Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H28O3 |
| Molecular Weight | 316.4345 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 3 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC\C=C\C=C1/[C@@H](C\C=C/CCCC(O)=O)C=CC1=O
InChI
InChIKey=VHRUMKCAEVRUBK-GODQJPCRSA-N
InChI=1S/C20H28O3/c1-2-3-4-5-6-10-13-18-17(15-16-19(18)21)12-9-7-8-11-14-20(22)23/h6-7,9-10,13,15-17H,2-5,8,11-12,14H2,1H3,(H,22,23)/b9-7-,10-6+,18-13+/t17-/m0/s1
| Molecular Formula | C20H28O3 |
| Molecular Weight | 316.4345 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 3 |
| Optical Activity | UNSPECIFIED |
15-deoxy-Δ12,14-Prostaglandin J2 (15d-PGJ2) is a cyclopentanone prostaglandin and the agonist of endogenous PPAR gamma ligand, that is formed via the elimination of two molecules of water of prostaglandin D2. 15d-PGJ2 possesses anti-inflammatory effects. Experiments with animal models revealed, that 15d-PGJ2 may represent a potential therapeutic strategy in rheumatoid arthritis. Besides, 15d-PGJ2, given either systemically or locally in mice can control ongoing asthma pathological abnormalities, including eosinophil and neutrophil infiltration, mucus exacerbation, and lung remodeling triggered by ovalbumin. It was suggested, that potential exists to exploit 15d-PGJ2 as a therapeutic agent in asthma. It is known, the determination of individual prostaglandins, including 15d-PGJ2 in urine samples could improve the understanding of particular prostaglandins species under various physiological and pathological conditions. Recently was suggested the sensitive method for determination of 15d-PGJ2 and its application in human plasma samples of patients with diabetes.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Unknown Approved UseUnknown |
|||
| Palliative | Unknown Approved UseUnknown |
|||
| Diagnostic | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A prostaglandin J2 metabolite binds peroxisome proliferator-activated receptor gamma and promotes adipocyte differentiation. | 1995 Dec 1 |
|
| Inhibition of nuclear factor kappa B by prostaglandin A1: an effect associated with heat shock transcription factor activation. | 1997 Jan 21 |
|
| Unique ability of troglitazone to up-regulate peroxisome proliferator-activated receptor-gamma expression in hepatocytes. | 2002 Jan |
|
| Cyclooxygenase-2 expression by nonsteroidal anti-inflammatory drugs in human airway smooth muscle cells: role of peroxisome proliferator-activated receptors. | 2003 Jan 15 |
|
| 15-deoxy-delta 12,14-prostaglandin J2 and laminar fluid shear stress stabilize c-IAP1 in vascular endothelial cells. | 2003 Jul |
|
| Peroxisome proliferator-activated receptor ligands affect growth-related gene expression in human leukemic cells. | 2003 Jun |
|
| 15-deoxy prostaglandin J2 enhances allyl alcohol-induced toxicity in rat hepatocytes. | 2004 Feb |
|
| Differential regulation of chemokine expression by peroxisome proliferator-activated receptor gamma agonists: interactions with glucocorticoids and beta2-agonists. | 2005 Jan 28 |
|
| The selective cyclooxygenase-2 inhibitor SC-236 reduces liver fibrosis by mechanisms involving non-parenchymal cell apoptosis and PPARgamma activation. | 2005 Jul |
|
| Cardiomyocytic apoptosis following global cardiac ischemia and reperfusion can be attenuated by peroxisome proliferator-activated receptor alpha but not gamma activators. | 2006 Sep |
|
| Peroxisome proliferated-activated receptor gamma ligand, Pioglitazone, does not prevent hepatic fibrosis in mice. | 2007 Jan |
|
| Ajulemic acid, a synthetic cannabinoid acid, induces an antiinflammatory profile of eicosanoids in human synovial cells. | 2008 Nov 7 |
|
| Tanshinone IIA attenuates atherosclerosis in ApoE(-/-) mice through down-regulation of scavenger receptor expression. | 2011 Jan 10 |
Patents
Sample Use Guides
Arthritic mice: were treated with 15-deoxy Δ12,14-prostaglandin J2 (15d-PGJ2) (1 mg/kg) by the s.c. route daily for 7 days
Route of Administration:
Other
To assess the influence of 15-deoxy-Δ12,14-Prostaglandin J2 (15d-PGJ2) treatment on T cell proliferation, popliteal and inguinal lymph nodes cells harvested from arthritic mice were removed and washed twice with PBS. Tissues were minced, and the cells were filtered through a cell strainer, centrifuged at 500 ×g at 4°C for 10 min, and resuspended in RPMI-1640 medium at 2.5 × 106 cells/mL. In some wells, cells were incubated with 15d-PGJ2 (5 μM) or vehicle (DMSO 0.5%) 1 hour before stimulation. The immunosuppressive effect of 15d-PGJ2 on the inflammatory immune response during collagen-induced arthritis was revealed.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:59:45 UTC 2023
by
admin
on
Sat Dec 16 07:59:45 UTC 2023
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| Record UNII |
ALI977775J
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET -> AGONIST |
Binding Assay
IC50
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