U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
The 8-isoprostaglandins: evidence for eight compounds in human semen.
1979 Feb
Quantitative determination of alprostadil (PGE) in bulk drug and pharmaceutical formulations by high-performance liquid chromatography.
1984 Jan 20
A series of prostaglandin F2-like compounds are produced in vivo in humans by a non-cyclooxygenase, free radical-catalyzed mechanism.
1990 Dec
Influence of isoprostanes on vasoconstrictor effects of noradrenaline and angiotensin II.
1999 Jul 28
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 Sat Dec 16 08:00:18 GMT 2023
Edited
by admin
on Sat Dec 16 08:00:18 GMT 2023
Record UNII
84W5RE239W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
8-ISO-PGE1
Common 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 Sat Dec 16 08:00:19 GMT 2023 , Edited by admin on Sat Dec 16 08:00:19 GMT 2023
PRIMARY
FDA UNII
84W5RE239W
Created by admin on Sat Dec 16 08:00:19 GMT 2023 , Edited by admin on Sat Dec 16 08:00:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID901185206
Created by admin on Sat Dec 16 08:00:19 GMT 2023 , Edited by admin on Sat Dec 16 08:00:19 GMT 2023
PRIMARY
CAS
21003-46-3
Created by admin on Sat Dec 16 08:00:19 GMT 2023 , Edited by admin on Sat Dec 16 08:00:19 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP