Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H32O5 |
| Molecular Weight | 352.4651 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O
InChI
InChIKey=BHMBVRSPMRCCGG-OUTUXVNYSA-N
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,12-13,15-18,21-22H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,18-/m0/s1
PGD2 (Prostaglandin D2) is a major cellular regulator, has been shown to bind different receptors: D prostanoid receptor (DP) and chemoattractant receptor-homologous molecule expressed on Th2 cells (CRTH2). PGD2 reportedly inhibits platelet aggregation, the proliferation of cells, and activation of neutrophils. This compound is also a potent vasodilator that also relaxes smooth muscle but causes contraction of the bronchial airways. PGD2 promotes T cell migration via CRTH2 and aggravates asthma. In contrast, there have been some studies suggesting that PGD2 exerts anti-inflammatory effects via DP, such as inhibiting the migration and activation of neutrophils, basophils, dendritic cells and T cells. Elevated levels of prostaglandin D2 (PGD2) have been shown to be present in the bald scalp of androgenic alopecia (AGA) patients and was suggested the PGD(2)-GPR44 pathway as a potential target for treatment. Also was revealed, that PGD2 might be a new target for asthma therapy, PGD2 in serum and BALF were lower in the treated group than in the untreated group.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q9Y5Y4 Gene ID: 11251.0 Gene Symbol: PTGDR2 Target Organism: Homo sapiens (Human) |
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Target ID: Q13258 Gene ID: 5729.0 Gene Symbol: PTGDR Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Diminished platelet adenylate cyclase activation by prostaglandin D2 in acute thrombosis. | 1979 Sep |
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| Prostaglandin D2 generation after activation of rat and human mast cells with anti-IgE. | 1982 Oct |
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| Effect of prostaglandins on morphine-induced catalepsy in mice. | 1983 Sep-Dec |
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| Serum albumin enhances the impairment of platelet aggregation with thromboxane synthase inhibition by increasing the formation of prostaglandin D2. | 1984 Jul 1 |
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| Transformation of prostaglandin D2 to 9 alpha, 11 beta-(15S)-trihydroxyprosta-(5Z,13E)-dien-1-oic acid (9 alpha, 11 beta-prostaglandin F2): a unique biologically active prostaglandin produced enzymatically in vivo in humans. | 1985 Sep |
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| Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils: a potential mast cell-eosinophil interaction. | 1989 |
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| Nociceptive effects induced by intrathecal administration of prostaglandin D2, E2, or F2 alpha to conscious mice. | 1990 Feb 26 |
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| Identification of skin as a major site of prostaglandin D2 release following oral administration of niacin in humans. | 1992 May |
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| Relative contributions of direct and indirect mechanisms mediating endothelin-induced contraction of guinea-pig trachea. | 1993 Nov |
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| Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans following the application of sorbic acid. | 1994 Nov |
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| Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo. | 1995 Apr |
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| Molecular cloning and characterization of the human prostanoid DP receptor. | 1995 Aug 11 |
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| Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes. | 1997 Dec 11 |
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| Release of prostaglandin D2 by murine mast cells: importance of metabolite formation for antiproliferative activity. | 1998 |
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| Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist. | 1998 Apr |
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| Sequence, catalytic properties and expression of chicken glutathione-dependent prostaglandin D2 synthase, a novel class Sigma glutathione S-transferase. | 1998 Jul 15 |
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| A novel biological role for prostaglandin D2 is suggested by distribution studies of the rat DP prostanoid receptor. | 1999 Jul 14 |
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| Importance of the extracellular domain for prostaglandin EP(2) receptor function. | 1999 Sep |
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| Pharmacological characterization of [(3)H]-prostaglandin E(2) binding to the cloned human EP(4) prostanoid receptor. | 2000 Aug |
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| Regulation of endothelial nitric oxide synthase by PGD(2) in the developing choroid. | 2000 Jan |
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| Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans after the application of cinnamic aldehyde. | 2001 Jul |
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| Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2. | 2002 Dec |
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| Expression and molecular pharmacology of the mouse CRTH2 receptor. | 2003 Aug |
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| Deficient prostaglandin E2 production by bronchial fibroblasts of asthmatic patients, with special reference to aspirin-induced asthma. | 2003 May |
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| Chemoattractant receptor-homologous molecule expressed on Th2 cells activation in vivo increases blood leukocyte counts and its blockade abrogates 13,14-dihydro-15-keto-prostaglandin D2-induced eosinophilia in rats. | 2003 Nov |
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| PPARgamma ligands induce prostaglandin production in vascular smooth muscle cells: indomethacin acts as a peroxisome proliferator-activated receptor-gamma antagonist. | 2003 Oct |
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| GPR109A (PUMA-G/HM74A) mediates nicotinic acid-induced flushing. | 2005 Dec |
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| Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2. | 2005 Mar |
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| Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2. | 2005 Sep 16 |
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| Prostaglandin D2 mediates neuronal damage by amyloid-beta or prions which activates microglial cells. | 2006 Feb |
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| GW627368X ((N-{2-[4-(4,9-diethoxy-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl)phenyl]acetyl} benzene sulphonamide): a novel, potent and selective prostanoid EP4 receptor antagonist. | 2006 Jun |
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| Effects of laropiprant on nicotinic acid-induced flushing in patients with dyslipidemia. | 2008 Mar 1 |
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| NMDA-induced seizure intensity is enhanced in COX-2 deficient mice. | 2008 Nov |
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| Combined bezafibrate and medroxyprogesterone acetate: potential novel therapy for acute myeloid leukaemia. | 2009 Dec 7 |
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| Mitochondrial uncoupling protein 2 inhibits mast cell activation and reduces histamine content. | 2009 Nov 15 |
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| Aldo-keto reductase 1C3 expression in MCF-7 cells reveals roles in steroid hormone and prostaglandin metabolism that may explain its over-expression in breast cancer. | 2010 Feb 15 |
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| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
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| COX-2 and PPAR-γ confer cannabidiol-induced apoptosis of human lung cancer cells. | 2013 Jan |
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| Induction but not inhibition of COX-2 confers human lung cancer cell apoptosis by celecoxib. | 2013 Nov |
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| Role of cyclooxygenase-2 in exacerbation of allergen-induced airway remodeling by multiwalled carbon nanotubes. | 2013 Oct |
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| Effects of Common Pesticides on Prostaglandin D2 (PGD2) Inhibition in SC5 Mouse Sertoli Cells, Evidence of Binding at the COX-2 Active Site, and Implications for Endocrine Disruption. | 2016 Apr |
Patents
Sample Use Guides
on mice: 1 μg of the prostaglandin D2 in 200 μl of acetone or acetone alone to the central back on days 8, 10, 12, 14, 16, and 18 after depilation, with measurement of hair length performed on day 20.
Route of Administration:
Topical
Prostaglandin D2 (PGD2) inhibits hair growth, likely through the GPR44 receptor. To test the effect of PGD2 on human hair growth, it was used explanted human hair follicles maintained in culture for 7 days. There were added increasing amounts (from 0 to 10 μM) of PGD2 or vehicle to the culture medium and measured hair length. Starting at 5 μM, PGD2 significantly inhibited hair growth. At 10 μM, PGD2-treated hair was 62 ± 5% shorter than vehicle.
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C116013
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15555
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DTXSID30897162
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PROSTAGLANDIN D2
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D015230
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ACTIVE MOIETY
