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
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Summary of Clinical Use Click here for help
Laropiprant was evaluated as a potential drug to reduce facial flushes induced by niacin, and to reduce the erythema associated with rosacea, but development for these indications has been discontinued. Click here to link to ClinicalTrials.gov's full list of laropiprant trials.