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

MedKoo CAT#: 326735

CAS#: 147030-01-1 (sodium)

Description: Quiflapon, also known as MK 0591, is a potent and selective 5-Lipoxygenase-activating protein (FLAP) inhibitor. MK-0591 is also a potent inhibitor of leukotriene (LT) biosynthesis in intact human and elicited rat polymorphonuclear leukocytes (PMNLs) (IC50 values 3.1 and 6.1 nM, respectively) and in human, squirrel monkey, and rat whole blood (IC50 values 510, 69, and 9 nM, respectively). MK-0591 has a high affinity for 5-lipoxygenase activating protein (FLAP) as evidenced by an IC50 value of 1.6 nM in a FLAP binding assay.


Price and Availability

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Price

10mg
USD 390
Size
Price

Size
Price

Quiflapon sodium, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 326735
Name: Quiflapon sodium
CAS#: 147030-01-1 (sodium)
Chemical Formula: C34H34ClN2NaO3S
Exact Mass: 586.2057
Molecular Weight: 609.1568
Elemental Analysis: C, 67.04; H, 5.63; Cl, 5.82; N, 4.60; Na, 3.77; O, 7.88; S, 5.26


Related CAS #: 136668-42-3 (free base)   147030-01-1 (sodium)    

Synonym: MK 0591; MK-0591; MK0591; L 686708; L-686,708; MK 591; MK591; MK-591; Quiflapon.

IUPAC/Chemical Name: sodium 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoate

InChi Key: YPURUCMVRRNPHJ-UHFFFAOYSA-M

InChi Code: InChI=1S/C34H35ClN2O3S.Na/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);/q;+1/p-1

SMILES Code: O=C(C(C)(CC(N1CC2=CC=C(C=C2)Cl)=C(C3=C1C=CC(OCC4=NC5=CC=CC=C5C=C4)=C3)SC(C)(C)C)C)O[Na]


Technical Data

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

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).

Harmonized System Code:
293490


References

1: Park MS, Sohn MH, Kim KE, Park MS, Namgung R, Lee C. 5-Lipoxygenase-activating protein (FLAP) inhibitor MK-0591 prevents aberrant alveolarization in newborn mice exposed to 85% oxygen in a dose- and time-dependent manner. Lung. 2011 Feb;189(1):43-50. doi: 10.1007/s00408-010-9264-1. Epub 2010 Nov 5. PubMed PMID: 21052705.

2: Khougaz K, Clas SD. Crystallization inhibition in solid dispersions of MK-0591 and poly(vinylpyrrolidone) polymers. J Pharm Sci. 2000 Oct;89(10):1325-34. PubMed PMID: 10980507.

3: Depré M, Van Hecken A, Verbesselt R, De Lepeleire I, Schwartz J, Porras A, Larson P, Lin C, De Schepper PJ. Pharmacokinetic and pharmacodynamic interaction

between the lipoxygenase inhibitor MK-0591 and the cyclooxygenase inhibitor ibuprofen in man. Int J Clin Pharmacol Res. 1998;18(2):53-61. PubMed PMID: 9675622.

4: Uematsu T, Kanamaru M, Kosuge K, Hara K, Uchiyama N, Takenaga N, Tanaka W, Friedman BS, Nakashima M. Pharmacokinetic and pharmacodynamic analysis of a novel leukotriene biosynthesis inhibitor, MK-0591, in healthy volunteers. Br J Clin Pharmacol. 1995 Jul;40(1):59-66. PubMed PMID: 8527269; PubMed Central PMCID: PMC1365028.

5: Hillingsø J, Kjeldsen J, Laursen LS, Lauritsen K, von Spreckelsen S, Depré M,

Friedman BS, Malmström K, Shingo S, Bukhave K, et al. Blockade of leukotriene production by a single oral dose of MK-0591 in active ulcerative colitis. Clin Pharmacol Ther. 1995 Mar;57(3):335-41. PubMed PMID: 7697951.

6: Becker AB, Black C, Lilley MK, Bajwa K, Ford-Hutchinson AW, Simons FE, Tagari

P. Antiasthmatic effects of a leukotriene biosynthesis inhibitor (MK-0591) in allergic dogs. J Appl Physiol (1985). 1995 Feb;78(2):615-22. PubMed PMID: 7759431.

7: Diamant Z, Timmers MC, van der Veen H, Friedman BS, De Smet M, Depré M, Hilliard D, Bel EH, Sterk PJ. The effect of MK-0591, a novel 5-lipoxygenase activating protein inhibitor, on leukotriene biosynthesis and allergen-induced airway responses in asthmatic subjects in vivo. J Allergy Clin Immunol. 1995 Jan;95(1 Pt 1):42-51. PubMed PMID: 7822663.

8: Depré M, Friedman B, Van Hecken A, de Lepeleire I, Tanaka W, Dallob A, Shingo

S, Porras A, Lin C, de Schepper PJ. Pharmacokinetics and pharmacodynamics of multiple oral doses of MK-0591, a 5-lipoxygenase-activating protein inhibitor. Clin Pharmacol Ther. 1994 Jul;56(1):22-30. PubMed PMID: 8033491.

9: Stevens WH, Lane CG, Woolley MJ, Ellis R, Tagari P, Black C, Ford-Hutchinson A, O'Byrne PM. Effect of FLAP antagonist MK-0591 on leukotriene production and ozone-induced airway responses in dogs. J Appl Physiol (1985). 1994 Apr;76(4):1583-8. PubMed PMID: 8045835.

10: Tagari P, Becker A, Brideau C, Frenette R, Sadl V, Thomas E, Vickers P, Ford-Hutchinson A. Leukotriene generation and metabolism in dogs: inhibition of biosynthesis by MK-0591. J Pharmacol Exp Ther. 1993 Apr;265(1):416-25. PubMed PMID: 8386242.

11: Prasit P, Belley M, Blouin M, Brideau C, Chan C, Charleson S, Evans JF, Frenette R, Gauthier JY, Guay J, et al. A new class of leukotriene biosynthesis inhibitor: the development of MK-0591. J Lipid Mediat. 1993 Mar-Apr;6(1-3):239-44. PubMed PMID: 8357985.

12: Ménard L, Laviolette M, Borgeat P. Studies of the inhibitory activity of MK-0591 (3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(quinolin-2-yl-methoxy)-indol- 2-yl]-2,2-dimethyl propanoic acid) on arachidonic acid metabolism in human phagocytes. Can J Physiol Pharmacol. 1992 Jun;70(6):808-13. PubMed PMID: 1423024.

13: Brideau C, Chan C, Charleson S, Denis D, Evans JF, Ford-Hutchinson AW, Fortin R, Gillard JW, Guay J, Guévremont D, 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. 1992 Jun;70(6):799-807. PubMed PMID: 1330258.