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Details

Stereochemistry RACEMIC
Molecular Formula C26H27ClN2O3S2
Molecular Weight 515.0903
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of MK-571

SMILES

CN(C)C(=O)CCSC(c1cccc(/C(/[H])=C(\[H])/c2ccc3ccc(cc3n2)Cl)c1)SCCC(=O)O

InChI

InChIKey=AXUZQJFHDNNPFG-UXBLZVDNSA-N
InChI=1S/C26H27ClN2O3S2/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)/b10-6+

HIDE SMILES / InChI

Molecular Formula C26H27ClN2O3S2
Molecular Weight 515.0903
Charge 0
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9Y271
Gene ID: 10800.0
Gene Symbol: CYSLTR1
Target Organism: Homo sapiens (Human)
22.0 nM [EC50]
Target ID: P08183
Gene ID: 5243.0
Gene Symbol: ABCB1
Target Organism: Homo sapiens (Human)
PubMed

PubMed

TitleDatePubMed
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 the multidrug resistance-associated protein (MRP1) in human heavy metal-selected tumor cells.
1999 Jan 29
Characterization of the human cysteinyl leukotriene CysLT1 receptor.
1999 Jun 24
Resistance of human multidrug resistance-associated protein 1-overexpressing lung tumor cells to the anticancer drug arsenic trioxide.
2001 Jun 1
Molecular cloning and functional characterization of murine cysteinyl-leukotriene 1 (CysLT(1)) receptors.
2001 Nov 1
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
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
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
Interactions of mefloquine with ABC proteins, MRP1 (ABCC1) and MRP4 (ABCC4) that are present in human red cell membranes.
2005 Aug 15
Modulation of MRP1 protein transport by plant, and synthetically modified flavonoids.
2005 Aug 26
Endogenous thiols and MRP transporters contribute to Hg2+ efflux in HgCl2-treated tubular MDCK cells.
2005 Jan 5
Effects of fibrates on human organic anion-transporting polypeptide 1B1-, multidrug resistance protein 2- and P-glycoprotein-mediated transport.
2005 Jul
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
Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5).
2005 Sep
Inhibition of MRP1-mediated efflux in human erythrocytes by mono-anionic bile salts.
2005 Sep-Oct
Involvement of P-glycoprotein and MRP1 in resistance to cyclic tetrapeptide subfamily of histone deacetylase inhibitors in the drug-resistant osteosarcoma and Ewing's sarcoma cells.
2006 Jan 1
Pharmacological inhibition of leukotrienes in an animal model of bleomycin-induced acute lung injury.
2006 Nov 21
Glutathione depletion is necessary for apoptosis in lymphoid cells independent of reactive oxygen species formation.
2007 Oct 19
Role of proline 1150 in functional interactions between the membrane spanning domains and nucleotide binding domains of the MRP1 (ABCC1) transporter.
2008 Apr 15
Cysteinyl leukotrienes mediate the enhancing effects of indomethacin and aspirin on eosinophil production in murine bone marrow cultures.
2008 Feb
A novel arsenical has antitumor activity toward As2O3-resistant and MRP1/ABCC1-overexpressing cell lines.
2008 Oct
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
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
Multidrug resistance protein 1 (ABCC1) confers resistance to arsenic compounds in human myeloid leukemic HL-60 cells.
2013 Jun
Nrf2 Regulates the Sensitivity of Mouse Keratinocytes to Nitrogen Mustard via Multidrug Resistance-Associated Protein 1 (Mrp1).
2016 Jan
Patents

Patents

Sample Use Guides

1,500, 86, or 28 mg
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:00:05 UTC 2021
Edited
by admin
on Sat Jun 26 16:00:05 UTC 2021
Record UNII
76LB1G2X6V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MK-571
Common Name English
L-660,711
Code English
PROPANOIC ACID, 3-(((3-(2-(7-CHLORO-2-QUINOLINYL)ETHENYL)PHENYL)((3-(DIMETHYLAMINO)-3-OXOPROPYL)THIO)METHYL)THIO)-, (E)-
Common Name English
MK 571
Code English
L-660711
Code English
(3-(3-(2-(7-CHLORO-2-QUINOLINYL)ETHENYL)PHENYL) ((3-DIMETHYL AMINO-3-OXO PROPYL)THIO)METHYL)THIO)PROPANOIC ACID
Common Name English
L 660711
Code English
PROPANOIC ACID, 3-(((3-((1E)-2-(7-CHLORO-2-QUINOLINYL)ETHENYL)PHENYL)((3-(DIMETHYLAMINO)-3-OXOPROPYL)THIO)METHYL)THIO)-
Common Name English
Code System Code Type Description
FDA UNII
76LB1G2X6V
Created by admin on Sat Jun 26 16:00:05 UTC 2021 , Edited by admin on Sat Jun 26 16:00:05 UTC 2021
PRIMARY
EPA CompTox
115104-28-4
Created by admin on Sat Jun 26 16:00:05 UTC 2021 , Edited by admin on Sat Jun 26 16:00:05 UTC 2021
PRIMARY
PUBCHEM
5281888
Created by admin on Sat Jun 26 16:00:05 UTC 2021 , Edited by admin on Sat Jun 26 16:00:05 UTC 2021
PRIMARY
CAS
115104-28-4
Created by admin on Sat Jun 26 16:00:05 UTC 2021 , Edited by admin on Sat Jun 26 16:00:05 UTC 2021
PRIMARY
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