AM-679 (FLAP inhibitor)

This article is about the FLAP inhibitor. For the cannabinoid agonist, see AM-679 (cannabinoid).

AM-679 (FLAP inhibitor)
Identifiers

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
CAS Number	1206880-66-1
PubChem (CID)	44627267
ChemSpider	25991470^Y
Chemical and physical data
Formula	C₄₀H₄₄N₄O₅S
Molar mass	692.864 g/mol
3D model (Jmol)	Interactive image
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^Y Key:XTSOSRWDZSKOSB-NDEPHWFRSA-N^Y
(verify)

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

↑ 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.
↑ 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.

BLT₁	Agonists: 12-HETE 20-Hydroxy-LTB₄ Leukotriene B₄ LY-255283 Antagonists: 20-Carboxy-LTB₄ Amelubant CGS-23131 (LY-223982) CGS-25019C CP-105696 CP-195543 Etalocib LY-293111 Moxilubant ONO-4057 RG-14893 RP-69698 SB-209247 SC-53228 Ticolubant U-75302 ZK-158252

BLT₂	Agonists: 12-HETE 12-HHT 12-HpETE 15-HETE 15-HpETE 20-Hydroxy-LTB₄ Leukotriene B₄ Antagonists: CP-195543 LY-255283 ZK-158252

CysLT₁	Agonists: Leukotriene C₄ Leukotriene D₄ Leukotriene E₄ Antagonists: Ablukast BAYu9773 BAYu9916 BAYx7195 Cinalukast FPL-55712 ICI-198615 Iralukast LY-170680 Masilukast MK-571 Montelukast ONO-1078 Pobilukast Pranlukast Ritolukast SKF-104353 SR-2640 Sulukast Tipelukast Tomelukast Verlukast Zafirlukast ZD-3523

CysLT₂	Agonists: Leukotriene C₄ Leukotriene D₄ Leukotriene E₄ Antagonists: BAYu9773 BAYu9916

CysLT_E	Agonists: Leukotriene E₄

5-Lipoxygenase	2-TEDC Baicalein BW-A4C BW-B70C Caffeic acid CDC CJ-13610 Curcumin Fenleuton Hyperforin Hypericum perforatum (St. John's Wort) Meclofenamic acid (meclofenamate) Minocycline N-Stearoyldopamine Timegadine Zileuton FLAP inhibitors: AM-103 AM-679 BAYx1005 MK-591 MK-886

12-Lipoxygenase	2-TEDC 3-Methoxytropolone Baicalein CDC

15-Lipoxygenase	2-TEDC CDC Luteolin PD-146176

LTA₄ hydrolase	Acebilustat Captopril DG-051 Fosinoprilat JNJ-26993135 SA-6541 SC-57461A Ubenimex (bestatin)

LTB₄ ω-hydroxylase	17-Octadecynoic acid

LTC₄ synthase	Azelastine MK-886

LTC₄ hydrolase	Acivicin Serine-borate complex

LTD₄ hydrolase	Cilastatin Ubenimex (bestatin)

Others

See also: Prostanoids

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