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 19 Target ID: CHEMBL1881 Sources: http://www.google.ch/patents/US6562868	Agonist 2678

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

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 `Sat Dec 16 08:01:34 GMT 2023` Edited by `admin` on `Sat Dec 16 08:01:34 GMT 2023`
Record UNII	8THV3YDD6A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALPROSTADIL ISOPROPYL ESTER

Common 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

ALPROSTADIL IMPURITY J [EP IMPURITY]

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