A potent, selective agonist for the CRTH2/DP2 receptor
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15(R)-15-methyl Prostaglandin D2

Item No. 12720

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9α,15R-dihydroxy-11-oxo-15-methyl-prosta-5Z,13E-dien-1-oic acid
CAS Number
210978-26-0
Synonyms
  • 15(R)-15-methyl PGD2
Molecular Formula
C21H34O5
Formula Weight
366.5
Purity
≥95%
Formulation
A 1 mg/ml solution in methyl acetate
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >50 mg/mlEthanol: >75 mg/mlPBS (pH 7.2): >5 mg/ml
SMILES
CCCCC[C@@](C)(O)\C=C\[C@H]1C(=O)CC(O)C1C/C=C\CCCC(=O)O
InChi Code
InChI=1S/C21H34O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-18,22,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,21-/m1/s1
InChi Key
CTXLUMAOXBULOZ-BKVRKCTKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    15(R)-15-methyl Prostaglandin D2 (15(R)-15-methyl PGD2) is a metabolically stable synthetic analog of PGD2 (Item No. 12010). The physiological actions of PGD2 include regulation of sleep, lowering of body temperature, inhibition of platelet aggregation and relaxation of vascular smooth muscle.1,2,3 PGD2 mediates its effects by 2 distinct G-protein-coupled receptors, DP1and CRTH2/DP2.4,5,6 15(R)-15-methyl PGD2 is a potent, selective agonist for the CRTH2/DP2 receptor.7 The EC50 values for eosinophil CD11b expression, actin polymerization, and chemotaxis are 1.4, 3.8, and 1.7 nM, respectively, each of which is approximately 3-5 fold lower than those for PGD2. In contrast the EC50 for the DP1-mediated increase in platelet cAMP by 15(R)-15-methyl PGD2 is >10 µM.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hayaishi, O. Sleep-wake regulation by prostaglandins D2 and E2. The Journal of Biological Chemisty 263(29), 14593-14596 (1988).

    2. Onoe, H., Ueno, R., Fujita, I., et al. Prostaglandin D2, a cerebral sleep-inducing substance in monkeys. Proc. Natl. Acad. Sci. USA 85(11), 4082-4086 (1988).

    3. Giles, H., and Leff, P. The biology and pharmacology of PGD2. Prostaglandins 35(2), 277-300 (1988).

    4. Boie, Y., Sawyer, N., Slipetz, D.M., et al. Molecular cloning and characterization of the human prostanoid DP receptor. The Journal of Biological Chemisty 270(32), 18910-18916 (1995).

    5. Monneret, G., Gravel, S., Diamond, M., et al. Prostaglandin D2 is a potent chemoattractant for human eosinophils that acts via a novel DP receptor. Blood 98(6), 1942-1948 (2001).

    6. Hirai, H., Tanaka, K., Yoshie, O., et al. Prostaglandin D2 selectivity induces chemotaxis in T helper type 2 cells, eosinophils, and basophils via seven-transmembrane receptor CRTH2. J. Exp. Med. 193(2), 255-261 (2001).

    7. Monneret, G., Cossette, C., Gravel, S., et al. 15R-methyl-prostaglandin D2 is a potent and selective CRTH2/DP2 receptor agonist in human eosinophils. J. Pharmacol. Exp. Ther. 304(1), 349-355 (2003).