PROSTAGLANDIN A1

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H32O4
Molecular Weight	336.4657
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=BGKHCLZFGPIKKU-LDDQNKHRSA-N

InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18+/m0/s1

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27468687 | https://www.ncbi.nlm.nih.gov/pubmed/15781063 | https://www.ncbi.nlm.nih.gov/pubmed/9764807

The cyclopentenone prostaglandin A1 (PGA1) is considered as an antitumor agent. Its action basis on two distinct mechanisms: direct cytostatic/cytotoxic effects on cancer cells. In addition, the second one is the inhibitory activity of a tumor-associated enzymatic function (i.e., telomerase) that is responsible for cancer cell immortality. In addition, was shown, that PGA1 triggers apoptosis by a process that entails the specific activation of H- and N-Ras isoforms, leading to caspase activation. Rodent models with focal cerebral ischemia have shown that PGA1 has the neuroprotective potential.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GTPase NRas 1 Target ID: P01111 Gene ID: 4893.0 Gene Symbol: NRAS Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27468687	Activator 1430
GTPase HRas 2 Target ID: P01112 Gene ID: 3265.0 Gene Symbol: HRAS Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27468687	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Ischemia 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15781063	Preventing		Preclinical	Unknown Approved Use Unknown
Melanoma 88 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9764807	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Prostaglandin-macromolecule interactions. I. Noncovalent binding of prostaglandins A1, E1, F2alpha, and E2 by human and bovine serum albumins.	1976 May	944773
Induction of the heat-shock response by antiviral prostaglandins in human cells infected with human immunodeficiency virus type 1.	1998 Sep 1	9760172

Patents

Sample Use Guides

In Vivo Use Guide

in mice: 33 nmol reduced infarction volume by about 43% when administered intracerebroventricularly before and after transient ischemia in mice. in rats: PGA1 16.5-66 nmol diminished infarction volume by 18% to 27% when administered immediately following permanent ischemia in rats

Route of Administration: Other

In Vitro Use Guide

Four human melanoma cell lines were treated with graded concentrations (4-16microg/ml) of prostaglandin A1 (PGA1) for 24 or 48 h in vitro. At the end of the treatment, cell proliferation (measured in terms of DNA synthesis) and telomerase activity were determined. The results showed that PGA1 induced concentration-dependent inhibition of DNA synthesis at 48 h but not at 24 h in SK-MEL-28 cells.

Name

Type

Language

PROSTAGLANDIN A1

Common Name

English

PGA1

Common Name

English

9-OXO-15S-HYDROXY-PROSTA-10,13E-DIEN-1-OIC ACID

Common Name

English

PROSTAGLANDIN A1 [USP-RS]

Common Name

English

ALPROSTADIL IMPURITY A [EP IMPURITY]

Common Name

English

Code System Code Type Description

CHEBI

57398