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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H36O5
Molecular Weight 356.4968
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROPROSTAGLANDIN E1

SMILES

CCCCC[C@H](O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O

InChI

InChIKey=DPOINJQWXDTOSF-DODZYUBVSA-N
InChI=1S/C20H36O5/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/h15-17,19,21,23H,2-14H2,1H3,(H,24,25)/t15-,16+,17+,19+/m0/s1

HIDE SMILES / InChI

Molecular Formula C20H36O5
Molecular Weight 356.4968
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

13,14-dihydro-prostaglandin E1 (dihydroprostaglandin E1 or 13,14-dihydro-PGE) is a biologically active metabolite of prostaglandin E1. It inhibits adenosine triphosphate (ATP) release and thromboxane generation by human platelets. Besides, the reduced influx of LDL cholesterol into the rabbit aorta after in vivo treatment with 13,14-dihydro-PGE1 is of special interest, since LDL cholesterol accumulation in the arterial wall is considered a key event in atherogenesis.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
A comparative study of the effects of iloprost and PGE1 on pulmonary arterial pressure and edema formation in the isolated perfused rat lung model.
1996 Mar
Pharmacological characterization of [(3)H]-prostaglandin E(2) binding to the cloned human EP(4) prostanoid receptor.
2000 Aug

Sample Use Guides

animals: donor animals and/or receiver animals were treated daily for 1 week with 13,14-dihydro-PGE1 (DIHYDROPROSTAGLANDIN E1), PGE1, 15-keto-PGE1, 15-keto-13,14-dihydro-PGE1, or the vehicle only, respectively. From the group of the receiver animals, a subgroup of 6 animals each was treated for the same period of time with either 13,14-dihydro-PGE1, PGE1, 15-keto-PGE1, 15-keto-13,14-dihydro-PGE1, or the vehicle. Immediately after the last administration of the respective PG or solvent, native blood from a donor rabbit was circulated [30 mL/min. under in vivo flow conditions (60 Hz)] over an arterial segment of a receiver animal.
Route of Administration: Unknown
In Vitro Use Guide
The actions of the in vivo metabolite of PGE1, 13,14-dihydro-PGE1 (DIHYDROPROSTAGLANDIN E1/ PGE0), on platelet and neutrophil (PMN) function and vessel tone were studied in vitro. PGE0 inhibited aggregation, ATP release and thromboxane generation by human platelets (IC50 10-100 nmol/l). The compound also inhibited superoxide anion generation and lysosomal enzyme release from human PMN. PGE0 was also potent relaxants of several arterial preparations in the rabbit at comparable concentrations.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:01:20 GMT 2023
Edited
by admin
on Sat Dec 16 11:01:20 GMT 2023
Record UNII
C1R6440YGW
Record Status Validated (UNII)
Record Version
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Name Type Language
DIHYDROPROSTAGLANDIN E1
Common Name English
11,15-DIHYDROXY-9-KETOPROSTANOIC ACID
Systematic Name English
13,14-DIHYDROPROSTAGLANDIN E1
Common Name English
PROSTAGLANDIN E0
Common Name English
(15S)-DIHYDROPROSTAGLANDIN E1
Common Name English
PROSTAN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, (11.ALPHA.,15S)-
Systematic Name English
11.ALPHA.,15-DIHYDROXY-9-OXOPROSTANOIC ACID
Systematic Name English
PGE0
Common Name English
U-23307
Code English
13,14-DIHYDRO-PGE1
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID401317965
Created by admin on Sat Dec 16 11:01:20 GMT 2023 , Edited by admin on Sat Dec 16 11:01:20 GMT 2023
PRIMARY
FDA UNII
C1R6440YGW
Created by admin on Sat Dec 16 11:01:20 GMT 2023 , Edited by admin on Sat Dec 16 11:01:20 GMT 2023
PRIMARY
PUBCHEM
161273
Created by admin on Sat Dec 16 11:01:20 GMT 2023 , Edited by admin on Sat Dec 16 11:01:20 GMT 2023
PRIMARY
CAS
19313-28-1
Created by admin on Sat Dec 16 11:01:20 GMT 2023 , Edited by admin on Sat Dec 16 11:01:20 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
MAJOR
PLASMA