1,2-oxazole
| width = 240
| image = ABT-418.
| width =


<!--Clinical data-->
<!--Clinical data-->
| tradename =
| tradename =
| routes_of_administration =
| routes_of_administration =


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 147402-53-7 -->
| CAS_number = 147402-53-7
| ATC_suffix =
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B9I6MZL7BW
| ATC_suffix =
| PubChem = 119380
| PubChem = 119380
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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<!--Chemical data-->
<!--Chemical data-->
| C=9 | H=14 | N=2 | O=1
| C=9 | H=14 | N=2 | O=1
| molecular_weight = 166.22
| smiles = CC1=NOC(=C1)[C@@H]2CCCN2C
| smiles = CC1=NOC(=C1)[C@@H]2CCCN2C
| InChI = 1/C9H14N2O/c1-7-6-9(12-10-7)8-4-3-5-11(8)2/h6,8H,3-5H2,1-2H3/t8-/m0/s1
| InChIKey = ILLGYRJAYAAAEW-QMMMGPOBBM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H14N2O/c1-7-6-9(12-10-7)8-4-3-5-11(8)2/h6,8H,3-5H2,1-2H3/t8-/m0/s1
| StdInChI = 1S/C9H14N2O/c1-7-6-9(12-10-7)8-4-3-5-11(8)2/h6,8H,3-5H2,1-2H3/t8-/m0/s1
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| StdInChIKey = ILLGYRJAYAAAEW-QMMMGPOBSA-N
| StdInChIKey = ILLGYRJAYAAAEW-QMMMGPOBSA-N
}}
}}

'''ABT-418''' is a drug developed by [[Abbott Laboratories|Abbott]], that has [[nootropic]], [[neuroprotective]] and [[anxiolytic]] effects,<ref name="pmid7518514">{{cite journal | vauthors = Arneric SP, Sullivan JP, Briggs CA, Donnelly-Roberts D, Anderson DJ, Raszkiewicz JL, Hughes ML, Cadman ED, Adams P, Garvey DS | display-authors = 6 | title = (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl) isoxazole (ABT 418): a novel cholinergic ligand with cognition-enhancing and anxiolytic activities: I. In vitro characterization | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 270 | issue = 1 | pages = 310–318 | date = July 1994 | pmid = 7518514 | url = http://jpet.aspetjournals.org/cgi/content/abstract/270/1/310 }}</ref><ref name="pmid7913497">{{cite journal | vauthors = Decker MW, Brioni JD, Sullivan JP, Buckley MJ, Radek RJ, Raszkiewicz JL, Kang CH, Kim DJ, Giardina WJ, Wasicak JT | display-authors = 6 | title = (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole (ABT 418): a novel cholinergic ligand with cognition-enhancing and anxiolytic activities: II. In vivo characterization | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 270 | issue = 1 | pages = 319–328 | date = July 1994 | pmid = 7913497 | url = http://jpet.aspetjournals.org/cgi/content/abstract/270/1/319 }}</ref><ref name="pmid7965735">{{cite journal | vauthors = Brioni JD, O'Neill AB, Kim DJ, Buckley MJ, Decker MW, Arneric SP | title = Anxiolytic-like effects of the novel cholinergic channel activator ABT-418 | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 271 | issue = 1 | pages = 353–361 | date = October 1994 | pmid = 7965735 | url = http://jpet.aspetjournals.org/cgi/reprint/271/1/353 }}</ref><ref name="pmid9151363">{{cite journal | vauthors = Prendergast MA, Terry AV, Jackson WJ, Marsh KC, Decker MW, Arneric SP, Buccafusco JJ | title = Improvement in accuracy of delayed recall in aged and non-aged, mature monkeys after intramuscular or transdermal administration of the CNS nicotinic receptor agonist ABT-418 | journal = Psychopharmacology | volume = 130 | issue = 3 | pages = 276–284 | date = April 1997 | pmid = 9151363 | doi = 10.1007/s002130050240 | s2cid = 34377165 }}</ref><ref>{{cite journal | vauthors = Dallanoce C, Magrone P, Matera C, Lo Presti L, De Amici M, Riganti L, Clementi F, Gotti C, De Micheli C | display-authors = 6 | title = Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes | journal = European Journal of Medicinal Chemistry | volume = 45 | issue = 12 | pages = 5594–5601 | date = December 2010 | pmid = 20932609 | doi = 10.1016/j.ejmech.2010.09.009 }}</ref> and has been researched for treatment of both [[Alzheimer's disease]]<ref name="pmid10229057">{{cite journal | vauthors = Potter A, Corwin J, Lang J, Piasecki M, Lenox R, Newhouse PA | title = Acute effects of the selective cholinergic channel activator (nicotinic agonist) ABT-418 in Alzheimer's disease | journal = Psychopharmacology | volume = 142 | issue = 4 | pages = 334–342 | date = March 1999 | pmid = 10229057 | doi = 10.1007/s002130050897 | s2cid = 27337634 }}</ref> and [[ADHD]].<ref name="pmid10588407">{{cite journal | vauthors = Wilens TE, Biederman J, Spencer TJ, Bostic J, Prince J, Monuteaux MC, Soriano J, Fine C, Abrams A, Rater M, Polisner D | display-authors = 6 | title = A pilot controlled clinical trial of ABT-418, a cholinergic agonist, in the treatment of adults with attention deficit hyperactivity disorder | journal = The American Journal of Psychiatry | volume = 156 | issue = 12 | pages = 1931–1937 | date = December 1999 | pmid = 10588407 | doi = 10.1176/ajp.156.12.1931 | s2cid = 20375475 }}</ref><ref name="pmid11336608">{{cite journal | vauthors = Horrigan JP | title = Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder | journal = Expert Opinion on Pharmacotherapy | volume = 2 | issue = 4 | pages = 573–586 | date = April 2001 | pmid = 11336608 | doi = 10.1517/14656566.2.4.573 | s2cid = 41914443 }}</ref><ref name="pmid12685525">{{cite journal | vauthors = Spencer T, Biederman J | title = Non-stimulant treatment for Attention-Deficit/Hyperactivity Disorder | journal = Journal of Attention Disorders | volume = 6 | pages = S109–S119 | year = 2002 | issue = Suppl 1 | pmid = 12685525 | doi = 10.1177/070674370200601s13 | s2cid = 26801069 }}</ref> It acts as an [[agonist]] at neural [[nicotinic acetylcholine receptor]]s, [[Nicotinic acetylcholine receptor#Subunits|subtype-selective]] binding with high [[Dissociation constant|affinity]] to the [[Α4β2 nicotinic receptor|α<sub>4</sub>β<sub>2</sub>]], [[Α7 nicotinic acetylcholine receptor|α<sub>7</sub>]]/[[5-HT3 receptor|5-HT<sub>3</sub>]], and α<sub>2</sub>β<sub>2</sub> [[nicotinic acetylcholine receptors]] but not [[ganglion type nicotinic receptor|α3β4]] receptors<ref name="pmid9031746">{{cite journal | vauthors = Papke RL, Thinschmidt JS, Moulton BA, Meyer EM, Poirier A | title = Activation and inhibition of rat neuronal nicotinic receptors by ABT-418 | journal = British Journal of Pharmacology | volume = 120 | issue = 3 | pages = 429–438 | date = February 1997 | pmid = 9031746 | pmc = 1564486 | doi = 10.1038/sj.bjp.0700930 }}</ref><ref>{{cite journal | vauthors = Dallanoce C, Magrone P, Matera C, Lo Presti L, De Amici M, Riganti L, Clementi F, Gotti C, De Micheli C | display-authors = 6 | title = Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes | journal = European Journal of Medicinal Chemistry | volume = 45 | issue = 12 | pages = 5594–5601 | date = December 2010 | pmid = 20932609 | doi = 10.1016/j.ejmech.2010.09.009 }}</ref><ref name="pmid7566493">{{cite journal | vauthors = Briggs CA, McKenna DG, Piattoni-Kaplan M | title = Human alpha 7 nicotinic acetylcholine receptor responses to novel ligands | journal = Neuropharmacology | volume = 34 | issue = 6 | pages = 583–590 | date = June 1995 | pmid = 7566493 | doi = 10.1016/0028-3908(95)00028-5 | s2cid = 54338489 }}</ref> ABT-418 was reasonably effective for both applications and fairly well tolerated, but produced some side effects, principally [[nausea]], and it is unclear whether ABT-418 itself will proceed to clinical development or if another similar drug will be used instead.<ref name="pmid17689498">{{cite journal | vauthors = Wilens TE, Decker MW | title = Neuronal nicotinic receptor agonists for the treatment of attention-deficit/hyperactivity disorder: focus on cognition | journal = Biochemical Pharmacology | volume = 74 | issue = 8 | pages = 1212–1223 | date = October 2007 | pmid = 17689498 | pmc = 2974320 | doi = 10.1016/j.bcp.2007.07.002 }}</ref>

== See also ==
* [[Epiboxidine]]
* [[Anabaseine]]
{{clear}}
== References ==
{{Reflist|2}}

{{Stimulants}}

{{Antidementia}}
{{Anxiolytics}}
{{Nicotinic acetylcholine receptor modulators}}

{{DEFAULTSORT:Abt-418}}
[[Category:Isoxazoles]]
[[Category:Nicotinic agonists]]
[[Category:Nootropics]]
[[Category:Pyrrolidines]]
[[Category:Stimulants]]

{{anxiolytic-stub}}