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

HIDE SMILES / InChI

Molecular Formula	C20H32O4
Molecular Weight	336.4657
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

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
A comparison of the diuretic effects of prostaglandin A1, sodium ethacrynate, and placebo.	1975 Jul	1165130
Prostaglandin-macromolecule interactions. I. Noncovalent binding of prostaglandins A1, E1, F2alpha, and E2 by human and bovine serum albumins.	1976 May	944773
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
Urinary 6-keto-prostaglandin F1a in patients with gynaecological tumours.	1987 Feb	3545443
Prostaglandins in the treatment of cancer.	1994 Apr	8049495
Inhibition of HIV-1 replication by cyclopentenone prostaglandins in acutely infected human cells. Evidence for a transcriptional block.	1996 Apr 15	8621762
Inhibition of nuclear factor kappa B by prostaglandin A1: an effect associated with heat shock transcription factor activation.	1997 Jan 21	9012856
Prostaglandins stimulate the stress-induced synthesis of hsp27 and alpha B crystallin.	1997 Mar	9066782
Induction of the heat-shock response by antiviral prostaglandins in human cells infected with human immunodeficiency virus type 1.	1998 Sep 1	9760172
Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size.	2002 Jul	12087064
A biotinylated analog of the anti-proliferative prostaglandin A1 allows assessment of PPAR-independent effects and identification of novel cellular targets for covalent modification.	2010 Jan 5	19800325

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:21:44 UTC 2023` Edited by `admin` on `Fri Dec 15 15:21:44 UTC 2023`
Record UNII	VYR271N44P
Record Status	`Validated (UNII)`
Record Version

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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