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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 of PROSTAGLANDIN A1

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

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

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A comparison of the diuretic effects of prostaglandin A1, sodium ethacrynate, and placebo.
1975 Jul
Urinary 6-keto-prostaglandin F1a in patients with gynaecological tumours.
1987 Feb
Prostaglandin A inhibits replication of human immunodeficiency virus during acute infection.
1991 Nov
Prostaglandins in the treatment of cancer.
1994 Apr
Inhibition of HIV-1 replication by cyclopentenone prostaglandins in acutely infected human cells. Evidence for a transcriptional block.
1996 Apr 15
Prostaglandins stimulate the stress-induced synthesis of hsp27 and alpha B crystallin.
1997 Mar
Induction of the heat-shock response by antiviral prostaglandins in human cells infected with human immunodeficiency virus type 1.
1998 Sep 1
Effects of peroxisome proliferator-activated receptor agonists on LPS-induced neuronal death in mixed cortical neurons: associated with iNOS and COX-2.
2002 Jun 21
Prostaglandin A1 inhibits increases in intracellular calcium concentration, TXA(2) production and platelet activation.
2006 May
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
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
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 GMT 2023
Edited
by admin
on Fri Dec 15 15:21:44 GMT 2023
Record UNII
VYR271N44P
Record Status Validated (UNII)
Record Version
  • Download
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
Created by admin on Fri Dec 15 15:21:44 GMT 2023 , Edited by admin on Fri Dec 15 15:21:44 GMT 2023
PRIMARY
CAS
14152-28-4
Created by admin on Fri Dec 15 15:21:44 GMT 2023 , Edited by admin on Fri Dec 15 15:21:44 GMT 2023
PRIMARY
CHEBI
15545
Created by admin on Fri Dec 15 15:21:44 GMT 2023 , Edited by admin on Fri Dec 15 15:21:44 GMT 2023
PRIMARY
RS_ITEM_NUM
1578500
Created by admin on Fri Dec 15 15:21:44 GMT 2023 , Edited by admin on Fri Dec 15 15:21:44 GMT 2023
PRIMARY
MESH
C100573
Created by admin on Fri Dec 15 15:21:44 GMT 2023 , Edited by admin on Fri Dec 15 15:21:44 GMT 2023
PRIMARY
PUBCHEM
5281912
Created by admin on Fri Dec 15 15:21:44 GMT 2023 , Edited by admin on Fri Dec 15 15:21:44 GMT 2023
PRIMARY
FDA UNII
VYR271N44P
Created by admin on Fri Dec 15 15:21:44 GMT 2023 , Edited by admin on Fri Dec 15 15:21:44 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY