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ABT-418

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Chemical compound

Pharmaceutical compound

ABT-418
Identifiers

IUPAC name 3-Methyl-5-[(2S)-1-methylpyrrolidin-2-yl]-1,2-oxazole
CAS Number	147402-53-7^N
PubChemCID	119380
ChemSpider	106627^Y
UNII	B9I6MZL7BW
ChEMBL	ChEMBL274525^Y
CompTox Dashboard(EPA)	DTXSID10163711
Chemical and physical data
Formula	C₉H₁₄N₂O
Molar mass	166.224 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=NOC(=C1)[C@@H]2CCCN2C
InChI InChI=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^Y Key:ILLGYRJAYAAAEW-QMMMGPOBSA-N^Y
^NY (what is this?) (verify)

ABT-418 is a drug developed byAbbott, that hasnootropic,neuroprotective andanxiolytic effects,^[1]^[2]^[3]^[4]^[5] and has been researched for treatment of bothAlzheimer's disease^[6] andADHD.^[7]^[8]^[9] It acts as anagonist at neuralnicotinic acetylcholine receptors,subtype-selective binding with highaffinity to theα₄β₂,α₇/5-HT₃, and α₂β₂nicotinic acetylcholine receptors but notα3β4 receptors^[10]^[11]^[12] ABT-418 was reasonably effective for both applications and fairly well tolerated, but produced some side effects, principallynausea, and it is unclear whether ABT-418 itself will proceed to clinical development or if another similar drug will be used instead.^[13]

References

[edit]

^Arneric SP, Sullivan JP, Briggs CA, Donnelly-Roberts D, Anderson DJ, Raszkiewicz JL, et al. (July 1994)."(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".The Journal of Pharmacology and Experimental Therapeutics.270 (1):310–318.PMID 7518514. Archived fromthe original on 2005-05-07. Retrieved2008-06-08.
^Decker MW, Brioni JD, Sullivan JP, Buckley MJ, Radek RJ, Raszkiewicz JL, et al. (July 1994)."(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".The Journal of Pharmacology and Experimental Therapeutics.270 (1):319–328.PMID 7913497. Archived fromthe original on 2005-05-07. Retrieved2008-06-08.
^Brioni JD, O'Neill AB, Kim DJ, Buckley MJ, Decker MW, Arneric SP (October 1994)."Anxiolytic-like effects of the novel cholinergic channel activator ABT-418".The Journal of Pharmacology and Experimental Therapeutics.271 (1):353–361.PMID 7965735. Archived fromthe original on 2009-09-05. Retrieved2008-06-08.
^Prendergast MA, Terry AV, Jackson WJ, Marsh KC, Decker MW, Arneric SP, Buccafusco JJ (April 1997). "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".Psychopharmacology.130 (3):276–284.doi:10.1007/s002130050240.PMID 9151363.S2CID 34377165.
^Dallanoce C, Magrone P, Matera C, Lo Presti L, De Amici M, Riganti L, et al. (December 2010). "Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes".European Journal of Medicinal Chemistry.45 (12):5594–5601.doi:10.1016/j.ejmech.2010.09.009.PMID 20932609.
^Potter A, Corwin J, Lang J, Piasecki M, Lenox R, Newhouse PA (March 1999). "Acute effects of the selective cholinergic channel activator (nicotinic agonist) ABT-418 in Alzheimer's disease".Psychopharmacology.142 (4):334–342.doi:10.1007/s002130050897.PMID 10229057.S2CID 27337634.
^Wilens TE, Biederman J, Spencer TJ, Bostic J, Prince J, Monuteaux MC, et al. (December 1999). "A pilot controlled clinical trial of ABT-418, a cholinergic agonist, in the treatment of adults with attention deficit hyperactivity disorder".The American Journal of Psychiatry.156 (12):1931–1937.doi:10.1176/ajp.156.12.1931.PMID 10588407.S2CID 20375475.
^Horrigan JP (April 2001). "Present and future pharmacotherapeutic options for adult attention deficit/hyperactivity disorder".Expert Opinion on Pharmacotherapy.2 (4):573–586.doi:10.1517/14656566.2.4.573.PMID 11336608.S2CID 41914443.
^Spencer T, Biederman J (2002). "Non-stimulant treatment for Attention-Deficit/Hyperactivity Disorder".Journal of Attention Disorders.6 (Suppl 1):S109–S119.doi:10.1177/070674370200601s13.PMID 12685525.S2CID 26801069.
^Papke RL, Thinschmidt JS, Moulton BA, Meyer EM, Poirier A (February 1997)."Activation and inhibition of rat neuronal nicotinic receptors by ABT-418".British Journal of Pharmacology.120 (3):429–438.doi:10.1038/sj.bjp.0700930.PMC 1564486.PMID 9031746.
^Dallanoce C, Magrone P, Matera C, Lo Presti L, De Amici M, Riganti L, et al. (December 2010). "Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes".European Journal of Medicinal Chemistry.45 (12):5594–5601.doi:10.1016/j.ejmech.2010.09.009.PMID 20932609.
^Briggs CA, McKenna DG, Piattoni-Kaplan M (June 1995). "Human alpha 7 nicotinic acetylcholine receptor responses to novel ligands".Neuropharmacology.34 (6):583–590.doi:10.1016/0028-3908(95)00028-5.PMID 7566493.S2CID 54338489.
^Wilens TE, Decker MW (October 2007)."Neuronal nicotinic receptor agonists for the treatment of attention-deficit/hyperactivity disorder: focus on cognition".Biochemical Pharmacology.74 (8):1212–1223.doi:10.1016/j.bcp.2007.07.002.PMC 2974320.PMID 17689498.

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ATC code:N06B

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Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine (tobacco) Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III