A primary COX product of arachidonic acid
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Prostaglandin E2

Item No. 14010

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9-oxo-11α,15S-dihydroxy-prosta-5Z,13E-dien-1-oic acid
CAS Number
363-24-6
Synonyms
  • Dinoprostone
  • PGE2
Molecular Formula
C20H32O5
Formula Weight
352.5
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): 5 mg/ml
SMILES
O=C1[C@H](C/C=C\CCCC(O)=O)[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C1
InChi Code
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
InChi Key
XEYBRNLFEZDVAW-ARSRFYASSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    PGE2 is one of the primary COX products of arachidonic acid (Item No. 90010) and one of the most widely investigated prostaglandins. Its activity influences inflammation, fertility and parturition, gastric mucosal integrity, and immune modulation.1,2,3,4 The effects of PGE2 are transduced by at least four distinct receptors designated EP1, EP2, EP3, and EP4.5 Affinity constants (Kd) of PGE2 for these receptors range from 1-10 nM depending on the receptor subtype and tissue.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Willis, A.L., and Cornelsen, M. Repeated injection of prostaglandin E2 in rat paws induces chronic swelling and a marked decrease in pain threshold. Prostaglandins 3(3), 353-357 (1973).

    2. Jackson, G.M., Sharp, H.T., and Varner, M.W. Cervical ripening before induction of labor: A randomized trial of prostaglandin E2 gel versus low-dose oxytocin. Am. J. Obstet. Gynecol. 171(4), 1092-1096 (1994).

    3. Robert, A., Schultz, J.R., Nezamis, J.E., et al. Gastric antisecretory and antiulcer properties of PGE2, 15-methyl PGE2, and 16,16-dimethyl PGE2. Intravenous, oral and intrajejunal administration. Gastroenterology 70(3), 359-370 (1976).

    4. Arvind, P., Papavassiliou, E.D., Tsioulias, G.J., et al. Prostaglandin E2 down-regulates the expression of HLA-DR antigen in human colon adenocarcinoma cell lines. Biochemistry 34(16), 5604-5609 (1995).

    5. Coleman, R.A., Smith, W.L., and Narumiya, S. International Union of Pharmacology classification of prostanoid receptors: Properties, distribution, and structure of the receptors and their subtypes. Pharmacol. Rev. 46(2), 205-229 (1994).

    Product Citations

    Yang, J., Yamashita-Kanemaru, Y., Morris, B.I., et al. Aspirin prevents metastasis by limiting platelet TXA2 suppression of T cell immunity. Nature (2025).

    Wang, Y.X., Palla, A.R., Ho, A.T.V., et al. Multiomic profiling reveals that prostaglandin E2 reverses aged muscle stem cell dysfunction, leading to increased regeneration and strength. Cell Stem Cell 32, 1154-1169 (2025).

    Wu, Z., Xiao, H., Rao, D., et al. Analytical strategy for oxylipin annotation by combining chemical derivatization-based retention index algorithm and feature tandem mass spectrometric fragmentation as a biomarker discovery tool. Anal. Chem. 95(43), 15933-15942 (2023).

    Pang, Y., Liu, X., Zhao, C., et al. LC-MS/MS-based arachidonic acid metabolomics in acute spinal cord injury reveals the upregulation of 5-LOX and COX-2 products. Free Radic. Biol. Med. 193(Pt 1), 363-372 (2022).

    Archambault, A.-S., Brassard, J., Bernatchez, É., et al. Human and mouse eosinophils differ in their ability to biosynthesize eicosanoids, docosanoids, the endocannabinoid 2-arachidonoyl-glycerol and its congeners. Cells 11(1), 141 (2022).

    Gurusamy, M., Nasseri, S., Rampa, D.R., et al. Inhibition of microsomal prostaglandin E synthase-1 ameliorates acute lung injury in mice. J. Transl. Med. 19(1), 340 (2021).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients. FASEB J. 35(6), e21666 (2021).

    Roberts, L.M., Schwarz, B., Speranza, E., et al. Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity. iScience 24(9), 103025 (2021).

    Wang, Y., Cui, L., Georgiev, P., et al. Combination of EP4 antagonist MF-766 and anti-PD-1 promotes anti-tumor efficacy by modulating both lymphocytes and myeloid cells. Oncoimmunology 10(1), 1896643 (2021).

    Hartling, I., Cremonesi, A., Osuna, E., et al. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS. Clin. Chem. Lab. Med. 59(11), 1811-1823 (2021).

    Archambault, A.-S., Zaid, Y., Rakotoarivelo, V., et al. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites. medRxiv (2020).

    Endo, S., Suganami, A., Fukushima, K., et al. 15-Keto-PGE2 acts as a biased/partial agonist to terminate PGE2-evoked signaling. The Journal of Biological Chemisty 295(38), 13338-13352 (2020).

    Brouwers, H., Jónasdóttir, H.S., Kuipers, M.E., et al. Anti-inflammatory and proresolving effects of the omega-6 polyunsaturated fatty acid adrenic acid. J. Immunol. 205(10), 2840-2849 (2020).

    Schmidleithner, L., Thabet, Y., Schönfeld, E., et al. Enzymatic activity of HPGD in Treg cells suppresses Tconv cells to maintain adipose tissue homeostasis and prevent metabolic dysfunction. Immunity 50(5), 1232-1248 (2019).

    Meriwether, D., Sulaiman, D., Volpe, C., et al. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model. J. Clin. Invest. 130, 3670-3685 (2019).

    Allain, E.P., Rouleau, M., Le, T., et al. In activation of prostaglandin E2 as a mechanism for UGT2B17-mediated adverse effects in chronic lymphocytic leukemia. Front. Oncol. 9:606, (2019).

    Saldaña, L., Bensiamar, F., Vallés, G., et al. Immunoregulatory potential of mesenchymal stem cells following activation by macrophage-derived soluble factors. Stem Cell Res. Ther. 10(1), 58 (2019).

    Dalli, J., Colas, R.A., Walker, M.E., et al. Lipid Mediator Metabolomics via LC-MS/MS Profiling and Analysis. Clinical Metabolomics 59-72 (2018).

    Sorgi, C.A., Peti, A.P.F., Petta, T., et al. Comprehensive high-resolution multiple-reaction monitoring mass spectrometry for targeted eicosanoid assays. Sci. Data 5, 180167 (2018).

    Meurer, M., Ebert, K., Schweda, K., et al. The renal vasodilatory effect of prostaglandins is ameliorated in isolated-perfused kidneys of endotoxemic mice. Pflugers Arch. 470(11), 1691-1703 (2018).

    Chen, I.-J., Hee, S.-W., Liao, C.-H., et al. Targeting the 15-keto-PGE2-PTGR2 axis modulates systemic inflammation and survival in experimental sepsis. Free Radic. Biol. Med. 115, 113-126 (2018).

    Hennebelle, M., Zhang, M., Metherel, A.H., et al. Linoleic acid participates in the response to ischemic brain injury through oxidized metabolites that regulate neurotransmission. Sci. Rep. 7(4342), (2017).

    Venerito, M., Helmke, C., Jechorek, D., et al. Leukotriene receptor expression in esophageal squamous cell cancer and non-transformed esophageal epithelium: a matched case control study. BMC Gastroenterol. 16(1), 85 (2016).

    Suganami, A., Fujino, H., Okura, I., et al. Human DP and EP2 prostanoid receptors take on distinct forms depending on the diverse binding of different ligands. FEBS J. 283(21), 3931-3940 (2016).

    Sasaki, A., Fukuda, H., Shiida, N., et al. Determination of ω-6 and ω-3 PUFA metabolites in human urine samples using UPLC/MS/MS. Anal. Bioanal. Chem. 407(6), 1625-1639 (2015).

    Otake, S., Yoshida, K., Seira, N., et al. Cellular density-dependent fown-regulation of EP4 prostanoid receptors via the up-regulation of hypoxia-inducible factor-1a in HCA-7 human colon cancer cells. Pharm. Res. Prespect. 3(1), e00083 (2014).

    Whittle, B.J., Silverstein, A.M., Mottola, D.M., et al. Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: Treprostinil is a potent DP1 and EP2 agonist. Biochem. Pharmacol. 84(1), 68-75 (2012).

    Qi, H.-Y., Daniels, M.P., Liu, Y., et al. A cytosolic phospholipase A2-initiated lipid mediator pathway induces autophagy in macrophages. J. Immunol. 187(10), 5286-5292 (2011).

    Wobst, I., Schiffmann, S., Birod, K., et al. Dimethylcelecoxib inhibits prostaglandin E2 production. Biochem. Pharmacol. 76(1), 62-69 (2008).

    George, R.J., Sturmoski, M.A., Anant, S., et al. EP4 mediates PGE2 dependent cell survival through the PI3 kinase/AKT pathway. Prostaglandins Other Lipid Mediat. 83(1-2), 112-120 (2007).

    Fujino, H., and Regan, J.W. EP4 prostanoid receptor coupling to a pertussis toxin-sensitive inhibitory G protein. Mol. Pharm. 69(1), 5-10 (2006).

    Eligini, S., Violi, F., Banfi, C., et al. Indobufen inhibits tissue factor in human monocytes through a thromboxane-mediated mechanism. Cardiovasc. Res. 69(1), 218-226 (2006).

    Zhong, H., Willard, M., and Simons, J. NS398 reduces hypoxia-inducible factor (HIF)-1a and HIF-1 activity: Multiple-level effects involving cyclooxygenase-2 dependent and independent mechanisms. Int. J. Cancer 112, 585-595 (2004).

    Woodward, D.F., Krauss, A.H.P., Chen, J., et al. Pharmacological characterization of a novel antiglaucoma agent, bimatoprost (AGN 192024). J. Pharmacol. Exp. Ther. 305(2), 772-785 (2003).

    Levy, B.D., De Sanctis, G.T., Devchand, P.R., et al. Multi-pronged inhibition of airway hyper-responsiveness and inflammation by lipoxin A4. Nat. Med. 8(9), 1018-1023 (2002).

    Rao, C.V., Desai, D., Rivenson, A., et al. Chemoprevention of colon carcinogenesis by phenylethyl-3-methylcaffeate. Cancer Res. 55(11), 2310-2315 (1995).