laropiprant   Click here for help

GtoPdb Ligand ID: 3356

Synonyms: MK-0524 | MK0524
Compound class: Synthetic organic
Comment: Laropiprant is an orally active prostanoid DP1 receptor antagonist [2]. It inhibits niacin-induced vasodilation [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 84.75
Molecular weight 435.07
XLogP 4.13
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)CC1CCc2c1n(Cc1ccc(cc1)Cl)c1c2cc(cc1S(=O)(=O)C)F
Isomeric SMILES OC(=O)C[C@H]1CCc2c1n(Cc1ccc(cc1)Cl)c1c2cc(cc1S(=O)(=O)C)F
InChI InChI=1S/C21H19ClFNO4S/c1-29(27,28)18-10-15(23)9-17-16-7-4-13(8-19(25)26)20(16)24(21(17)18)11-12-2-5-14(22)6-3-12/h2-3,5-6,9-10,13H,4,7-8,11H2,1H3,(H,25,26)/t13-/m1/s1
InChI Key NXFFJDQHYLNEJK-CYBMUJFWSA-N
References
1. Cheng K, Wu TJ, Wu KK, Sturino C, Metters K, Gottesdiener K, Wright SD, Wang Z, O'Neill G, Lai E et al.. (2006)
Antagonism of the prostaglandin D2 receptor 1 suppresses nicotinic acid-induced vasodilation in mice and humans.
Proc Natl Acad Sci USA, 103 (17): 6682-7. [PMID:16617107]
2. Sturino CF, O'Neill G, Lachance N, Boyd M, Berthelette C, Labelle M, Li L, Roy B, Scheigetz J, Tsou N et al.. (2007)
Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chloro-benzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524).
J Med Chem, 50 (4): 794-806. [PMID:17300164]