A potent, selective DP1 receptor antagonist
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MK-0524

Item No. 10009835

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3R)-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-cyclopent[b]indole-3-acetic acid
CAS Number
571170-77-9
Synonyms
  • Laropiprant
Molecular Formula
C21H19ClFNO4S
Formula Weight
435.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
222, 243, 311 nm
SMILES
FC1=CC2=C(N(CC3=CC=C(Cl)C=C3)C4=C2CC[C@@H]4CC(O)=O)C(S(C)(=O)=O)=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $63

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    5 mg

    $153

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    10 mg

    $274

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    25 mg

    $602

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    Product Description

    MK-0524 is a potent, selective prostaglandin D2 (PGD2) receptor DP1 antagonist with Ki values of 0.57 nM and 0.75 µM for the DP1 and DP2 receptors, respectively.1 It inhibits PGD2-induced accumulation of cAMP in both washed platelets and platelet-rich plasma with IC50 values of 0.09 and 4.0 nM, respectively.1 In a sheep model of allergic rhinitis, 0.1 mg/kg MK-0524 completely blocked PGD2-induced nasal congestion.1 At a dose of 4 mg/kg, MK-0524 suppressed a nicotinic acid-induced vasodilatory response by 80% in a mouse model of flushing, an undesirable side-effect of niacin treatment for dyslipidemia.2 In an in vitro model of amyotrophic lateral sclerosis, MK-0524 has been shown to partially protect cultured motor neurons from PGD2-induced toxicity.3,4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sturino, C.F., O'Neill, G., Lachance, N., 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-tetrahydrocyclopental[b]indol-3-yl]-acetic acid. J. Med. Chem. 50(4), 794-806 (2007).

    2. Cheng, K., Wu, T.J., Wu, K.K., et al. Antagonism of the prostaglandin D2 receptor 1 suppresses nicotinic acid-induced vasodilation in mice and humans. Proc. Natl. Acad. Sci. USA 103(17), 6682-6687 (2006).

    3. Marchetto, M.C.N., Muotri, A.R., Mu, Y., et al. Non-cell-autonomous effect of human SOD1G37R astrocytes on motor neurons derived from human embryonic stem cells. Cell. Stem Cell 3(6), 649-657 (2008).

    4. Di Giorgio, F.P., Boulting, G.L., Bobrowicz, S., et al. Human embryonic stem cell-derived motor neurons are sensitive to the toxic effect of glial cells carrying an ALS-causing mutation. Cell. Stem Cell 3(6), 637-648 (2008).

    Product Citations

    Matsumoto, N., Singh, N., Lee, K.S., et al. The epoxy fatty acid pathway enhances cAMP in mammalian cells through multiple mechanisms. Prostaglandins Other Lipid Mediat. 162, 106662 (2022).