AFDX-384

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.[1][2][3][4][5][6][7]

AFDX-384
Identifiers
IUPAC name
  • N-(2-[(2R)-2-[(dipropylamino)methyl]piperidin-1-yl]ethyl)-6-oxo-5H-pyrido[2,3-b][1,4]benzodiazepine-11-carboxamide
CAS Number
PubChem CID
ChemSpider
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H38N6O2
Molar mass478.641 g·mol−1
3D model (JSmol)
SMILES
  • O=C1Nc2cccnc2N(c4c1cccc4)C(=O)NCCN3CCCCC3CN(CCC)CCC
InChI
  • InChI=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 Y
  • Key:MZDYABXXPZNUCT-OAQYLSRUSA-N Y
 NY (what is this?)  (verify)

See also

References
  1. Tränkle C, Andresen I, Lambrecht G, Mohr K (February 1998). "M2 receptor binding of the selective antagonist AF-DX 384: possible involvement of the common allosteric site". Molecular Pharmacology. 53 (2): 304–12. doi:10.1124/mol.53.2.304. PMID 9463489.
  2. Kitaichi K, Day JC, Quirion R (October 1999). "A novel muscarinic M(4) receptor antagonist provides further evidence of an autoreceptor role for the muscarinic M(2) receptor sub-type". European Journal of Pharmacology. 383 (1): 53–6. doi:10.1016/S0014-2999(99)00607-X. PMID 10556681.
  3. Martin J, Deagostino A, Perrio C, Dauphin F, Ducandas C, Morin C, Desbène PL, Lasne MC (March 2000). "Syntheses of R and S isomers of AF-DX 384, a selective antagonist of muscarinic M2 receptors". Bioorganic & Medicinal Chemistry. 8 (3): 591–600. doi:10.1016/S0968-0896(99)00307-7. PMID 10732976.
  4. Piggott M, Owens J, O'Brien J, Paling S, Wyper D, Fenwick J, Johnson M, Perry R, Perry E (September 2002). "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 of Chemical Neuroanatomy. 24 (3): 211–23. doi:10.1016/S0891-0618(02)00066-2. PMID 12297267. S2CID 1935197.
  5. Zavitsanou K, Katsifis A, Yu Y, Huang XF (May 2005). "M2/M4 muscarinic receptor binding in the anterior cingulate cortex in schizophrenia and mood disorders". Brain Research Bulletin. 65 (5): 397–403. doi:10.1016/j.brainresbull.2005.02.007. PMID 15833594. S2CID 19527958.
  6. Teaktong T, Piggott MA, Mckeith IG, Perry RH, Ballard CG, Perry EK (June 2005). "Muscarinic M2 and M4 receptors in anterior cingulate cortex: relation to neuropsychiatric symptoms in dementia with Lewy bodies". Behavioural Brain Research. 161 (2): 299–305. doi:10.1016/j.bbr.2005.02.019. PMID 15922057. S2CID 34247659.
  7. Gibbons AS, Scarr E, McLean C, Sundram S, Dean B (August 2009). "Decreased muscarinic receptor binding in the frontal cortex of bipolar disorder and major depressive disorder subjects". Journal of Affective Disorders. 116 (3): 184–91. doi:10.1016/j.jad.2008.11.015. PMC 2724602. PMID 19103464.
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