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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
Structure of 8-EPIPROSTAGLANDIN E1

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

HIDE SMILES / InChI

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

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

Targets

Primary TargetPharmacologyConditionPotency
5.4 null [pEC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Relationship between the chemical structure of prostaglandins and their vasoactivities in dogs.
1972 Jan
Quantitative determination of alprostadil (PGE) in bulk drug and pharmaceutical formulations by high-performance liquid chromatography.
1984 Jan 20
Patents

Sample Use Guides

Dog: Intravenous - 0.25-16 ug/kg Intra-arterial - 2 ug/kg
Route of Administration: Other
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 Mon Mar 31 21:48:59 GMT 2025
Edited
by admin
on Mon Mar 31 21:48:59 GMT 2025
Record UNII
84W5RE239W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
8-ISO-PGE1
Preferred Name English
8-EPIPROSTAGLANDIN E1
Common Name English
ALPROSTADIL IMPURITY F [EP IMPURITY]
Common Name English
PROST-13-EN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (8.BETA.,11.ALPHA.,13E,15S)-
Systematic Name English
8-ISOPROSTAGLANDIN E1, (+)-
Common Name English
11.ALPHA.,15-(S)-DIHYDROXY-9-OXO-13-TRANS-8-ISOPROSTENOIC ACID
Systematic Name English
ISOPROSTAGLANDIN E1
Common Name English
OVINONIC ACID
Common Name English
7-((1S,2R,3R)-3-HYDROXY-2-((1E,3S)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENTYL)HEPTANOIC ACID
Systematic Name English
Code System Code Type Description
PUBCHEM
5283212
Created by admin on Mon Mar 31 21:48:59 GMT 2025 , Edited by admin on Mon Mar 31 21:48:59 GMT 2025
PRIMARY
FDA UNII
84W5RE239W
Created by admin on Mon Mar 31 21:48:59 GMT 2025 , Edited by admin on Mon Mar 31 21:48:59 GMT 2025
PRIMARY
EPA CompTox
DTXSID901185206
Created by admin on Mon Mar 31 21:48:59 GMT 2025 , Edited by admin on Mon Mar 31 21:48:59 GMT 2025
PRIMARY
CAS
21003-46-3
Created by admin on Mon Mar 31 21:48:59 GMT 2025 , Edited by admin on Mon Mar 31 21:48:59 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP