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Details

Stereochemistry RACEMIC
Molecular Formula C26H27ClN2O3S2
Molecular Weight 515.087
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(SCCC(O)=O)C1=CC=CC(\C=C\C2=CC=C3C=CC(Cl)=CC3=N2)=C1

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 515.087
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
Adenosine triphosphate-dependent transport of anionic conjugates by the rabbit multidrug resistance-associated protein Mrp2 expressed in insect cells.
1998 Jun
Characterization of the human cysteinyl leukotriene CysLT1 receptor.
1999 Jun 24
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
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
Expression and activity of multidrug resistance protein 1 in a murine thymoma cell line.
2005 Apr
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
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
Role of proline 1150 in functional interactions between the membrane spanning domains and nucleotide binding domains of the MRP1 (ABCC1) transporter.
2008 Apr 15
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
ABCC1, ABCC2 and ABCC3 are implicated in the transepithelial transport of the myco-estrogen zearalenone and its major metabolites.
2009 Oct 28
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
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
Patents

Patents

Sample Use Guides

1,500, 86, or 28 mg
Route of Administration: Intravenous
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:14:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:14:33 GMT 2025
Record UNII
76LB1G2X6V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MK-571
Common Name English
L 660711
Preferred 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
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 Mon Mar 31 18:14:33 GMT 2025 , Edited by admin on Mon Mar 31 18:14:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID5048390
Created by admin on Mon Mar 31 18:14:33 GMT 2025 , Edited by admin on Mon Mar 31 18:14:33 GMT 2025
PRIMARY
PUBCHEM
5281888
Created by admin on Mon Mar 31 18:14:33 GMT 2025 , Edited by admin on Mon Mar 31 18:14:33 GMT 2025
PRIMARY
CAS
115104-28-4
Created by admin on Mon Mar 31 18:14:33 GMT 2025 , Edited by admin on Mon Mar 31 18:14:33 GMT 2025
PRIMARY
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