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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
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
Characterization of the human cysteinyl leukotriene 2 receptor.
2000 Sep 29
Overexpression of glutathione S-transferase II and multidrug resistance transport proteins is associated with acquired tolerance to inorganic arsenic.
2001 Aug
Functional analysis of ABCA8, a new drug transporter.
2002 Oct 18
Functional expression of the multidrug resistance protein 1 in microglia.
2003 Oct
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
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
Combined effects of GSTP1 and MRP1 in melanoma drug resistance.
2005 Jul 25
Catfish egg lectin causes rapid activation of multidrug resistance 1 P-glycoprotein as a lipid translocase.
2005 Mar
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
Role of proline 1150 in functional interactions between the membrane spanning domains and nucleotide binding domains of the MRP1 (ABCC1) transporter.
2008 Apr 15
CYP1A1 induction and CYP3A4 inhibition by the fungicide imazalil in the human intestinal Caco-2 cells-comparison with other conazole pesticides.
2009 Feb 10
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
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
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
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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