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

Molecular Formula	C20H32O5
Molecular Weight	352.4651
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	2
Optical Activity	UNSPECIFIED

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 1447
Prostaglandin D2 receptor 1 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 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Asthma 244 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
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.	2016-04	26359731
Identification of the major prostaglandin glycerol ester hydrolase in human cancer cells.	2014-12-05	25301951
Suppression by resveratrol of prostaglandin D2-stimulated osteoprotegerin synthesis in osteoblasts.	2014-09	24813642
Prostaglandin D2 toxicity in primary neurons is mediated through its bioactive cyclopentenone metabolites.	2013-12	23973622
Induction but not inhibition of COX-2 confers human lung cancer cell apoptosis by celecoxib.	2013-11	23943857
Role of cyclooxygenase-2 in exacerbation of allergen-induced airway remodeling by multiwalled carbon nanotubes.	2013-10	23642096
COX-2 and PPAR-γ confer cannabidiol-induced apoptosis of human lung cancer cells.	2013-01	23220503
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.	2012	23056435
Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases.	2011-10-27	21916510
Zwitterionic CRTh2 antagonists.	2011-03-24	21355602
Hematopoietic-Prostaglandin D2 synthase through PGD2 production is involved in the adult ovarian physiology.	2011-02-25	21352547
Lipopolysaccharide induces proinflammatory cytokines and chemokines in experimental otitis media through the prostaglandin D2 receptor (DP)-dependent pathway.	2011-02	21166666
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.	2010-11	20719937
A novel transporter of SLC22 family specifically transports prostaglandins and co-localizes with 15-hydroxyprostaglandin dehydrogenase in renal proximal tubules.	2010-07-16	20448048
Inhibition of soluble epoxide hydrolase enhances the anti-inflammatory effects of aspirin and 5-lipoxygenase activation protein inhibitor in a murine model.	2010-03-15	19896470
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.	2010-02-15	20036328
Combined bezafibrate and medroxyprogesterone acetate: potential novel therapy for acute myeloid leukaemia.	2009-12-07	19997560
Mitochondrial uncoupling protein 2 inhibits mast cell activation and reduces histamine content.	2009-11-15	19846869
Functional selectivity of natural and synthetic prostaglandin EP4 receptor ligands.	2009-10	19584306
Resveratrol inhibits prostaglandin formation in IL-1beta-stimulated SK-N-SH neuronal cells.	2009-09-14	19751497
Sequence, catalytic properties and expression of chicken glutathione-dependent prostaglandin D2 synthase, a novel class Sigma glutathione S-transferase.	1998-07-15	9657971
Characterization of the recombinant human prostanoid DP receptor and identification of L-644,698, a novel selective DP agonist.	1998-04	9579725
Induction of the nuclear orphan receptor RORgamma during adipocyte differentiation of D1 and 3T3-L1 cells.	1998-03	9543393
Release of prostaglandin D2 by murine mast cells: importance of metabolite formation for antiproliferative activity.	1998	9836493
Molecular cloning and characterization of the four rat prostaglandin E2 prostanoid receptor subtypes.	1997-12-11	9537820
Ligand binding specificities of the eight types and subtypes of the mouse prostanoid receptors expressed in Chinese hamster ovary cells.	1997-09	9313928
Absence of prostaglandin E2-induced hyperalgesia in NMDA receptor epsilon subunit knockout mice.	1997-04	9113374
Prostaglandins stimulate the stress-induced synthesis of hsp27 and alpha B crystallin.	1997-03	9066782
Increased urinary excretion of the prostaglandin D2 metabolite 9 alpha, 11 beta-prostaglandin F2 after aspirin challenge supports mast cell activation in aspirin-induced airway obstruction.	1996-08	8757220
Molecular cloning and characterization of the human prostanoid DP receptor.	1995-08-11	7642548
Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo.	1995-04	7712673
Release of markedly increased quantities of prostaglandin D2 from the skin in vivo in humans following the application of sorbic acid.	1994-11	7979442
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.	1994-05	8182221
Relative contributions of direct and indirect mechanisms mediating endothelin-induced contraction of guinea-pig trachea.	1993-11	7507780
Prostaglandins antagonize fibroblast proliferation stimulated by tumor necrosis factor.	1991-01-31	1993070
Nociceptive effects induced by intrathecal administration of prostaglandin D2, E2, or F2 alpha to conscious mice.	1990-02-26	2322844
Metabolism of prostaglandin D2 by human cerebral cortex into 9 alpha, 11 beta-prostaglandin F2 by an active NADPH-dependent 11-ketoreductase.	1989-07	2723663
Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils: a potential mast cell-eosinophil interaction.	1989	2526527
Transformation of prostaglandin D2 to isomeric prostaglandin F2 compounds by human eosinophils. A potential mast cell-eosinophil interaction.	1988-10-01	3139758
Release of prostaglandin D2 into human airways during acute antigen challenge.	1986-09-25	3462506
Prostaglandin D2 potentiates airway responsiveness to histamine and methacholine.	1986-02	3511806
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.	1985-11-15	3002327
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.	1985-09	3862115
Modification of dyskinesias following the intrastriatal injection of prostaglandins in the rodent.	1985-08	3862460
Cytochemical localization of adenylate cyclase in the dense tubule system of human blood platelets stimulated by forskolin, prostacyclin and prostaglandin D2.	1985-06-30	3890960
Serum albumin enhances the impairment of platelet aggregation with thromboxane synthase inhibition by increasing the formation of prostaglandin D2.	1984-07-01	6430299
Effect of prostaglandins on morphine-induced catalepsy in mice.	1983-09-01	6679984
Prostaglandin D2 generation after activation of rat and human mast cells with anti-IgE.	1982-10	6809826
Diminished platelet adenylate cyclase activation by prostaglandin D2 in acute thrombosis.	1979-09	380688
Prostaglandin d2 as a potential antithrombotic agent.	1975-01	806102

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:49:58 GMT 2025` Edited by `admin` on `Mon Mar 31 17:49:58 GMT 2025`
Record UNII	RXY07S6CZ2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

PROSTAGLANDIN D2

Common Name

English

PGD2

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C782