AFDX-384

{{Short description|Chemical compound}}

{{drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 462652478

| IUPAC_name = N-(2-[(2R)-2-[(dipropylamino)methyl]piperidin-1-yl]ethyl)-6-oxo-5H-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide

| image = AFDX-384.svg

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

| CAS_number = 118290-27-0

| ATC_prefix =

| ATC_suffix =

| ATC_supplemental =

| PubChem = 119357

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 73338

| C=27 | H=38 | N=6 | O=2

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

| ChemSpiderID = 26233613

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C27H38N6O2/c1-3-16-31(17-4-2)20-21-10-7-8-18-32(21)19-15-29-27(35)33-24-13-6-5-11-22(24)26(34)30-23-12-9-14-28-25(23)33/h5-6,9,11-14,21H,3-4,7-8,10,15-20H2,1-2H3,(H,29,35)(H,30,34)/t21-/m1/s1

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

| StdInChIKey = MZDYABXXPZNUCT-OAQYLSRUSA-N

| smiles = O=C1Nc2cccnc2N(c4c1cccc4)C(=O)NCCN3CCCCC3CN(CCC)CCC

| bioavailability =

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}}

AFDX-384 (BIBN-161) is a drug which acts as a selective antagonist of the muscarinic acetylcholine receptors, with selectivity for the M₂ and M₄ subtypes. It is used mainly for mapping the distribution of M₂ and M₄ muscarinic receptors in the brain, and studying their involvement in the development and treatment of dementia and schizophrenia.{{cite journal |vauthors=Tränkle C, Andresen I, Lambrecht G, Mohr K |title=M2 receptor binding of the selective antagonist AF-DX 384: possible involvement of the common allosteric site |journal=Molecular Pharmacology |volume=53 |issue=2 |pages=304–12 |date=February 1998 |pmid=9463489 |doi= 10.1124/mol.53.2.304}}{{cite journal |vauthors=Kitaichi K, Day JC, Quirion R |title=A novel muscarinic M(4) receptor antagonist provides further evidence of an autoreceptor role for the muscarinic M(2) receptor sub-type |journal=European Journal of Pharmacology |volume=383 |issue=1 |pages=53–6 |date=October 1999 |pmid=10556681 |doi= 10.1016/S0014-2999(99)00607-X}}{{cite journal |vauthors=Martin J, Deagostino A, Perrio C, Dauphin F, Ducandas C, Morin C, Desbène PL, Lasne MC |title=Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M2 receptors |journal=Bioorganic & Medicinal Chemistry |volume=8 |issue=3 |pages=591–600 |date=March 2000 |pmid=10732976 |doi= 10.1016/S0968-0896(99)00307-7}}{{cite journal |vauthors=Piggott M, Owens J, O'Brien J, Paling S, Wyper D, Fenwick J, Johnson M, Perry R, Perry E |title=Comparative distribution of binding of the muscarinic receptor ligands pirenzepine, AF-DX 384, (R,R)-I-QNB and (R,S)-I-QNB to human brain |journal=Journal of Chemical Neuroanatomy |volume=24 |issue=3 |pages=211–23 |date=September 2002 |pmid=12297267 |doi= 10.1016/S0891-0618(02)00066-2|s2cid=1935197 }}{{cite journal |vauthors=Zavitsanou K, Katsifis A, Yu Y, Huang XF |title=M2/M4 muscarinic receptor binding in the anterior cingulate cortex in schizophrenia and mood disorders |journal=Brain Research Bulletin |volume=65 |issue=5 |pages=397–403 |date=May 2005 |pmid=15833594 |doi=10.1016/j.brainresbull.2005.02.007 |s2cid=19527958 }}{{cite journal |vauthors=Teaktong T, Piggott MA, Mckeith IG, Perry RH, Ballard CG, Perry EK |title=Muscarinic M2 and M4 receptors in anterior cingulate cortex: relation to neuropsychiatric symptoms in dementia with Lewy bodies |journal=Behavioural Brain Research |volume=161 |issue=2 |pages=299–305 |date=June 2005 |pmid=15922057 |doi=10.1016/j.bbr.2005.02.019 |s2cid=34247659 }}{{cite journal |vauthors=Gibbons AS, Scarr E, McLean C, Sundram S, Dean B |title=Decreased muscarinic receptor binding in the frontal cortex of bipolar disorder and major depressive disorder subjects |journal=Journal of Affective Disorders |volume=116 |issue=3 |pages=184–91 |date=August 2009 |pmid=19103464 |pmc=2724602 |doi=10.1016/j.jad.2008.11.015 }}