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MedKoo Cat#: 522669 | Name: MK-571 sodium
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

MK-571 is a selective, orally active CysLT1 receptor antagonist. It blocks the binding of LTD4, but not LTC4, to human and guinea pig lung membranes with Ki values of 0.22 nM and 2.1 nM, respectively. MK-571 attenuates kidney ischemia and reperfusion-induced airway hypersensitivity in rats. MK-571 alters bronchoalveolar lavage fluid proteome in a mouse asthma model.

Chemical Structure

MK-571 sodium
MK-571 sodium
CAS#115103-85-0 (sodium)

Theoretical Analysis

MedKoo Cat#: 522669

Name: MK-571 sodium

CAS#: 115103-85-0 (sodium)

Chemical Formula: C26H26ClN2NaO3S2

Exact Mass: 0.0000

Molecular Weight: 537.06

Elemental Analysis: C, 58.15; H, 4.88; Cl, 6.60; N, 5.22; Na, 4.28; O, 8.94; S, 11.94

Price and Availability

Size Price Availability Quantity
25mg USD 220.00 2 Weeks
50mg USD 400.00 2 Weeks
100mg USD 650.00 2 Weeks
200mg USD 1,050.00 2 Weeks
500mg USD 2,150.00 2 Weeks
1g USD 3,250.00 2 Weeks
2g USD 5,650.00 2 Weeks
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Related CAS #
115103-85-0 (sodium) 115104-28-4 (free acid)
Synonym
MK-571; MK 571; MK571; MK-571 sodium salt; L-660,711; L660,711; L 660,711; L-660711; L660711; L 660711.
IUPAC/Chemical Name
sodium (E)-3-(((3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)((3-(dimethylamino)-3-oxopropyl)thio)methyl)thio)propanoate
InChi Key
XNAYQOBPAXEYLI-AAGWESIMSA-M
InChi Code
InChI=1S/C26H27ClN2O3S2.Na/c1-29(2)24(30)12-14-33-26(34-15-13-25(31)32)20-5-3-4-18(16-20)6-10-22-11-8-19-7-9-21(27)17-23(19)28-22;/h3-11,16-17,26H,12-15H2,1-2H3,(H,31,32);/q;+1/p-1/b10-6+;
SMILES Code
O=C([O-])CCSC(C1=CC=CC(/C=C/C2=NC3=CC(Cl)=CC=C3C=C2)=C1)SCCC(N(C)C)=O.[Na+]
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
MK-571 (L-660711) sodium is an orally active, potent and selective competitive leukotriene D4 (LTD4) receptor antagonist, with Ki values of 0.22 and 2.1 nM in guinea pig and human lung membranes.
In vitro activity:
Constitutive and antigen-stimulated S1P release was inhibited by MK571, an inhibitor of ABCC1 (MRP1), but not by inhibitors of ABCB1 (MDR-1, P-glycoprotein). Reference: Proc Natl Acad Sci U S A. 2006 Oct 31;103(44):16394-9. https://pubmed.ncbi.nlm.nih.gov/17050692/
In vivo activity:
Consistent with a pathogenic role for MRP4 in PAH, WT mice exposed to hypoxia for 3 weeks showed reversal of hypoxic pulmonary hypertension (PH) following oral administration of the MRP4 inhibitor MK571, and Mrp4-/- mice were protected from hypoxic PH. Reference: J Clin Invest. 2011 Jul;121(7):2888-97. https://pubmed.ncbi.nlm.nih.gov/21670499/
Solvent mg/mL mM comments
Solubility
DMF 10.0 18.62
DMSO 30.0 55.86
Ethanol 1.0 1.86
PBS (pH 7.2) 10.0 18.62
Water 26.7 49.65
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 537.06 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Ruiz I, Nevers Q, Hernández E, Ahnou N, Brillet R, Softic L, Donati F, Berry F, Hamadat S, Fourati S, Pawlotsky JM, Ahmed-Belkacem A. MK-571, a Cysteinyl Leukotriene Receptor 1 Antagonist, Inhibits Hepatitis C Virus Replication. Antimicrob Agents Chemother. 2020 May 21;64(6):e02078-19. doi: 10.1128/AAC.02078-19. PMID: 32179525; PMCID: PMC7269486. 2. Mitra P, Oskeritzian CA, Payne SG, Beaven MA, Milstien S, Spiegel S. Role of ABCC1 in export of sphingosine-1-phosphate from mast cells. Proc Natl Acad Sci U S A. 2006 Oct 31;103(44):16394-9. doi: 10.1073/pnas.0603734103. Epub 2006 Oct 18. PMID: 17050692; PMCID: PMC1637593. 3. Hara Y, Sassi Y, Guibert C, Gambaryan N, Dorfmüller P, Eddahibi S, Lompré AM, Humbert M, Hulot JS. Inhibition of MRP4 prevents and reverses pulmonary hypertension in mice. J Clin Invest. 2011 Jul;121(7):2888-97. doi: 10.1172/JCI45023. Epub 2011 Jun 13. PMID: 21670499; PMCID: PMC3223830. 4. Jones TR, Zamboni R, Belley M, Champion E, Charette L, Ford-Hutchinson AW, Frenette R, Gauthier JY, Leger S, Masson P, et al. Pharmacology of L-660,711 (MK-571): a novel potent and selective leukotriene D4 receptor antagonist. Can J Physiol Pharmacol. 1989 Jan;67(1):17-28. doi: 10.1139/y89-004. PMID: 2540892.
In vitro protocol:
1. Ruiz I, Nevers Q, Hernández E, Ahnou N, Brillet R, Softic L, Donati F, Berry F, Hamadat S, Fourati S, Pawlotsky JM, Ahmed-Belkacem A. MK-571, a Cysteinyl Leukotriene Receptor 1 Antagonist, Inhibits Hepatitis C Virus Replication. Antimicrob Agents Chemother. 2020 May 21;64(6):e02078-19. doi: 10.1128/AAC.02078-19. PMID: 32179525; PMCID: PMC7269486. 2. Mitra P, Oskeritzian CA, Payne SG, Beaven MA, Milstien S, Spiegel S. Role of ABCC1 in export of sphingosine-1-phosphate from mast cells. Proc Natl Acad Sci U S A. 2006 Oct 31;103(44):16394-9. doi: 10.1073/pnas.0603734103. Epub 2006 Oct 18. PMID: 17050692; PMCID: PMC1637593.
In vivo protocol:
1. Hara Y, Sassi Y, Guibert C, Gambaryan N, Dorfmüller P, Eddahibi S, Lompré AM, Humbert M, Hulot JS. Inhibition of MRP4 prevents and reverses pulmonary hypertension in mice. J Clin Invest. 2011 Jul;121(7):2888-97. doi: 10.1172/JCI45023. Epub 2011 Jun 13. PMID: 21670499; PMCID: PMC3223830. 2. Jones TR, Zamboni R, Belley M, Champion E, Charette L, Ford-Hutchinson AW, Frenette R, Gauthier JY, Leger S, Masson P, et al. Pharmacology of L-660,711 (MK-571): a novel potent and selective leukotriene D4 receptor antagonist. Can J Physiol Pharmacol. 1989 Jan;67(1):17-28. doi: 10.1139/y89-004. PMID: 2540892.
1: Yeh DY, Yang YC, Wang JJ. Hepatic Warm Ischemia-Reperfusion-Induced Increase in Pulmonary Capillary Filtration Is Ameliorated by Administration of a Multidrug Resistance-Associated Protein 1 Inhibitor and Leukotriene D4 Antagonist (MK-571) Through Reducing Neutrophil Infiltration and Pulmonary Inflammation and Oxidative Stress in Rats. Transplant Proc. 2015 May;47(4):1087-91. doi: 10.1016/j.transproceed.2014.10.061. PubMed PMID: 26036526. 2: Wu NC, Tong SP, Yang YC, Wang JC, Wang JJ. MK-571 attenuates kidney ischemia and reperfusion-induced airway hypersensitivity in rats. Transplant Proc. 2014 May;46(4):1127-30. doi: 10.1016/j.transproceed.2013.12.041. PubMed PMID: 24815144. 3: Takeuchi K, Shibata M, Kashiyama E, Umehara K. Expression levels of multidrug resistance-associated protein 4 (MRP4) in human leukemia and lymphoma cell lines, and the inhibitory effects of the MRP-specific inhibitor MK-571 on methotrexate distribution in rats. Exp Ther Med. 2012 Sep;4(3):524-532. Epub 2012 Jun 29. PubMed PMID: 23181130; PubMed Central PMCID: PMC3503844. 4: Rahi MM, Heikkinen TM, Hakala KE, Laine KP. The effect of probenecid and MK-571 on the feto-maternal transfer of saquinavir in dually perfused human term placenta. Eur J Pharm Sci. 2009 Jul 12;37(5):588-92. doi: 10.1016/j.ejps.2009.05.005. Epub 2009 May 18. PubMed PMID: 19454316. 5: Wong WS, Zhu H, Liao W. Cysteinyl leukotriene receptor antagonist MK-571 alters bronchoalveolar lavage fluid proteome in a mouse asthma model. Eur J Pharmacol. 2007 Dec 1;575(1-3):134-41. Epub 2007 Jul 24. PubMed PMID: 17689528. 6: Blain JF, Sirois P. Involvement of LTD(4)in allergic pulmonary inflammation in mice: modulation by cysLT(1)antagonist MK-571. Prostaglandins Leukot Essent Fatty Acids. 2000 Jun;62(6):361-8. PubMed PMID: 10913229. 7: Gök S, Onal A, Cinar MG, Evinç A. The antinociceptive effect of leukotriene D(4) receptor antagonist, MK-571, in mice: possible involvement of opioidergic mechanism. Eur J Pharmacol. 1999 Dec 15;386(2-3):195-200. PubMed PMID: 10618470. 8: Vellenga E, Tuyt L, Wierenga BJ, Müller M, Dokter W. Interleukin-6 production by activated human monocytic cells is enhanced by MK-571, a specific inhibitor of the multi-drug resistance protein-1. Br J Pharmacol. 1999 May;127(2):441-8. PubMed PMID: 10385244; PubMed Central PMCID: PMC1566046. 9: Gaddy JN, Margolskee DJ, Bush RK, Williams VC, Busse WW. Bronchodilation with a potent and selective leukotriene D4 (LTD4) receptor antagonist (MK-571) in patients with asthma. Am Rev Respir Dis. 1992 Aug;146(2):358-63. PubMed PMID: 1489125. 10: Depré M, Margolskee DJ, Van Hecken A, Hsieh JS, Buntinx A, De Schepper PJ, Rogers JD. Dose-dependent kinetics of the enantiomers of MK-571, and LTD4-receptor antagonist. Eur J Clin Pharmacol. 1992;43(4):431-3. PubMed PMID: 1451726. 11: Depré M, Margolskee DJ, Hsieh JY, Van Hecken A, Buntinx A, De Lepeleire I, Rogers JD, De Schepper PJ. Plasma drug profiles and tolerability of MK-571 (L-660,711), a leukotriene D4 receptor antagonist, in man. Eur J Clin Pharmacol. 1992;43(4):427-30. PubMed PMID: 1451725. 12: Jones TR, Zamboni R, Belley M, Champion E, Charette L, Ford-Hutchinson AW, Gauthier JY, Leger S, Lord A, Masson P, et al. Pharmacology of the leukotriene antagonist verlukast: the (R)-enantiomer of MK-571. Can J Physiol Pharmacol. 1991 Dec;69(12):1847-54. PubMed PMID: 1666333. 13: Robinett RS, Hsieh JY. Stereoselective determination of R(-)- and S(+)-MK-571, a leukotriene D4 antagonist, in human plasma by chiral high-performance liquid chromatography. J Chromatogr. 1991 Sep 18;570(1):157-65. PubMed PMID: 1797821. 14: Kips JC, Joos GF, De Lepeleire I, Margolskee DJ, Buntinx A, Pauwels RA, Van der Straeten ME. MK-571, a potent antagonist of leukotriene D4-induced bronchoconstriction in the human. Am Rev Respir Dis. 1991 Sep;144(3 Pt 1):617-21. PubMed PMID: 1892302. 15: Amirav I, Pawlowski N. Inhibition of exercise-induced bronchoconstriction by MK-571, a potent leukotriene D4-receptor antagonist. N Engl J Med. 1991 May 2;324(18):1288. PubMed PMID: 1849613. 16: McLeod JD, Piper PJ. Effect of ICI 198,615, SK+F 104,353, MK-571 and CGP45715A on cysteinyl leukotriene-induced responses in guinea-pig heart. Prostaglandins. 1991 Apr;41(4):395-406. PubMed PMID: 1871378. 17: Denzlinger C, Grimberg M, Kapp A, Haberl C, Wilmanns W. Effect of the leukotriene receptor antagonists FPL 55712, LY 163443, and MK-571 on the elimination of cysteinyl leukotrienes in the rat. Br J Pharmacol. 1991 Apr;102(4):865-70. Erratum in: Br J Pharmacol 1991 Jul;103(3):1834. PubMed PMID: 1855116; PubMed Central PMCID: PMC1917974. 18: Rasmussen JB, Margolskee DJ, Eriksson LO, Williams VC, Andersson KE. Leukotriene (LT) D4 is involved in antigen-induced asthma: a study with the LTD4 receptor antagonist, MK-571. Ann N Y Acad Sci. 1991;629:436. PubMed PMID: 1952571. 19: Ford-Hutchinson AW. Regulation of the production and action of leukotrienes by MK-571 and MK-886. Adv Prostaglandin Thromboxane Leukot Res. 1991;21A:9-16. PubMed PMID: 1847788. 20: Young RN. Development of novel leukotriene--based anti-asthma drugs: MK-886 and MK-571. Agents Actions Suppl. 1991;34:179-87. Review. PubMed PMID: 1793062. (last updated: 4/20/2016).