AFDX-384 Knowpia

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	118290-27-0 ;
PubChem CID	119357;
ChemSpider	26233613 ;
ChEBI	CHEBI:73338 ;
CompTox Dashboard (EPA)	DTXSID60922653 ;
Chemical and physical data
Formula	C27H38N6O2
Molar mass	478.641 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:MZDYABXXPZNUCT-OAQYLSRUSA-N ;
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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.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

References edit

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

[pmid9463489-1] 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.

[pmid10556681-2] 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.

[pmid10732976-3] 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.

[pmid12297267-4] 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.

[pmid15833594-5] 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.

[pmid15922057-6] 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.

[pmid19103464-7] 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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Summary

See also edit

References edit

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	118290-27-0^Y
PubChem CID	119357
ChemSpider	26233613^Y
ChEBI	CHEBI:73338^N
CompTox Dashboard (EPA)	DTXSID60922653
Chemical and physical data
Formula	C₂₇H₃₈N₆O₂
Molar mass	478.641 g·mol⁻¹
3D model (JSmol)	Interactive image
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
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