ALPROSTADIL ISOPROPYL ESTER

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H40O5
Molecular Weight	396.5607
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of ALPROSTADIL ISOPROPYL ESTER

Structure Search

SMILES

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

InChI

InChIKey=IVJLDARWZNUIAU-WUDJJVMMSA-N

InChI=1S/C23H40O5/c1-4-5-8-11-18(24)14-15-20-19(21(25)16-22(20)26)12-9-6-7-10-13-23(27)28-17(2)3/h14-15,17-20,22,24,26H,4-13,16H2,1-3H3/b15-14+/t18-,19+,20+,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C23H40O5
Molecular Weight	396.5607
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9486272 | http://www.google.ch/patents/US6562868

Alprostadil isopropyl ester induces a considerable and rapidly appearing increased negativity of interstitial fluid pressure in skin that will enhance edema formation. It is able to inhibit contraction of fibroblast-populated collagen gels, which depends on b1-integrin function. Taken together, Alprostadil isopropyl ester can modulate e interstitial fluid volume and interstitial fluid pressure through effects on the connective tissue cells and extracellular matrix components. Alprostadil isopropyl ester was a test compound in preclinical studies of a selective EP2 and EP4 prostanoid receptor agonists for the treatment of female sexual dysfunction.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostanoid EP2 receptor 20 Target ID: CHEMBL1881 Sources: http://www.google.ch/patents/US6562868	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Female sexual dysfunction 5 Sources: http://www.google.ch/patents/US6562868	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Prostanoid EP4 receptor stimulation produces ocular hypotension by a mechanism that does not appear to involve uveoscleral outflow.	2009-07	19234340
Fluid pressure in human dermal fibroblast aggregates measured with micropipettes.	2003-11	12878487
The percutaneous penetration of prostaglandin E1 and its alkyl esters.	1999-04-19	10099159
Effect of PGE1, PGI2, and PGF2 alpha analogs on collagen gel compaction in vitro and interstitial pressure in vivo.	1998-02	9486272

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 5 ul with 0.91 or 0.3 or 0.09 mM

Route of Administration: Other

In Vitro Use Guide

ALPROSTADIL ISOPROPYL ESTER effectively inhibited human foreskin fibroblast AG 1518-mediated contraction at a concentration of 1.0 uM. The inhibition was most pronounced at early time points and could be observed already at a concentration of 10 nM.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:49:57 GMT 2025` Edited by `admin` on `Mon Mar 31 21:49:57 GMT 2025`
Record UNII	8THV3YDD6A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALPROSTADIL ISOPROPYL ESTER

Common Name

English

ALPROSTADIL IMPURITY J [EP IMPURITY]

Preferred Name

English

1-METHYLETHYL 7-((1R,2R,3R)-3-HYDROXY-2-((1E,3S)-3-HYDROXYOCT-1-ENYL)-5-OXOCYCLOPENTYL)HEPTANOATE

Systematic Name

English

PROSTAGLANDIN E1 ISOPROPYL ESTER

Common Name

English

PROST-13-EN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, 1-METHYLETHYL ESTER, (11.ALPHA.,13E,15S)-

Systematic Name

English

Code System Code Type Description

FDA UNII

8THV3YDD6A