laropiprant

Laropiprant (INN) was a drug used in combination with nicotinic acid to reduce blood cholesterol (LDL and VLDL) that is no longer sold, due to increases in side-effects with no cardiovascular benefit. Laropiprant itself has no cholesterol lowering effect, but it reduces facial flushes induced by nicotinic acid.

Chemical data

Formula: C21H19ClFNO4S
Molecular weight: 435.9 g/mol
IUPAC name: 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid

via PubChem

Drug data · ChEMBL

Withdrawn

Max clinical phase: Approved
Molecule type: Small molecule
Indications: rosacea, Hypercholesterolemia, familial hypercholesterolemia, Disorder of lipid metabolism

via ChEMBL · EBI

Wikidata facts

Mass: 435.07073498799997

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chemical formula: C₂₁H₁₉ClFNO₄S
canonical SMILES: CS(=O)(=O)C1=C2C(=CC(=C1)F)C3=C(N2CC4=CC=C(C=C4)Cl)C(CC3)CC(=O)O
isomeric SMILES: CS(=O)(=O)c1cc(cc2c1n(c3c2CC[C@@H]3CC(=O)O)Cc4ccc(cc4)Cl)F
Commons category: Laropiprant

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Article

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Contents

Mechanism of action
History
References

Merck & Co. planned to market this combination under the trade names Cordaptive in the US and Tredaptive in Europe. Both brands contained 1000 mg of nicotinic acid (niacin) and 20 mg of laropiprant in each tablet.