MK-886
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MedKoo CAT#: 407217

CAS#: 118414-82-7 (free acid)

Description: MK-886, also known as L 663536, is a leukotriene antagonist. It may perform this by blocking the 5-lipoxygenase activating protein (FLAP), thus inhibiting 5-lipoxygenase (5-LOX), and may help in treating atherosclerosis. MK-886 inhibits cyclooxygenase-1 activity and suppresses platelet aggregation. MK-886 induces changes in cell cycle and increases apoptosis after photodynamic therapy with hypericin. MK-886 enhances tumour necrosis factor-alpha-induced differentiation and apoptosis.


Price and Availability

Size Price Shipping out time Quantity
10mg USD 115 Same day
25mg USD 250 Same day
50mg USD 450 Same day
100mg USD 650 Same day
200mg USD 950 Same day
500mg USD 1650 Same day
1g USD 2750 Same day
2g USD 4650 Same day
Inquire bulk and customized quantity

Pricing updated 2020-10-23. Prices are subject to change without notice.

MK-886 (L-663,536), purity > 98%, is in stock. The same day shipping after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 407217
Name: MK-886
CAS#: 118414-82-7 (free acid)
Chemical Formula: C27H34ClNO2S
Exact Mass: 471.19988
Molecular Weight: 472.084
Elemental Analysis: C, 68.69; H, 7.26; Cl, 7.51; N, 2.97; O, 6.78; S, 6.79


Related CAS #: 118414-82-7 (free acid)   118427-55-7 (sodium)   1049737-88-3 (sodium hydrate)    

Synonym: MK-886; MK886; MK 886; L-663,536; L663,536; L 663,536; L-663536; L663536; L 663536.

IUPAC/Chemical Name: 3-[3-butylsulfanyl-1-[(4-chlorophenyl)methyl]-5-propan-2-yl-indol-2-yl]-2,2 -dimethyl-propanoic acid

InChi Key: VFMGWQLOCZBFCK-UHFFFAOYSA-N

InChi Code: InChI=1S/C27H34ClNO2S/c1-6-7-14-32-25-22-15-20(18(2)3)10-13-23(22)29(17-19-8-11-21(28)12-9-19)24(25)16-27(4,5)26(30)31/h8-13,15,18H,6-7,14,16-17H2,1-5H3,(H,30,31)

SMILES Code: O=C(O)C(C)(C)CC(N1CC2=CC=C(Cl)C=C2)=C(SCCCC)C3=C1C=CC(C(C)C)=C3


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (SDS):

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Kuchárová B, Mikeš J, Jendželovský R, Vargová J, Mikešová L, Jendželovská Z, Kovaľ J, Fedoročko P. Potentiation of hypericin-mediated photodynamic therapy cytotoxicity by MK-886: Focus on ABC transporters, GDF-15 and redox status. Photodiagnosis Photodyn Ther. 2015 Sep;12(3):490-503. doi: 10.1016/j.pdpdt.2015.04.008. Epub 2015 May 21. PubMed PMID: 26003114.

2: Huang JK, Huang CC, Lu T, Chang HT, Lin KL, Tsai JY, Liao WC, Chien JM, Jan CR. Effect of MK-886 on Ca2+ level and viability in PC3 human prostate cancer cells. Basic Clin Pharmacol Toxicol. 2009 Jun;104(6):441-7. doi: 10.1111/j.1742-7843.2009.00413.x. Epub 2009 Apr 3. PubMed PMID: 19371256.

3: Koeberle A, Siemoneit U, Northoff H, Hofmann B, Schneider G, Werz O. MK-886, an inhibitor of the 5-lipoxygenase-activating protein, inhibits cyclooxygenase-1 activity and suppresses platelet aggregation. Eur J Pharmacol. 2009 Apr 17;608(1-3):84-90. doi: 10.1016/j.ejphar.2009.02.023. Epub 2009 Feb 23. PubMed PMID: 19239910.

4: Kleban J, Mikes J, Horváth V, Sacková V, Hofmanová J, Kozubík A, Fedorocko P. Mechanisms involved in the cell cycle and apoptosis of HT-29 cells pre-treated with MK-886 prior to photodynamic therapy with hypericin. J Photochem Photobiol B. 2008 Nov 13;93(2):108-18. doi: 10.1016/j.jphotobiol.2008.07.007. Epub 2008 Aug 6. PubMed PMID: 18771933.

5: Daglar G, Karaca T, Yuksek YN, Gozalan U, Akbiyik F, Sokmensuer C, Gurel B, Kama NA. Effect of montelukast and MK-886 on hepatic ischemia-reperfusion injury in rats. J Surg Res. 2009 May 1;153(1):31-8. doi: 10.1016/j.jss.2008.02.052. Epub 2008 Mar 26. PubMed PMID: 18656901.

6: Uz T, Dimitrijevic N, Imbesi M, Manev H, Manev R. Effects of MK-886, a 5-lipoxygenase activating protein (FLAP) inhibitor, and 5-lipoxygenase deficiency on the forced swimming behavior of mice. Neurosci Lett. 2008 May 9;436(2):269-72. doi: 10.1016/j.neulet.2008.03.041. Epub 2008 Mar 21. PubMed PMID: 18403121; PubMed Central PMCID: PMC2423274.

7: Biserni A, Giannessi F, Sciarroni AF, Milazzo FM, Maggi A, Ciana P. In vivo imaging reveals selective peroxisome proliferator activated receptor modulator activity of the synthetic ligand 3-(1-(4-chlorobenzyl)-3-t-butylthio-5-isopropylindol-2-yl)-2,2-dimethylpropanoic acid (MK-886). Mol Pharmacol. 2008 May;73(5):1434-43. doi: 10.1124/mol.107.042689. Epub 2008 Feb 21. PubMed PMID: 18292206.

8: Imbesi M, Zavoreo I, Uz T, Sharma RP, Dimitrijevic N, Manev H, Manev R. 5-Lipoxygenase inhibitor MK-886 increases GluR1 phosphorylation in neuronal cultures in vitro and in the mouse cortex in vivo. Brain Res. 2007 May 25;1147:148-53. Epub 2007 Feb 14. PubMed PMID: 17349982.

9: Kleban J, Szilárdiová B, Mikes J, Horváth V, Sacková V, Brezáni P, Hofmanová J, Kozubík A, Fedorocko P. Pre-treatment of HT-29 cells with 5-LOX inhibitor (MK-886) induces changes in cell cycle and increases apoptosis after photodynamic therapy with hypericin. J Photochem Photobiol B. 2006 Aug 1;84(2):79-88. Epub 2006 Mar 20. PubMed PMID: 16545574.

10: Jawien J, Gajda M, Rudling M, Mateuszuk L, Olszanecki R, Guzik TJ, Cichocki T, Chlopicki S, Korbut R. Inhibition of five lipoxygenase activating protein (FLAP) by MK-886 decreases atherosclerosis in apoE/LDLR-double knockout mice. Eur J Clin Invest. 2006 Mar;36(3):141-6. PubMed PMID: 16506957.

11: Stika J, Vondrácek J, Hofmanová J, Simek V, Kozubík A. MK-886 enhances tumour necrosis factor-alpha-induced differentiation and apoptosis. Cancer Lett. 2006 Jun 18;237(2):263-71. Epub 2005 Jul 21. PubMed PMID: 16039040.

12: Riendeau D, Aspiotis R, Ethier D, Gareau Y, Grimm EL, Guay J, Guiral S, Juteau H, Mancini JA, Méthot N, Rubin J, Friesen RW. Inhibitors of the inducible microsomal prostaglandin E2 synthase (mPGES-1) derived from MK-886. Bioorg Med Chem Lett. 2005 Jul 15;15(14):3352-5. PubMed PMID: 15953724.

13: Anderson KM, Rubenstein M, Alrefai WA, Dudeja P, Tsui P, Guinan P, Harris JE. Reactive oxygen species and redox-induced programmed cell death due to MK 886: cells ("soil") "trump" agent ("seed"). In Vivo. 2005 Jan-Feb;19(1):109-18. PubMed PMID: 15796162.

14: Anderson KM, Rubenstein M, Tsui P, Harris JE. Disparate forms of MK 886-induced programmed death in BCL-2 (+) blood and BCL-2 (-) solid cancer cells and a putative "nuclear" Ca2+ channel: "soil" trumps "seed"? Med Hypotheses. 2005;64(2):307-11. PubMed PMID: 15607561.

15: Anderson KM, Rubenstein M, Alrefai WA, Dudeja P, Tsui P, Harris JE. Acute changes in U937 nuclear Ca2+ preceding type 1 "apoptotic" programmed cell death due to MK 886. Anticancer Res. 2004 Sep-Oct;24(5A):2601-15. PubMed PMID: 15517864.

16: Fan XM, Tu SP, Lam SK, Wang WP, Wu J, Wong WM, Yuen MF, Lin MC, Kung HF, Wong BC. Five-lipoxygenase-activating protein inhibitor MK-886 induces apoptosis in gastric cancer through upregulation of p27kip1 and bax. J Gastroenterol Hepatol. 2004 Jan;19(1):31-7. PubMed PMID: 14675240.

17: Anderson KM, Alrefai W, Bonomi P, Seed TM, Dudeja P, Hu Y, Harris JE. Caspase-dependent and -independent panc-1 cell death due to actinomycin D and MK 886 are additive but increase clonogenic survival. Exp Biol Med (Maywood). 2003 Sep;228(8):915-25. PubMed PMID: 12968063.

18: Stanke-Labesque F, Hardy G, Caron F, Cracowski JL, Bessard G. Inhibition of leukotriene synthesis with MK-886 prevents a rise in blood pressure and reduces noradrenaline-evoked contraction in L-NAME-treated rats. Br J Pharmacol. 2003 Sep;140(1):186-94. Epub 2003 Jul 29. PubMed PMID: 12967948; PubMed Central PMCID: PMC1574003.

19: Anderson KM, Alrefai W, Anderson C, Bonomi P, Harris J. MK 886 functions as a radiomimetic agent: genomic responses related to oxidative stress, the cell cycle, proliferation and programmed cell death in Panc-1 cells. Adv Exp Med Biol. 2002;507:451-6. PubMed PMID: 12664625.

20: Anderson KM, Alrefai WA, Dudeja PK, Jadko S, Bonomi P, Hu Y, Ou D, Harris JE. Increased cytosol Ca(2+) and type 1 programmed cell death in Bcl-2-positive U937 but not in Bcl-2-negative PC-3 and Panc-1 cells induced by the 5-lipoxygenase inhibitor MK 886. Prostaglandins Leukot Essent Fatty Acids. 2002 Apr;66(4):443-52. PubMed PMID: 12054916.