571170-77-9

571170-77-9 structure

Name: Laropiprant
Chemical Name: 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid
CAS Number: 571170-77-9
Molecular Formula: C₂₁H₁₉ClFNO₄S
Molecular Weight: 435.896
Catalog: Signaling Pathways GPCR/G Protein Prostaglandin Receptor
Create Date: 2018-04-14 08:00:00
Modify Date: 2024-01-14 09:43:14
Laropiprant is a potent, selective DP receptor antagonist with Ki values of 0.57 nM and 2.95 nM for DP receptor and TP Receptor, respectively.

Name	2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid
Synonyms	Laropiprant Laropiprant (INN/USAN) Cyclopent[b]indole-3-acetic acid, 4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3R)- [(3R)-4-(4-chlorophenyl)methyl-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b] indol-3-yl]acetic acid (3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta(b)indol-3-yl acetic acid cc-711 (3R)-[4-(4-chlorobenzyl)-7-fluoro-5-(methane-sulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid (-)-[4-(4-chlorobenzyl)-7-fluoro-5-(methanesulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]-indol-3-yl]acetic acid MFCD11042421 [(3R)-4-(4-Chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid [14C]-Laropiprant MK 0524 UNII-G7N11T8O78 MK-0524

Description	Laropiprant is a potent, selective DP receptor antagonist with Ki values of 0.57 nM and 2.95 nM for DP receptor and TP Receptor, respectively.
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Prostaglandin Receptor Research Areas >> Inflammation/Immunology
Target	DP/DP1 Receptor:0.57 nM (Ki) TP Receptor:2.95 nM (Ki)
In Vitro	Laropiprant is a potent, selective DP receptor antagonist with Ki values of 0.57 nM and 2.95 nM for DP receptor and TP Receptor, respectively.[1]. Laropiprant (1 µM) causes a significant inhibition of the aggregation but still counteractes the pronounced inhibition caused by PGD2 (30 nM) and BW245c (3 nM). Laropiprant blocks DP receptor-dependent increase in VASP phosphorylation, as well as inhibition of P-selectin expression, GPIIb/IIIa activation and in vitro thrombus formation. Laropiprant antagonizes the increased platelet aggregation by TP and EP3 receptor activation. Laropiprant (10 µM) and niacin inhibit in vitro thrombus formation[2].
Cell Assay	Vena8Fluoro+ Biochips are coated with collagen (200 µg/mL) at 4°C overnight and thereafter blocked with bovine serum albumin (10 µg/mL) for 30 minutes at room temperature followed by washing steps. Whole blood collected in sodium citrate is incubated with 3, 3-dihexyloxacarbocyanine iodide (1 µM) in the dark for 10 minutes. PGD2 (30 nM), BW245c (3 nM) are added 10 min before the start of perfusion, and the DP antagonist BWA868c or Laropiprant (1 µM) are added 10 min before the agonists. In another set of experiments whole blood is treated with niacin (3 mM), acetylsalicylic acid (1 mM) or Laropiprant (1 µM and 10 µM) for 30 min. CaCl2 at a final concentration of 1 mM is added 2 minutes before the perfusion over the collagen-coated chip. Perfusion is carried out at a shear rate of 30 dynes cm2. Thrombus formation is recorded. Computerized image analysis is performed by DucoCell analysis software, where the area covered by the thrombus is calculated. Data are expressed as percent of area covered in a control sample[2].
References	[1]. Sturino CF, et al. 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. 2007 Feb 22;50(4):794-806. [2]. Philipose S, et al. Laropiprant Attenuates EP3 and TP Prostanoid Receptor-Mediated Thrombus Formation. PLoS One. 2012;7(8):e40222.

Density	1.5±0.1 g/cm3
Boiling Point	710.0±60.0 °C at 760 mmHg
Melting Point	175∶ºC
Molecular Formula	C₂₁H₁₉ClFNO₄S
Molecular Weight	435.896
Flash Point	383.2±32.9 °C
Exact Mass	435.070740
PSA	84.75000
LogP	3.82
Vapour Pressure	0.0±2.4 mmHg at 25°C
Index of Refraction	1.664
Storage condition	-20°C