ABT-418

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477235109

| IUPAC_name = 3-Methyl-5-[(2S)-1-methylpyrrolidin-2-yl]-1,2-oxazole

| image = ABT-418.svg

| width = 175

| tradename =

| routes_of_administration =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 147402-53-7

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

| UNII = B9I6MZL7BW

| ATC_suffix = None

| PubChem = 119380

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

| ChemSpiderID = 106627

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 274525

| C=9 | H=14 | N=2 | O=1

| smiles = CC1=NOC(=C1)[C@@H]2CCCN2C

| 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

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

| StdInChIKey = ILLGYRJAYAAAEW-QMMMGPOBSA-N

}}

ABT-418 is a drug developed by Abbott, that has nootropic, neuroprotective and anxiolytic effects,{{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 }}{{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 }}{{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 }}{{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 }}{{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 }} and has been researched for treatment of both Alzheimer's disease{{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 }} and ADHD.{{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 }}{{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 }}{{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 }} It acts as an agonist at neural nicotinic acetylcholine receptors, subtype-selective binding with high affinity to the α₄β₂, α₇/5-HT₃, and α₂β₂ nicotinic acetylcholine receptors but not α3β4 receptors{{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 }}{{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 }}{{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 }} 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.{{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 }}