AM-679 (FLAP inhibitor)

AM-679 (FLAP inhibitor)

Systematic (IUPAC) name
3-(5-[(S)-1-acetyl-2,3-dihydro-1H-indol-2-ylmethoxy]-3-t-butylsulfanyl-1-[4-(5-methoxypyrimidin-2-yl)benzyl]-1H-indol-2-yl)-2,2-dimethylpropionic acid
Identifiers
CAS Number	1206880-66-1
PubChem	CID 44627267
ChemSpider	25991470
Chemical data
Formula	C40H44N4O5S
Molar mass	692.864 g/mol
SMILES n5cc(OC)cnc5-c6ccc(cc6)Cn(c1CC(C)(C)C(=O)O)c4ccc(cc4c1SC(C)(C)C)OCC3Cc2ccccc2N3C(=O)C
InChI InChI=1S/C39H42N4O5S/c1-24(44)43-28(18-27-10-8-9-11-32(27)43)23-48-29-16-17-33-31(19-29)34(49-38(2,3)4)35(39(5,6)37(45)46)42(33)22-25-12-14-26(15-13-25)36-40-20-30(47-7)21-41-36/h8-17,19-21,28H,18,22-23H2,1-7H3,(H,45,46)/t28-/m0/s1 Key:XTSOSRWDZSKOSB-NDEPHWFRSA-N
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AM-679 is a drug which acts as a selective inhibitor of 5-Lipoxygenase-activating protein (FLAP). This protein is involved in the production of cysteinyl leukotrienes which are involved in inflammation, and AM-679 has anti-inflammatory effects in animal studies.^[1][2]

References

1. Stock N, Baccei C, Bain G, Broadhead A, Chapman C, Darlington J, King C, Lee C, Li Y, Lorrain DS, Prodanovich P, Rong H, Santini A, Zunic J, Evans JF, Hutchinson JH, Prasit P (January 2010). "5-Lipoxygenase-activating protein inhibitors. Part 2: 3-{5-((S)-1-Acetyl-2,3-dihydro-1H-indol-2-ylmethoxy)-3-tert-butylsulfanyl-1-[4-(5-methoxy-pyrimidin-2-yl)-benzyl]-1H-indol-2-yl}-2,2-dimethyl-propionic acid (AM679)--a potent FLAP inhibitor". Bioorganic & Medicinal Chemistry Letters 20 (1): 213–7. doi:10.1016/j.bmcl.2009.10.131. PMID 19914828.
2. Musiyenko, A.; Correa, L.; Stock, N.; Hutchinson, J. H.; Lorrain, D. S.; Bain, G.; Evans, J. F.; Barik, S. (2009). "A Novel 5-Lipoxygenase-Activating Protein Inhibitor, AM679, Reduces Inflammation in the Respiratory Syncytial Virus-Infected Mouse Eye". Clinical and Vaccine Immunology 16 (11): 1654–9. doi:10.1128/CVI.00220-09. PMC 2772391. PMID 19759251.