Ligand id: 6696

Name: darapladib

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 15
Topological polar surface area 81.19
Molecular weight 667.27
XLogP 10.29
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

1. Blackie JA, Bloomer JC, Brown MJ, Cheng HY, Hammond B, Hickey DM, Ife RJ, Leach CA, Lewis VA, Macphee CH et al.. (2003)
The identification of clinical candidate SB-480848: a potent inhibitor of lipoprotein-associated phospholipase A2.
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2. Mohler 3rd ER, Ballantyne CM, Davidson MH, Hanefeld M, Ruilope LM, Johnson JL, Zalewski A, Darapladib Investigators. (2008)
The effect of darapladib on plasma lipoprotein-associated phospholipase A2 activity and cardiovascular biomarkers in patients with stable coronary heart disease or coronary heart disease risk equivalent: the results of a multicenter, randomized, double-blind, placebo-controlled study.
J. Am. Coll. Cardiol.51 (17): 1632-41. [PMID:18436114]
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Study design and rationale for the Stabilization of pLaques usIng Darapladib-Thrombolysis in Myocardial Infarction (SOLID-TIMI 52) trial in patients after an acute coronary syndrome.
Am. Heart J.162 (4): 613-619.e1. [PMID:21982651]
4. O'Donoghue ML, Braunwald E, White HD, Steen DP, Lukas MA, Tarka E, Steg PG, Hochman JS, Bode C, Maggioni AP et al.. (2014)
Effect of darapladib on major coronary events after an acute coronary syndrome: the SOLID-TIMI 52 randomized clinical trial.
JAMA312 (10): 1006-15. [PMID:25173516]
5. Sofogianni A, Alkagiet S, Tziomalos K. (2018)
Lipoprotein-associated phospholipase A2 and coronary heart disease.
Curr. Pharm. Des.,  [Epub ahead of print]. [PMID:29332572]
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Darapladib for preventing ischemic events in stable coronary heart disease.
N. Engl. J. Med.370 (18): 1702-11. [PMID:24678955]
7. Staurenghi G, Ye L, Magee MH, Danis RP, Wurzelmann J, Adamson P, McLaughlin MM, Darapladib DME Study Group. (2015)
Darapladib, a lipoprotein-associated phospholipase A2 inhibitor, in diabetic macular edema: a 3-month placebo-controlled study.
Ophthalmology122 (5): 990-6. [PMID:25749297]
8. Tian Y, Jia H, Li S, Wu Y, Guo L, Tan G, Li B. (2017)
The associations of stroke, transient ischemic attack, and/or stroke-related recurrent vascular events with Lipoprotein-associated phospholipase A2: A systematic review and meta-analysis.
Medicine (Baltimore)96 (51): e9413. [PMID:29390564]
9. Tjoelker LW, Wilder C, Eberhardt C, Stafforini DM, Dietsch G, Schimpf B, Hooper S, Le Trong H, Cousens LS, Zimmerman GA et al.. (1995)
Anti-inflammatory properties of a platelet-activating factor acetylhydrolase.
Nature374 (6522): 549-53. [PMID:7700381]
10. Wilensky RL, Macphee CH. (2009)
Lipoprotein-associated phospholipase A(2) and atherosclerosis.
Curr. Opin. Lipidol.20 (5): 415-20. [PMID:19667981]
11. Woolford AJ, Day PJ, Bénéton V, Berdini V, Coyle JE, Dudit Y, Grondin P, Huet P, Lee LY, Manas ES et al.. (2016)
Fragment-Based Approach to the Development of an Orally Bioavailable Lactam Inhibitor of Lipoprotein-Associated Phospholipase A2 (Lp-PLA2).
J. Med. Chem.59 (23): 10738-10749. [PMID:27933945]