An inhibitor of FLAP
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MK-0591

Item No. 37322

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-[(4-chlorophenyl)methyl]-3-[(1,1-dimethylethyl)thio]-α,α-dimethyl-5-(2-quinolinylmethoxy)-1H-indole-2-propanoic acid
CAS Number
136668-42-3
Synonyms
  • L-686,708
  • Quiflapon
Molecular Formula
C34H35ClN2O3S
Formula Weight
587.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 50 mg/ml
λmax
230 nm
SMILES
O=C(C(C)(CC1=C(C2=C(N1CC3=CC=C(C=C3)Cl)C=CC(OCC4=NC5=C(C=C4)C=CC=C5)=C2)SC(C)(C)C)C)O
InChi Code
InChI=1S/C34H35ClN2O3S/c1-33(2,3)41-31-27-18-26(40-21-25-15-12-23-8-6-7-9-28(23)36-25)16-17-29(27)37(20-22-10-13-24(35)14-11-22)30(31)19-34(4,5)32(38)39/h6-18H,19-21H2,1-5H3,(H,38,39)
InChi Key
NZOONKHCNQFYCI-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $74

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    5 mg

    $329

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    10 mg

    $548

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    25 mg

    $1,094

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    Product Description

    MK-0591 is an inhibitor of 5-lipoxygenase-activating protein (FLAP; IC50 = 1.6 nM for the human enzyme).1 It inhibits leukotriene B4 (LTB4; Item No. 20110) biosynthesis in isolated rat neutrophils stimulated with the calcium ionophore A23187 (Item No. 11016; IC50 = 6 nM) but does not inhibit 5-lipoxygenase (5-LO) in a cell-free assay (IC50 = > 4 µM for the rat enzyme). MK-0591 (0.3 and 1 mg/kg) prevents increases in airway resistance and decreases in dynamic compliance in Ascaris antigen-induced squirrel monkeys. It decreases proteinuria and reduces decreases in renal LTC4 synthase activity in a rat model of glomerulonephritis induced by nephrotoxic rabbit serum when administered at a dose of 60 mg/kg.2 MK-0591 (8 µM) also induces apoptosis in LNCaP prostate cancer cells.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Brideau, C., Chan, C., Charleson, S., et al. Pharmacology of MK-0591 (3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(quinolin-2-yl-methoxy)-indol-2-yl]-2,2-dimethyl propanoic acid), a potent, orally active leukotriene biosynthesis inhibitor. Can. J. Physiol. Pharmacol. 70(6), 799-807 (1992).

    2. Petric, R., and Ford-Hutchinson, A. Inhibition of leukotriene biosynthesis improves renal function in experimental glomerulonephritis. J. Lipid Mediat. Cell Signal 11(3), 231-240 (1995).

    3. Sarveswaran, S., Myers, C.E., and Ghosh, J. MK591, a leukotriene biosynthesis inhibitor, induces apoptosis in prostate cancer cells: Synergistic action with LY294002, an inhibitor of phosphatidylinositol 3'-kinase. Cancer Lett. 291(2), 167-176 (2010).