Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H32O5 |
| Molecular Weight | 352.4651 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI
InChIKey=XEYBRNLFEZDVAW-GKEZHNTDSA-N
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-/m1/s1
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23400687 | https://www.ncbi.nlm.nih.gov/pubmed/4403575 | https://www.ncbi.nlm.nih.gov/pubmed/15780624
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23400687 | https://www.ncbi.nlm.nih.gov/pubmed/4403575 | https://www.ncbi.nlm.nih.gov/pubmed/15780624
15-Epi-prostaglandin E2 (15R-Prostaglandin E2) is the C-15 epimer of the naturally occurring 15S-Prostaglandin E2 (15S-PGE2) isomer. 15-Epi-prostaglandin E2 is the most physiologically abundant eicosanoid, which is produced predominantly from arachidonic acid by COX and PGES, and exists at some level in nearly all cell types. Prostaglandin E2 acts on four different receptors termed EP1 through EP4 yielding an astounding array of biological effects, but this compound shows much lower potency in most biological assays; however acid catalyzed epimerization can convert this compound to the active form - 15S-Prostaglandin E2. In the in vivo assay, 15R-PGE2 showed anti-inflammatory activity, as well as in vitro inhibition of elastase release from polymorphonuclear cells. In the from polymorphonuclear cells degranulation assay, 15R-PGE2, was the most active compound in the inhibition of myeloperoxidase release.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1995 |
260.0 nM [EC50] | ||
Target ID: CHEMBL1811 |
18.0 nM [Ki] | ||
Target ID: CHEMBL2488 |
38.0 nM [Ki] | ||
Target ID: CHEMBL3710 |
5.0 nM [Ki] | ||
Target ID: CHEMBL2489 |
3.1 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
Sample Use Guides
1 mg/ear was dissolved in acetone and topically applied in the right mouse ear immediately before to phorbol 12-myristate 13-acetate administration.
Route of Administration:
Topical
The 500 μl of a human polymorphonuclear cells (PMNs) suspension (2.5 . 106 cells/ml) and 5 μl of cytochalasin B (final concentration (Fc): 100 μm) were mixed. Subsequently, 5 μl of N-formyl-methionylleucyl- phenylalanine (fMLP) was added. The mixture was incubated for 10 min at 37°C. It was centrifuged at 1900 g for 10 min at 4°C, and the supernatant was recovered as an enzymatic source. To determine the activity on the degranulation, a suspension of PMNs was preincubated for 5 min at 37°C with 5 μl of the tested compounds (15-Epi-prostaglandin E2) before the treatment with the stimulating agent.
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38873-82-4
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5283086
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T3D76GXW94
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DTXSID801017284
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admin on Sat Dec 16 09:30:53 GMT 2023 , Edited by admin on Sat Dec 16 09:30:53 GMT 2023
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SUBSTANCE RECORD
