CAS 571170-77-9|Laropiprant
Introduction：Basic information about CAS 571170-77-9|Laropiprant, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Laropiprant | ||
|---|---|---|---|
| CAS Number | 571170-77-9 | Molecular Weight | 435.896 |
| Density | 1.5±0.1 g/cm3 | Boiling Point | 710.0±60.0 °C at 760 mmHg |
| Molecular Formula | C21H19ClFNO4S | Melting Point | 175∶ºC |
| MSDS | / | Flash Point | 383.2±32.9 °C |
Names
| Name | 2-[(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1H-cyclopenta[b]indol-3-yl]acetic acid |
|---|---|
| Synonym | More Synonyms |
Laropiprant BiologicalActivity
| 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 ReceptorResearch 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. |
Chemical & Physical Properties
| 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 |
| InChIKey | NXFFJDQHYLNEJK-CYBMUJFWSA-N |
| SMILES | CS(=O)(=O)c1cc(F)cc2c3c(n(Cc4ccc(Cl)cc4)c12)C(CC(=O)O)CC3 |
| Storage condition | -20°C |
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 |
