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Merck
CN

SML3572

MK-0524

≥98% (HPLC)

Synonym(s):

Laropiprant, MK 0524, MK0524, [(3R)-4-(4-Chloro-benzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid

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About This Item

Empirical Formula (Hill Notation):
C21H19ClFNO4S
CAS Number:
571170-77-9
Molecular Weight:
435.90
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD11042421

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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

SMILES string

OC(C[C@@H](CC1)C2=C1C3=CC(F)=CC(S(C)(=O)=O)=C3N2CC4=CC=C(C=C4)Cl)=O

InChI key

NXFFJDQHYLNEJK-CYBMUJFWSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

Quality Level

100

Biochem/physiol Actions

MK-0524 is a potent and selective prostaglandin D2 (PGD2) receptor PTGDR (DP1) antagonist with inverse agonist activity (Ki = 570 pM/DP1, 2.95 nM/TP, 745 nM/DP2, >890 nM for EP1/2/3/4, FP and IP). MK-0524 inhibits cAMP accumulation in PGD2-challenged human platelets (IC50 = 90 pM) and blocks PGD2-induced nasal congestion in a sheep allergic rhinitis model in vivo (by 99% at 0.1 mg/kg i.v.). MK-0524 decreases DP1-dependent basal cAMP level in HEK293 (1-100 nM) without affecting DP1-dependent basal ERK1/2 phosphorylation (up to 1 μM).
Potent and selective prostaglandin D2 (PGD2) receptor PTGDR (DP1) antagonist with inverse agonist activity in vitro and in vivo.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000220590
0000220591
0000208220
0000208220
0000220591

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Role of prostaglandin D2 receptors in the pathogenesis of abdominal aortic aneurysm formation
Clinical Science (London, England : 1979), 136, 309-321 (2022)
Protectin DX promotes the inflammatory resolution via activating COX-2/L-PGDS-PGD2 and DP1 receptor in acute respiratory distress syndrome
Xin Hu , Ye-An Zhang , Ben Chen, Zi Jin, Mei-Lin Lin, Ming Li, Hong-Xia Mei, Jia-Chao Lu
International Immunopharmacology, 102, 108348-108348 (2022)
Novel Evidence-Based Combination of Plant Extracts with Multitarget Mechanisms of Action for the Elimination of Hot Flashes during Menopause
Maria Tsoumani , Panagiota Efstathia Nikolaou
Biomolecules, 27, 1221-1221 (2022)
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)
Journal of medicinal chemistry, 50, 794-806 (2007)
Keisuke Obara et al.
Biological & pharmaceutical bulletin, 44(8), 1129-1139 (2021-08-03)
Docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) are n-3 polyunsaturated fatty acids (PUFAs), and are abundant in fish oil. These n-3 PUFAs have been reported to improve the lower gastrointestinal (LGI) disorders such as ulcerative colitis and Crohn's disease through
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