| Identification | Back Directory | [Name]
DINOPROSTONE ETHANOLAMIDE | [CAS]
194935-38-1 | [Synonyms]
PGE2-EA
DINOPROSTONE ETHANOLAMIDE
PROSTAGLANDIN E2 ETHANOLAMIDE
Prostaglandin E2 Ethanolamide Exclusive
Prostaglandin E2 Ethanolamide MaxSpecStandard
Prostaglandin E2 Ethanolamide Lipid Maps MS Standard
N-(2-HYDROXYETHYL)-9-OXO-11ALPHA,15S-DIHYDROXY-PROSTA-5Z,13E-DIEN-1-AMIDE
(Z)-N-(2-hydroxyethyl)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enamide | [Molecular Formula]
C22H37NO5 | [MDL Number]
MFCD00797645 | [MOL File]
194935-38-1.mol | [Molecular Weight]
395.53 |
| Chemical Properties | Back Directory | [Boiling point ]
611.5±55.0 °C(Predicted) | [density ]
1.134±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C | [solubility ]
DMF: >100 mg/ml
DMSO: >100 mg/ml
Ethanol: >100 mg/mlPBS (pH 7.2): 12 mg/ml | [form ]
powder | [pka]
13.79±0.60(Predicted) |
| Hazard Information | Back Directory | [Description]
Prostaglandin E2 ethanolamide (PGE2-EA) is an analog of PGE2 with improved water solubility and stability. PGE2-EA is formed via COX-2 metabolism of arachidonoyl ethanolamide (AEA; ) and acts as an agonist at E prostanoid (EP) receptors 1-4 (Kis = 2.45, 0.46, 0.2, and 0.51 μM, respectively). 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). 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. Ex vivo, PGE2-EA reduces luminal damage and lymphocyte infiltration in a human mucosal explant colitis model. | [Uses]
Prostaglandin E2 Ethanolamide-d4 is the isotope labelled analogue of Prostaglandin E2 Ethanolamide, an analogue of Prostaglandin E2 (P838610). Prostaglandin E2 is most common and most biologically potent of mammalian prostaglandins. | [Definition]
ChEBI: Prostaglandin E2 ethanolamide is a prostanoid. | [References]
[1] KEVIN R KOZAK. Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides.[J]. The Journal of Biological Chemistry, 2002, 277 47: 44877-44885. DOI: 10.1074/jbc.m206788200
[2] TONG LIU. Intercellular transfer of the cellular prion protein.[J]. The Journal of Biological Chemistry, 2002, 277 49: 47671-47678. DOI: 10.1074/jbc.m207458200
[3] M. COSTABILE . Inhibition of indoleamine 2,3-dioxygenase activity by fatty acids and prostaglandins: A structure function analysis[J]. Prostaglandins, leukotrienes, and essential fatty acids, 2017, 122: Pages 7-15. DOI: 10.1016/j.plefa.2017.06.010
[4] GUANGBI LI. Protective Action of Anandamide and Its COX-2 Metabolite against l-Homocysteine-Induced NLRP3 Inflammasome Activation and Injury in Podocytes.[J]. Journal of Pharmacology and Experimental Therapeutics, 2016, 358 1: 61-70. DOI: 10.1124/jpet.116.233239
[5] LAUREN L. NICOTRA. Prostaglandin ethanolamides attenuate damage in a human explant colitis model[J]. Prostaglandins & other lipid mediators, 2013, 100: Pages 22-29. DOI: 10.1016/j.prostaglandins.2013.01.003
[6] ROBYN RICHIE-JANNETTA . Structural determinants for calcium mobilization by prostaglandin E2 and prostaglandin F2α glyceryl esters in RAW 264.7 cells and H1819 cells[J]. Prostaglandins & other lipid mediators, 2010, 92 1: Pages 19-24. DOI: 10.1016/j.prostaglandins.2010.01.003 |
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