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 UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of 15-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-CHCORRSHSA-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-/m1/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

15-Epiprostaglandin E1 is a synthetic prostaglandin analogue. The activity of the racemic synthetic prostaglandin is approximately one-half that of the naturally occurring compound. 15-Epiprostaglandin E1 is 4% and 6% as potent as PGE1 in contracting the rat uterus and guinea pig ileum. PGA1 is very potent vasodilator and hypotensive agent, whereas its epimer 15-Epiprostaglandin E1 has a little vasodilator or hypotensive effects in anaesthetized dogs. 15-Epiprostaglandin E1 is a non-competitive inhibitor of 15-hydroxyprostaglandin dehydrogenase from human placenta.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
189.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Biological activity of synthetic prostaglandins.
1969 Mar 29
Relationship between the chemical structure of prostaglandins and their vasoactivities in dogs.
1972 Jan
Kinetic studies on a 15-hydroxyprostaglandin dehydrogenase from human placenta.
1976 Nov
Conformational analysis of prastaglandins. III. Study on active sites and conformation-action relationship.
1977 Dec
Quantitative determination of alprostadil (PGE) in bulk drug and pharmaceutical formulations by high-performance liquid chromatography.
1984 Jan 20
Patents

Patents

Sample Use Guides

Unknown
Route of Administration: Intra-arterial
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 07:55:07 GMT 2023
Edited
by admin
on Sat Dec 16 07:55:07 GMT 2023
Record UNII
V2N896SN9V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
15-EPIPROSTAGLANDIN E1
Common Name English
ALPROSTADIL IMPURITY D [EP IMPURITY]
Common Name English
15-EPI-PGE1
Common Name English
PROST-13-EN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (11.ALPHA.,13E,15R)-
Systematic Name English
7-((1R,2R,3R)-3-HYDROXY-2-((1E,3R)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENTYL)HEPTANOIC ACID
Systematic Name English
15(R)-PGE1
Common Name English
Code System Code Type Description
PUBCHEM
5283056
Created by admin on Sat Dec 16 07:55:07 GMT 2023 , Edited by admin on Sat Dec 16 07:55:07 GMT 2023
PRIMARY
CAS
20897-91-0
Created by admin on Sat Dec 16 07:55:07 GMT 2023 , Edited by admin on Sat Dec 16 07:55:07 GMT 2023
PRIMARY
FDA UNII
V2N896SN9V
Created by admin on Sat Dec 16 07:55:07 GMT 2023 , Edited by admin on Sat Dec 16 07:55:07 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP