PROSTAGLANDIN D2

Investigational

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22440736 | https://www.ncbi.nlm.nih.gov/pubmed/28669561 | https://www.ncbi.nlm.nih.gov/pubmed/28623133

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin D2 receptor 2 3 Target ID: Q9Y5Y4 Gene ID: 11251.0 Gene Symbol: PTGDR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28623133	Activator 1430
Prostaglandin D2 receptor 2 Target ID: Q13258 Gene ID: 5729.0 Gene Symbol: PTGDR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12494276	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28669561	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Androgenic alopecia 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28941500	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Suppression of immune complex vasculitis in rats by prostaglandin.	1979 Nov	159314
Effect of prostaglandins on morphine-induced catalepsy in mice.	1983 Sep-Dec	6679984
Serum albumin enhances the impairment of platelet aggregation with thromboxane synthase inhibition by increasing the formation of prostaglandin D2.	1984 Jul 1	6430299
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	3002327
Release of prostaglandin D2 into human airways during acute antigen challenge.	1986 Sep 25	3462506
Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils. A potential mast cell-eosinophil interaction.	1988 Oct 1	3139758
Metabolism of prostaglandin D2 by human cerebral cortex into 9 alpha, 11 beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase.	1989 Jul	2723663
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	8182221
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.	1997 Sep	9313928
Release of prostaglandin D2 by murine mast cells: importance of metabolite formation for antiproliferative activity.	1998	9836493
15-Deoxy-Delta(12,14)-prostaglandin J(2) facilitates thyroglobulin production by cultured human thyrocytes.	2000 Dec	11078701
A protective role for cyclooxygenase-2 in drug-induced liver injury in mice.	2001 Dec	11743745
Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2.	2002 Dec	12466225
Identification by site-directed mutagenesis of amino acids contributing to ligand-binding specificity or signal transduction properties of the human FP prostanoid receptor.	2003 Apr 15	12519077
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.	2003 Mar	12632255
Deficient prostaglandin E2 production by bronchial fibroblasts of asthmatic patients, with special reference to aspirin-induced asthma.	2003 May	12743569
PPARgamma ligands induce prostaglandin production in vascular smooth muscle cells: indomethacin acts as a peroxisome proliferator-activated receptor-gamma antagonist.	2003 Oct	12897060
GPR109A (PUMA-G/HM74A) mediates nicotinic acid-induced flushing.	2005 Dec	16322797
Structural determinants of arylacetic acid nonsteroidal anti-inflammatory drugs necessary for binding and activation of the prostaglandin D2 receptor CRTH2.	2005 Mar	15563582
Functional selectivity of natural and synthetic prostaglandin EP4 receptor ligands.	2009 Oct	19584306
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	19896470
The D prostanoid receptor agonist BW245C [(4S)-(3-[(3R,S)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxo)-4-imidazolidineheptanoic acid] inhibits fibroblast proliferation and bleomycin-induced lung fibrosis in mice.	2010 Nov	20719937
Prostaglandin D2 toxicity in primary neurons is mediated through its bioactive cyclopentenone metabolites.	2013 Dec	23973622
Induction but not inhibition of COX-2 confers human lung cancer cell apoptosis by celecoxib.	2013 Nov	23943857
Identification of the major prostaglandin glycerol ester hydrolase in human cancer cells.	2014 Dec 5	25301951

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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.

Name

Type

Language

PROSTAGLANDIN D2

Common Name

English

9,15- DIHYDROXY-11-OXO-PROSTA-5,13-DIEN-1-OIC ACID, (5Z,9-.ALPHA.,13E,15S)

Common Name

English

PGD2

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C782