Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H34O5 |
Molecular Weight | 354.481 |
Optical Activity | ( + ) |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O
InChI
InChIKey=GMVPRGQOIOIIMI-JCPCGATGSA-N
InChI=1S/C20H34O5/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/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17+,19+/m0/s1
Molecular Formula | C20H34O5 |
Molecular Weight | 354.481 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 1 |
Optical Activity | UNSPECIFIED |
8-Epiprostaglandin E1 (8-iso-PGE1) arises by isomerization of PGE1. This isoprostane found in human semen. 8-iso-PGE1 has very low biological activity relative to PGE1. Intravenous administration of 8-iso-PGE1 decreased systemic arterial pressure slightly and increased heart rate and myocardial contractile force slightly. The magnitude of the systemic hypotensive effect of 8-iso-PGEl was equivalent to approximately 1/125 to 1/250 of that of PGE1 in dogs. On the other hand, the pulmonary hypertensive action of 8-iso-PGE1 was 5 times greater than that of PGE1. 8-iso-PGE1 is an agonist of prostanoid TP receptor. It was proposed as a prostaglandin D2 receptor antagonist for use in the treatment of androgenic alopecia.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5679176
Curator's Comment: Weeks, J.R., Sekhar, N.C., Kupiecki, F.P. in: Sparks, R.M.. (2012) Prostaglandin Abstracts: A Guide to the Literature, page 192, retrieved from: https://books.google.ru/books?id=Pv7QBQAAQBAJ
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4427 Sources: https://www.google.com/patents/EP2037967B1 |
|||
Target ID: CHEMBL2069 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10711349 |
5.4 null [pEC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5440421
Dog: Intravenous - 0.25-16 ug/kg
Intra-arterial - 2 ug/kg
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10478564
Perfusions in the isolated rabbit ear with 8-iso-prostaglandin E1 at a final concentration of 30 nM showed a slight, but not significant, increasing effect on the vasoconstrictions induced by noradrenaline or angiotensin II.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:48:59 GMT 2025
by
admin
on
Mon Mar 31 21:48:59 GMT 2025
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Record UNII |
84W5RE239W
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Record Status |
Validated (UNII)
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21003-46-3
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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