A selective EP4 receptor agonist
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L-902,688

Item No. 10007712

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(1E,3R)-4,4-difluoro-3-hydroxy-4-phenyl-1-buten-1-yl]-1-[6-(2H-tetrazol-5R-yl)hexyl]-2-pyrrolidinone
CAS Number
634193-54-7
Molecular Formula
C21H27F2N5O2
Formula Weight
419.5
Purity
≥98%
Formulation
A 5 mg/ml solution in methanol
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 30 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
[H]N1C(CCCCCCN2[C@@H](/C=C/[C@](O)([H])C(F)(F)C3=CC=CC=C3)CCC2=O)=NN=N1
InChi Code
InChI=1S/C21H27F2N5O2/c22-21(23,16-8-4-3-5-9-16)18(29)13-11-17-12-14-20(30)28(17)15-7-2-1-6-10-19-24-26-27-25-19/h3-5,8-9,11,13,17-18,29H,1-2,6-7,10,12,14-15H2,(H,24,25,26,27)/b13-11+/t17-,18+/m0/s1
InChi Key
WPTLQOYLIXWRNN-SLKVGHROSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $215

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    1 mg

    $409

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    5 mg

    $1,502

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    Product Description

    Prostaglandin E2 (PGE2) activates four E prostanoid (EP) receptors, EP1-4. EP4 is a Gs protein-coupled receptor that, by elevating the second messenger cAMP, plays important roles in bone formation and resorption, cancer, and atherosclerosis.1,2,3 L-902,688 is a highly potent agonist of the human PGE2 receptor, EP4. It demonstrates a Ki value of 0.38 nM and an EC50 value of 0.6 nM and is >4,000-fold selective for EP4 over other EP and prostanoid receptors.4 L-902,688 induces thermal hyperalgesia when injected into guinea pig forepaw and increases vasodilation of human pulmonary vein.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Li, M., Thompson, D.D., and Paralkar, V.M. Prostaglandin E2 receptors in bone formation. Int. Orthop. 31(6), 767-772 (2007).

    2. Hawcroft, G., Ko, C.W.S., and Hull, M.A. Prostaglandin E2-EP4 receptor signalling promotes tumorigenic behaviour of HT-29 human colorectal cancer cells. Oncogene 26(21), 3006-3019 (2007).

    3. Babaev, V.R., Chew, J.D., Ding, L., et al. Macrophage EP4 deficiency increases apoptosis and suppresses early atherosclerosis. Cell Metab. 8(6), 492-501 (2008).

    4. Young, R.N., Billot, X., Han, Y., et al. Discovery and synthesis of a potent, selective and orally bioavailable EP4 receptor agonist. Heterocycles 64(1), 437-445 (2004).

    5. Clark, P., Rowland, S.E., Denis, D., et al. MF498 [N-{[4-(5,9-diethoxy-6-oxo-6,8-dihydro-7H-pyrrolo[3,4-g]quinolin-7-yl)-3-methylbenzyl]sulfonyl}-2-(2-methoxyphenyl)acetamide], a selective E prostanoid receptor 4 antagonist, relieves joint inflammation and pain in rodent models of rheumatoid and osteoarthritis. J. Pharmacol. Exp. Ther. 325(2), 425-434 (2008).

    6. Foudi, N., Kotelevets, L., Louedec, L., et al. Vasorelaxation induced by prostaglandin E2 in human pulmonary vein: Role of the EP4 receptor subtype. Br. J. Pharmacol. 154(8), 1631-1639 (2008).

    Product Citations

    DeMars, K.M., McCrea, A.P., Siwarski, D.M., et al. Protective effects of L-902,688, a prostanoid EP4 receptor agonist, against acute blood-brain barrier damage in experimental ischemic stroke. Front. Neurosci. (2018).