An EP receptor agonist
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Prostaglandin E2 Ethanolamide

Item No. 14012

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(2-hydroxyethyl)-9-oxo-11α,15S-dihydroxy-prosta-5Z,13E-dien-1-amide
CAS Number
194935-38-1
Synonyms
  • Dinoprostone Ethanolamide
  • PGE2-EA
  • Prostamide E2
Molecular Formula
C22H37NO5
Formula Weight
395.5
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >100 mg/mlDMSO: >100 mg/mlEthanol: >100 mg/mlPBS (pH 7.2): 12 mg/ml
SMILES
O=C1[C@H](C/C=C\CCCC(NCCO)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InChi Code
InChI=1S/C22H37NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-19,21,24-25,27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4-,13-12+/t17-,18+,19+,21+/m0/s1
InChi Key
GKKWUSPPIQURFM-IGDGGSTLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    500 µg

    $37

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    1 mg

    $69

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    5 mg

    $280

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    10 mg

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    Product Description

    Prostaglandin E2 ethanolamide (PGE2-EA) is an analog of PGE2 (Item No. 14010) with improved water solubility and stability. PGE2-EA is formed via COX-2 metabolism of arachidonoyl ethanolamide (AEA; Item No. 90050) and acts as an agonist at E prostanoid (EP) receptors 1-4 (Kis = 2.45, 0.46, 0.2, and 0.51 μM, respectively).1,2 It also inhibits indoleamine 2,3-dioxygenase-1 (IDO-1) in THP-1 cells and human monocytes (IC50s = 5.7 and 4.7 μM, respectively).3 PGE2-EA (10 μM) prevents morphological changes and F-actin rearrangement as well as reduces L-homocysteine-induced NLRP3 inflammasome formation and activation in podocytes.4 Ex vivo, PGE2-EA reduces luminal damage and lymphocyte infiltration in a human mucosal explant colitis model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kozak, K.R., Crews, B.C., Morrow, J.D., et al. Metabolism of the endocannabinoids, 2-arachidonylgycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides. The Journal of Biological Chemisty 277(47), 44877-44885 (2002).

    2. Liu, T., Li, R., Pan, T., et al. Intercellular transfer of the cellular prion protein. The Journal of Biological Chemisty 27(49), 47671-47678 (2002).

    3. Costabile, M., Bassal, N.K., Gerber, J.P., et al. Inhibition of indoleamine 2,3-dioxygenase activity by fatty acids and prostaglandins: A structure function analysis. Prostaglandins Leukot. Essent. Fatty Acids 122, 7-15 (2017).

    4. Li, G., Xia, M., Abais, J.M., et al. Protective action of anandamide and Its COX-2 metabolite against l-homocysteine-induced NLRP3 inflammasome activation and injury in podocytes. J. Pharmacol. Exp. Ther. 358(1), 61-70 (2016).

    5. Nicotra, L.L., vu, M.D., Harvey, B.S., et al. Prostaglandin ethanolamides attenuate damage in a human explant colitis model. Prostaglandins Other Lipid Mediat. 100-101, 22-29 (2013).

    Product Citations

    Richie-Jannetta, R., Nirodi, C.S., Crews, B.C., et al. Structural determinants for calcium mobilization by prostaglandin E2 and prostaglandin F2α glyceryl esters in RAW 264.7 cells and H1819 cells. Prostaglandins Other Lipid Mediat. 92(1-4), 19-24 (2010).