Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C26H26ClN2O3S2.Na |
| Molecular Weight | 537.069 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CN(C)C(=O)CCSC(SCCC([O-])=O)C1=CC=CC(\C=C\C2=NC3=CC(Cl)=CC=C3C=C2)=C1
InChI
InChIKey=XNAYQOBPAXEYLI-AAGWESIMSA-M
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+;
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C26H26ClN2O3S2 |
| Molecular Weight | 514.079 |
| Charge | -1 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Optical Activity | ( + / - ) |
MK-571 is a selective, orally active leukotriene D4/E4 (LTD4/E4) receptor antagonist patented by Merck Frosst Canada, Inc. for the treatment bronchoconstriction. In ex vivo models MK-571 competitively antagonizes contractions of guinea pig trachea and ileum induced by leukotriene (LT) D4 and LTE4 and contractions of human trachea induced by LTD4. MK-571 antagonizes bronchoconstriction induced in anesthetized guinea pigs by i.v. LTC4, LTD4, and LTE4 but do not block bronchoconstriction to arachidonic acid. In clinical trials, MK-571 is a potent antagonist of LTD4-induced bronchoconstriction in both normal volunteers and asthmatic patients.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of the leukotriene receptor antagonist MK-0679 on baseline pulmonary function in aspirin sensitive asthmatic subjects. | 1993 Dec |
|
| Characterization of the leukotriene D4 receptor in dimethylsulphoxide-differentiated U937 cells: comparison with the leukotriene D4 receptor in human lung and guinea-pig lung. | 1993 Feb 15 |
|
| Leukotriene D4-induced increases in cytosolic calcium in THP-1 cells: dependence on extracellular calcium and inhibition with selective leukotriene D4 receptor antagonists. | 1994 Jun |
|
| Adenosine triphosphate-dependent transport of anionic conjugates by the rabbit multidrug resistance-associated protein Mrp2 expressed in insect cells. | 1998 Jun |
|
| Overexpression of glutathione S-transferase II and multidrug resistance transport proteins is associated with acquired tolerance to inorganic arsenic. | 2001 Aug |
|
| Synergistic antiallergic activity of combined histamine H1- and cysteinyl leukotriene1-receptor blockade in human bronchus. | 2001 May 11 |
|
| Molecular cloning and functional characterization of murine cysteinyl-leukotriene 1 (CysLT(1)) receptors. | 2001 Nov 1 |
|
| Functional analysis of ABCA8, a new drug transporter. | 2002 Oct 18 |
|
| Leukotrienes mediate murine bronchopulmonary hyperreactivity, inflammation, and part of mucosal metaplasia and tissue injury induced by recombinant murine interleukin-13. | 2003 Apr |
|
| Carboxylesterase-mediated sensitization of human tumor cells to CPT-11 cannot override ABCG2-mediated drug resistance. | 2003 Aug |
|
| Blockage of multidrug resistance-associated proteins potentiates the inhibitory effects of arsenic trioxide on CYP1A1 induction by polycyclic aromatic hydrocarbons. | 2003 Jan |
|
| Toxicity of human monocytic THP-1 cells and microglia toward SH-SY5Y neuroblastoma cells is reduced by inhibitors of 5-lipoxygenase and its activating protein FLAP. | 2003 Mar |
|
| Functional expression of the multidrug resistance protein 1 in microglia. | 2003 Oct |
|
| Leukotrienes mediate part of Ova-induced lung effects in mice via EGFR. | 2003 Oct |
|
| Inverse agonist activity of selected ligands of the cysteinyl-leukotriene receptor 1. | 2004 Apr |
|
| Structural requirements for the flavonoid-mediated modulation of glutathione S-transferase P1-1 and GS-X pump activity in MCF7 breast cancer cells. | 2004 Apr 15 |
|
| Identification of multidrug resistance-associated protein 1 and glutathione as multidrug resistance mechanisms in human prostate cancer cells: chemosensitization with leukotriene D4 antagonists and buthionine sulfoximine. | 2004 Jun |
|
| Substrates and inhibitors of efflux proteins interfere with the MTT assay in cells and may lead to underestimation of drug toxicity. | 2004 Oct |
|
| The human multidrug-resistance-associated protein MRP1 mediates ATP-dependent transport of unconjugated bilirubin. | 2004 Oct 15 |
|
| Determination of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid and its acyl glucuronide in Caco-2 monolayers by liquid chromatography with fluorescence detection: application to transport studies. | 2004 Sep 25 |
|
| Expression and activity of multidrug resistance protein 1 in a murine thymoma cell line. | 2005 Apr |
|
| Modulation of MRP1 protein transport by plant, and synthetically modified flavonoids. | 2005 Aug 26 |
|
| Inhibitory activity of a green tea extract and some of its constituents on multidrug resistance-associated protein 2 functionality. | 2005 Feb |
|
| MRP-1 expression levels determine strain-specific susceptibility to sodium arsenic-induced renal injury between C57BL/6 and BALB/c mice. | 2005 Feb 15 |
|
| Endogenous thiols and MRP transporters contribute to Hg2+ efflux in HgCl2-treated tubular MDCK cells. | 2005 Jan 5 |
|
| Combined effects of GSTP1 and MRP1 in melanoma drug resistance. | 2005 Jul 25 |
|
| Mrp2/Abcc2 transport activity is stimulated by protein kinase Calpha in a baculo virus co-expression system. | 2005 Jun 17 |
|
| Catfish egg lectin causes rapid activation of multidrug resistance 1 P-glycoprotein as a lipid translocase. | 2005 Mar |
|
| Cysteinyl leukotrienes mediate the enhancing effects of indomethacin and aspirin on eosinophil production in murine bone marrow cultures. | 2008 Feb |
|
| Montelukast is a potent and durable inhibitor of multidrug resistance protein 2-mediated efflux of taxol and saquinavir. | 2009 Dec |
|
| CYP1A1 induction and CYP3A4 inhibition by the fungicide imazalil in the human intestinal Caco-2 cells-comparison with other conazole pesticides. | 2009 Feb 10 |
|
| Cross-functioning between the extraneuronal monoamine transporter and multidrug resistance protein 1 in the uptake of adrenaline and export of 5-(glutathion-S-yl)adrenaline in rat cardiomyocytes. | 2009 Jan |
|
| ABCC1, ABCC2 and ABCC3 are implicated in the transepithelial transport of the myco-estrogen zearalenone and its major metabolites. | 2009 Oct 28 |
|
| Culture period-dependent change of function and expression of ATP-binding cassette transporters in Caco-2 cells. | 2009 Sep |
|
| Multidrug resistance protein transporter and Ins(1,4,5)P₃-sensitive Ca²+-signaling involved in adenosine triphosphate export via Gq protein-coupled NK₂-receptor stimulation with neurokinin A. | 2010 |
|
| MRP transporters as membrane machinery in the bradykinin-inducible export of ATP. | 2010 Apr |
|
| Chrysin blocks topotecan-induced apoptosis in Caco-2 cells in spite of inhibition of ABC-transporters. | 2010 Aug 15 |
|
| Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. | 2010 Dec |
|
| Multidrug resistance proteins restrain the intestinal absorption of trans-resveratrol in rats. | 2010 Mar |
|
| Differential disposition of chenodeoxycholic acid versus taurocholic acid in response to acute troglitazone exposure in rat hepatocytes. | 2011 Apr |
|
| Multidrug resistance-associated protein 1 mediates 15-deoxy-Δ(12,14)-prostaglandin J2-induced expression of glutamate cysteine ligase expression via Nrf2 signaling in human breast cancer cells. | 2011 Aug 15 |
|
| Molecular characterization and functions of zebrafish ABCC2 in cellular efflux of heavy metals. | 2011 May |
|
| Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). | 2013 Dec |
|
| The role of efflux transporters on the transport of highly toxic aconitine, mesaconitine, hypaconitine, and their hydrolysates, as determined in cultured Caco-2 and transfected MDCKII cells. | 2013 Feb 4 |
|
| Transcellular transport of aconitine across human intestinal Caco-2 cells. | 2013 Jul |
|
| Arsenate accumulation and arsenate-induced glutathione export in astrocyte-rich primary cultures. | 2013 Jun |
|
| Multidrug resistance protein 1 (ABCC1) confers resistance to arsenic compounds in human myeloid leukemic HL-60 cells. | 2013 Jun |
|
| A multifactorial approach to hepatobiliary transporter assessment enables improved therapeutic compound development. | 2013 Nov |
|
| Utilization of human nuclear receptors as an early counter screen for off-target activity: a case study with a compendium of 615 known drugs. | 2015 Jun |
|
| Nrf2 Regulates the Sensitivity of Mouse Keratinocytes to Nitrogen Mustard via Multidrug Resistance-Associated Protein 1 (Mrp1). | 2016 Jan |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 09:00:23 GMT 2023
by
admin
on
Sat Dec 16 09:00:23 GMT 2023
|
| Record UNII |
4238L635XD
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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DTXSID5046358
Created by
admin on Sat Dec 16 09:00:23 GMT 2023 , Edited by admin on Sat Dec 16 09:00:23 GMT 2023
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115103-85-0
Created by
admin on Sat Dec 16 09:00:23 GMT 2023 , Edited by admin on Sat Dec 16 09:00:23 GMT 2023
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16760569
Created by
admin on Sat Dec 16 09:00:23 GMT 2023 , Edited by admin on Sat Dec 16 09:00:23 GMT 2023
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4238L635XD
Created by
admin on Sat Dec 16 09:00:23 GMT 2023 , Edited by admin on Sat Dec 16 09:00:23 GMT 2023
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PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET -> INHIBITOR |
Binding Assy
IC50
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