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 |
|---|---|---|
| Suppression of immune complex vasculitis in rats by prostaglandin. | 1979 Nov |
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| 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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| 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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| Modification of dyskinesias following the intrastriatal injection of prostaglandins in the rodent. | 1985 Aug |
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| Cytochemical localization of adenylate cyclase in the dense tubule system of human blood platelets stimulated by forskolin, prostacyclin and prostaglandin D2. | 1985 Jun 30 |
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| Inhibition of platelet-activating-factor-induced human platelet activation by prostaglandin D2. Differential sensitivity of platelet transduction processes and functional responses to inhibition by cyclic AMP. | 1985 Nov 15 |
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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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| Prostaglandin D2 potentiates airway responsiveness to histamine and methacholine. | 1986 Feb |
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| Release of prostaglandin D2 into human airways during acute antigen challenge. | 1986 Sep 25 |
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| Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils. A potential mast cell-eosinophil interaction. | 1988 Oct 1 |
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| Metabolism of prostaglandin D2 by human cerebral cortex into 9 alpha, 11 beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase. | 1989 Jul |
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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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| Prostaglandins antagonize fibroblast proliferation stimulated by tumor necrosis factor. | 1991 Jan 31 |
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| Detection of the major urinary metabolite of prostaglandin D2 in the circulation: demonstration of elevated levels in patients with disorders of systemic mast cell activation. | 1994 May |
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| Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes. | 1997 Dec 11 |
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| Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells. | 1997 Sep |
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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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| Induction of the nuclear orphan receptor RORgamma during adipocyte differentiation of D1 and 3T3-L1 cells. | 1998 Mar |
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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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| 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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| 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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| On the mechanism of interaction of potent surmountable and insurmountable antagonists with the prostaglandin D2 receptor CRTH2. | 2006 Apr |
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| Combined bezafibrate and medroxyprogesterone acetate: potential novel therapy for acute myeloid leukaemia. | 2009 Dec 7 |
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| Inhibition of soluble epoxide hydrolase enhances the anti-inflammatory effects of aspirin and 5-lipoxygenase activation protein inhibitor in a murine model. | 2010 Mar 15 |
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| Lipopolysaccharide induces proinflammatory cytokines and chemokines in experimental otitis media through the prostaglandin D2 receptor (DP)-dependent pathway. | 2011 Feb |
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| Zwitterionic CRTh2 antagonists. | 2011 Mar 24 |
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| Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases. | 2011 Oct 27 |
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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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PROSTAGLANDIN D2
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D015230
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ACTIVE MOIETY
