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SML3572

Sigma-Aldrich

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
MDL number:
MFCD11042421
UNSPSC Code:
12352200
NACRES:
NA.77
Pricing and availability is not currently available.

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

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

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

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 Code

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
0000208220
0000220591
0000220590

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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)
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)
Role of prostaglandin D2 receptors in the pathogenesis of abdominal aortic aneurysm formation
Clinical Science (London, England : 1979), 136, 309-321 (2022)
Yaqun Li et al.
The Korean journal of pain, 34(1), 27-34 (2021-01-01)
Chemotherapy-induced peripheral neuropathy (CIPN) is a major reason for stopping or changing anticancer therapy. Among the proposed pathomechanisms underlying CIPN, proinflammatory processes have attracted increasing attention. Here we assessed the role of prostaglandin D2 (PGD2) signaling in cisplatin-induced neuropathic pain.
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)
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