Prostaglandin D2

Prostaglandin D2

Names
IUPAC name 9α,15S-dihydroxy-11-oxo-prosta-5Z,13E-dien-1-oic acid
Identifiers
CAS Number	41598-07-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:15555 N
ChemSpider	395250 N
ECHA InfoCard	100.164.741
IUPHAR/BPS	1881 1891
KEGG	C00696 N
MeSH	Prostaglandin+D2
PubChem CID	448457
InChI 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 N Key: BHMBVRSPMRCCGG-OUTUXVNYSA-N N InChI=1/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 Key: BHMBVRSPMRCCGG-OUTUXVNYBP
SMILES CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

(or PGD₂) is a prostaglandin that binds to the receptor PTGDR (DP₁), as well as CRTH2 (DP₂). It is a major prostaglandin produced by mast cells – recruits Th2 cells, eosinophils, and basophils. In mammalian organs, large amounts of PGD₂ are found only in the brain and in mast cells. It is critical to development of allergic diseases such as asthma. Research carried out in 1989 found PGD₂ is the primary mediator of vasodilation (the "niacin flush") after ingestion of niacin (nicotinic acid).

A 2012 research paper indicates a causal link between elevated levels of localized PGD₂ and hair growth inhibition. Applied topically, the researchers found PGD₂ prevents hair growth, and mice that were genetically inclined to produce higher levels of PGD₂ had inhibited hair growth. The researchers also found PGD₂ levels were much higher in balding scalp tissue than nonbalding scalp tissue, through increased levels of prostaglandin D2 synthase. The paper suggested that inhibition of hair growth involved binding of PGD₂ to a receptor called GPR44, and that GPR44 therefore would be a therapeutic target for androgenic alopecia in both men and women with hair loss and thinning. Because PGD₂'s relation to asthma has been known for several years, several drugs that seek to reduce the effect of PGD₂ through blocking the GPR44 are already in clinical trials.

In 2012, the University of Pennsylvania published study concluding that PGD2 was found in higher levels than normal on the scalp of balding men. It seems that PGD2 prevents the hair follicles from maturing. This indicates that PGD2 inhibits hair growth in the scalp.