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
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
| 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 |
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 |
|---|---|---|---|
Target ID: P01111 Gene ID: 4893.0 Gene Symbol: NRAS Target Organism: Homo sapiens (Human) |
|||
Target ID: P01112 Gene ID: 3265.0 Gene Symbol: HRAS Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A biotinylated analog of the anti-proliferative prostaglandin A1 allows assessment of PPAR-independent effects and identification of novel cellular targets for covalent modification. | 2010-01-05 |
|
| Prostaglandin A1 inhibits increases in intracellular calcium concentration, TXA(2) production and platelet activation. | 2006-05 |
|
| Ligands of the peroxisome proliferator-activated receptors (PPAR-gamma and PPAR-alpha) reduce myocardial infarct size. | 2002-07 |
|
| Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2. | 2002-06-21 |
|
| Induction of the heat-shock response by antiviral prostaglandins in human cells infected with human immunodeficiency virus type 1. | 1998-09-01 |
|
| Prostaglandins stimulate the stress-induced synthesis of hsp27 and alpha B crystallin. | 1997-03 |
|
| Inhibition of nuclear factor kappa B by prostaglandin A1: an effect associated with heat shock transcription factor activation. | 1997-01-21 |
|
| Inhibition of HIV-1 replication by cyclopentenone prostaglandins in acutely infected human cells. Evidence for a transcriptional block. | 1996-04-15 |
|
| Prostaglandins in the treatment of cancer. | 1994-04 |
|
| Prostaglandin A inhibits replication of human immunodeficiency virus during acute infection. | 1991-11 |
|
| Urinary 6-keto-prostaglandin F1a in patients with gynaecological tumours. | 1987-02 |
|
| Screening for new compounds with antiherpes activity. | 1984-10 |
|
| Prostaglandin-macromolecule interactions. I. Noncovalent binding of prostaglandins A1, E1, F2alpha, and E2 by human and bovine serum albumins. | 1976-05 |
|
| A comparison of the diuretic effects of prostaglandin A1, sodium ethacrynate, and placebo. | 1975-07 |
Patents
Sample Use Guides
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
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
Edited
Mon Mar 31 17:55:12 GMT 2025
by
admin
on
Mon Mar 31 17:55:12 GMT 2025
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| Record UNII |
VYR271N44P
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| Record Status |
Validated (UNII)
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| Record Version |
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14152-28-4
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
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