118414-82-7

Basic information

• Product Name: MK-886
• Synonyms: L-663,536;1-[(4-CHLOROPHENYL)METHYL]-3-[(1,1-DIMETHYLETHYL)THIO]-ALPHA,ALPHA-DIMETHYL-5-(1-METHYLETHYL)-1H-INDOLE-2-PROPANOIC ACID;MK-886;3-[tert-Butylthio-1-(4-chlorobenzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethylpropionic Acid, Sodium Salt;3-[1-(4-Chlorobenzyl)-3-(tert-butylthio)-5-isopropyl-1H-indol-2-yl]-2,2-dimethylpropanoic acid;3-[1-(4-Chlorobenzyl)-3-(tert-butylthio)-5-isopropyl-1H-indol-2-yl]-2,2-dimethylpropionic acid;3-[3-tert-Butylthio-1-(4-chlorobenzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethylpropionic acid;CGS-81585
• CAS NO: 118414-82-7
• Molecular Formula: C₂₇H₃₄ClNO₂S
• Molecular Weight: 494.07
• Product Categories: All Inhibitors;Inhibitors;Prostanoid receptor and related
• Mol File: 118414-82-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 295-297°C
• Boiling Point: 623.4°Cat760mmHg
• Flash Point: 330.8°C
• Appearance: white/
• Density: 1.14g/cm³
• Vapor Pressure: 2.11E-16mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: 2-8°C
• Solubility: DMSO: 32 mg/mL
• Stability: Stable for 1 year as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
• CAS DataBase Reference: MK-886(CAS DataBase Reference)
• NIST Chemistry Reference: MK-886(118414-82-7)
• EPA Substance Registry System: MK-886(118414-82-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 118414-82-7(Hazardous Substances Data)

Usage

Description

MK-886, also known as 1H-indole, is a chemical compound belonging to the class of indoles. It is characterized by the presence of an isopropyl group at position 5, a tert-butylsulfanediyl group at position 3, a 4-chlorobenzyl group at position 1, and a 2-carboxy-2-methylpropyl group at position 2. MK-886 acts as an inhibitor of arachidonate 5-lipoxygenase and is a potent and selective inhibitor of 5-lipoxygenase-activating protein (FLAP) and cyclooxygenase-1 (Cox-1). It is a white solid and has a high affinity for binding to FLAP, preventing the activation of 5-lipoxygenase and subsequently inhibiting the biosynthesis of leukotrienes.

Uses

1. Used in Pharmaceutical Industry:
MK-886 is used as an inhibitor for leukotriene biosynthesis due to its high affinity for binding to 5-lipoxygenase-activating protein (FLAP). This inhibition prevents the activation of 5-lipoxygenase, which in turn suppresses the biosynthesis of leukotrienes. Leukotrienes are known to play a role in various inflammatory processes, making MK-886 a potential candidate for the development of anti-inflammatory drugs.
2. Used in Research Applications:
MK-886 is used as a potent and selective inhibitor of FLAP and Cox-1 in research settings. Its ability to inhibit these proteins makes it a valuable tool for studying the roles of FLAP and Cox-1 in various biological processes and for investigating the potential therapeutic effects of targeting these proteins in the treatment of diseases.
3. Used in Drug Development:
MK-886 is used as a starting point for the development of new drugs targeting leukotriene biosynthesis and related inflammatory pathways. Its potent and selective inhibition of FLAP and Cox-1 makes it a promising candidate for the development of novel anti-inflammatory and anti-allergic medications.
4. Used in Inflammation and Allergy Treatment:
MK-886 is used as a potential therapeutic agent for the treatment of inflammation and allergy-related conditions. By inhibiting leukotriene biosynthesis, MK-886 may help to alleviate symptoms associated with these conditions and improve the overall quality of life for patients.

Biological Activity

An inhibitor of leukotriene biosynthesis (IC 50 = 3 nM in human polymorphonuclear leukocytes). Acts by inhibiting 5-lipoxygenase-activating protein (FLAP) (IC 50 = 30 nM for inhibition of [ 125 I]-L-691,678 photoaffinity labelling). Also moderately potent PPAR α antagonist (IC 50 = 0.5-1 μ M). Orally active in vivo .

References

References/Citations 1) Gillard et al (1989) L-663,536 (MK-886) (3-[1-(4-chlorobenzyl)-3-t-butyl-thio-5-isopropylindol-2-yl]-2,2-dimethylpropanoic acid), a novel, orally active leukotriene biosynthesis inhibitor; Can. .J. Physiol .Pharmacol. 67 456 2) Evans et al (1991) 5-Lipoxygenase-activating protein is the target of a quinoline class of leukotriene synthesis inhibitors; Mol. Pharmacol. 40 22 3) Kehrer et al (2001) Inhibition of peroxisome-proliferator-activated receptor (PPAR)α by MK886; Biochem. J. 356 899

InChI:InChI=1/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)

Downstream Products

• 1056599-03-1 3-[3-tert-butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethyl-propionyl chloride 
• 141862-64-8 C₂₈H₃₈ClN₃O₂S 
• 141863-05-0 N-{3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethyl-propyl}-hydroxylamine 
• 141862-63-7 3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethyl-propionaldehyde oxime 
• 118414-93-0 3-[3-tert-Butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-2-yl]-2,2-dimethyl-propionaldehyde 
• 118414-91-8 3-[1-(p-chlorobenzyl)-3-(t-butylthio)-5-(i-propyl)-indole-2-yl]-2,2-dimethylpropanol 
• 1031435-25-2 3-[3-tert-butylsulfanyl-1-(4-chloro-benzyl)-5-isopropyl-1H-indol-yl]-2,2-dimethyl-propionic acid 6-nitrooxy-hexyl ester 

Relevant articles and documents

3-hetero-substituted-n-benzyl-indoles and prevention of leucotriene synthesis therewith

Compounds having the formula: STR1 are inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents. They are also useful in treating diarrhea, hypertension, angina, platelet aggregation, cerebral spasm, premature labor, spontaneous abortion, dysmenorrhea, and migraine.