An inhibitor of MAGL, FAAH, cPLA2, and iPLA2
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Methyl Arachidonyl Fluorophosphonate

Item No. 70660

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5Z,8Z,11Z,14Z-eicosatetraenyl-phosphonofluoridic acid, methyl ester
CAS Number
188404-10-6
Synonyms
  • MAFP
Molecular Formula
C21H36FO2P
Formula Weight
370.5
Purity
≥98%
Formulation
A 10 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: 3 mg/mlDMSO: 3 mg/mlEthanol: 3.5 mg/mlEthanol:PBS (pH 7.2) 1:1: .5 mg/mlPBS (7.2): <1 mg/ml (colloidal suspension
SMILES
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCCP(F)(OC)=O
InChi Code
InChI=1S/C21H36FO2P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3/b8-7-,11-10-,14-13-,17-16-
InChi Key
KWKZCGMJGHHOKJ-ZKWNWVNESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    5 mg

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    10 mg

    $242

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    25 mg

    $512

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    Product Description

    Methyl arachidonyl fluorophosphonate (MAFP) is an inhibitor of monoacylglycerol lipase (MAGL) and fatty acid amide hydrolase (FAAH; IC50s = 26 and 0.33 nM, respectively).1 It is also an irreversible inhibitor of cytosolic phospholipase A2 (cPLA2), as well as calcium-independent PLA2 (iPLA2; IC50 = 500 nM).2,3,4 MAFP inhibits A23187-induced arachidonic acid release from human platelets with an IC50 value of 600 nM.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Matuszak, N., Muccioli, G.G., Labar, G., et al. Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors. J. Med. Chem. 52(23), 7410-7420 (2009).

    2. Huang, Z., Liu, S., Street, I., et al. Methyl arachidonyl fluorophosphonate, a potent irreversible cPLA2 inhibitor, blocks the mobilization of arachidonic acid in human platelets and neutrophils. Mediators Inflamm. 3, 307-308 (1994).

    3. Lio, Y.C., Reynolds, L.J., Balsinde, J., et al. Irreversible inhibition of Ca2+-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim. Biophys. Acta 1302(1), 55-60 (1996).

    4. Balsinde, J., and Dennis, E.A. Distinct roles in signal transduction for each of the phospholipase A2 enzymes present in P388D1 macrophages. The Journal of Biological Chemisty 271(12), 6758-6765 (1996).

    Product Citations

    Futatsugi, K., Cabral, S., Kung, D.W., et al. Discovery of ervogastat (PF-06865571): A potent and selective inhibitor of diacylglycerol acyltransferase 2 for the treatment of non-alcoholic steatohepatitis. J. Med. Chem. 65(22), 15000-15013 (2022).

    Wyatt, R.M., Fraser, I., Welty, N., et al. Pharmacologic characterization of JNJ-42226314, [1-(4-fluorophenyl)indol-5-yl]-[3-[4-(thiazole-2-carbonyl)piperazin-1-yl]azetidin-1-yl]methanone, a reversible, selective, and potent monoacylglycerol lipase inhibitor. J. Pharmacol. Exp. Ther. 372(3), 339-353 (2020).

    Archambault, A.-S., Turcotte, C., Martin, C., et al. Comparison of eight 15-lipoxygenase (LO) inhibitors on the biosynthesis of 15-LO metabolites by human neutrophils and eosinophils. PLoS One 13(8), e0202424 (2018).

    Simon, G.M., and Cravatt, B.F. Endocannabinoid biosynthesis proceeding through glycerophospho-N-acyl ethanolamine and a role for α/β-hydrolase 4 in this pathway. The Journal of Biological Chemisty 281(36), 26465-26472 (2006).

    Goparaju, S.K., Ueda, N., Yamaguchi, H., et al. Anandamide amidohydrolase reacting with 2-arachidonoylglycerol, another cannabinoid receptor ligand. FEBS Lett. 422, 69-73 (1998).