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Prostaglandin D2 information


Prostaglandin D2
Names
IUPAC name
9α,15S-Dihydroxy-11-oxo-prosta-5Z,13E-dien-1-oic acid
Identifiers
CAS Number
  • 41598-07-6 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15555 ☒N
ChemSpider
  • 395250 ☒N
ECHA InfoCard 100.164.741 Edit this at Wikidata
IUPHAR/BPS
  • 1881
  • 1891
KEGG
  • C00696 ☒N
MeSH Prostaglandin+D2
PubChem CID
  • 448457
UNII
  • RXY07S6CZ2 checkY
CompTox Dashboard (EPA)
  • DTXSID30897162 Edit this at Wikidata
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 352.471 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Prostaglandin D2 (or PGD2) is a prostaglandin that binds to the receptor PTGDR (DP1), as well as CRTH2 (DP2).[1][2] 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[3] 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.[4] 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.[5] 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.[5]

  1. ^ Saito S, Tsuda H, Michimata T (May 2002). "Prostaglandin D2 and reproduction". American Journal of Reproductive Immunology. 47 (5): 295–302. doi:10.1034/j.1600-0897.2002.01113.x. PMID 12148545. S2CID 9284645.
  2. ^ Pettipher R, Hansel TT (2008). "Antagonists of the prostaglandin D2 receptor CRTH2". Drug News & Perspectives. 21 (6): 317–22. doi:10.1358/dnp.2008.21.6.1246831. PMID 18836589. Retrieved 9 April 2011.
  3. ^ Morrow, JD; Parsons Wg, 3rd; Roberts Lj, 2nd (August 1989). "Release of markedly increased quantities of prostaglandin D2 in vivo in humans following the administration of nicotinic acid". Prostaglandins. 38 (2): 263–74. doi:10.1016/0090-6980(89)90088-9. PMID 2475889.{{cite journal}}: CS1 maint: numeric names: authors list (link)
  4. ^ Garza, Luis A.; et al. (21 March 2012). "Prostaglandin D2 Inhibits Hair Growth and Is Elevated in Bald Scalp of Men with Androgenetic Alopecia". Science Translational Medicine. 4 (126): 126ra34. doi:10.1126/scitranslmed.3003122. ISSN 1946-6234. PMC 3319975. PMID 22440736.
  5. ^ a b Lee Phillips, Melissa (2012). "Clues to the cause of male pattern baldness". Nature. doi:10.1038/nature.2012.10277.

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Prostaglandin D2

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Prostaglandin D2 (or PGD2) is a prostaglandin that binds to the receptor PTGDR (DP1), as well as CRTH2 (DP2). It is a major prostaglandin produced by...

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Prostaglandin

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types of prostaglandin, including prostaglandin I2 (prostacyclin; PGI2), prostaglandin D2 (PGD2), prostaglandin E2 (PGE2), and prostaglandin F2α (PGF2α)...

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Prostaglandin D2 receptor

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The prostaglandin D2 (PGD2) receptors are G protein-coupled receptors that bind and are activated by prostaglandin D2. Also known as PTGDR or DP receptors...

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Prostaglandin D2 synthase

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glutathione-independent prostaglandin D synthase that catalyzes the conversion of prostaglandin H2 (PGH2) to prostaglandin D2 (PGD2). PGD2 functions as...

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Prostaglandin H2

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12-Hydroxyheptadecatrienoic acid) Prostaglandin D2 synthase to create prostaglandin D2 Prostaglandin E synthase to create prostaglandin E2 It rearranges non-enzymatically...

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Prostaglandin E2

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Prostaglandin E2 (PGE2), also known as dinoprostone, is a naturally occurring prostaglandin with oxytocic properties that is used as a medication. Dinoprostone...

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Cyclooxygenase

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Cyclooxygenase (COX), officially known as prostaglandin-endoperoxide synthase (PTGS), is an enzyme (specifically, a family of isozymes, EC 1.14.99.1)...

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Prostaglandin DP2 receptor

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Prostaglandin D2 receptor 2 (DP2 or CRTH2) is a human protein encoded by the PTGDR2 gene and GPR44. DP2 has also been designated as CD294 (cluster of differentiation...

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Aspirin

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of Surgeons in London, showed aspirin suppressed the production of prostaglandins and thromboxanes. For this discovery he was awarded the 1982 Nobel Prize...

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Prostaglandin F2alpha

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Prostaglandin F2α (PGF2α in prostanoid nomenclature), pharmaceutically termed dinoprost is a naturally occurring prostaglandin used in medicine to induce...

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Prostacyclin

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Prostacyclin (also called prostaglandin I2 or PGI2) is a prostaglandin member of the eicosanoid family of lipid molecules. It inhibits platelet activation...

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Prostaglandin DP1 receptor

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The prostaglandin D2 receptor 1 (DP1), a G protein-coupled receptor encoded by the PTGDR1 gene (also termed PTGDR), is primarily a receptor for prostaglandin...

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Paracetamol

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especially similar to selective COX-2 inhibitors. Paracetamol inhibits prostaglandin synthesis by reducing the active form of COX-1 and COX-2 enzymes. This...

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Prostaglandin E1

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Prostaglandin E1 (PGE1) is a naturally occurring prostaglandin and is also used as a medication (alprostadil). In infants with congenital heart defects...

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Arachidonic acid

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in animal fats. It is a precursor in the formation of leukotrienes, prostaglandins, and thromboxanes. Together with omega-3 fatty acids and other omega-6...

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Ketorolac

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non-selectively to block the prostaglandin synthesis by inhibition of prostaglandin G/H synthesis 1 and 2. Prostaglandin functions in the body as a messenger...

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Carprofen

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administered intravenously to horses. A single dose has been shown to reduce prostaglandin E2 production and inflammatory exudate for up to 15 hours, although...

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Misoprostol

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Misoprostol is a synthetic prostaglandin medication used to prevent and treat stomach and duodenal ulcers, induce labor, cause an abortion, and treat...

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Ketoprofen

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antipyretic effects. It acts by inhibiting the body's production of prostaglandin. It was patented in 1967 and approved for medical use in 1980. Ketoprofen...

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Indometacin

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swelling from inflammation. It works by inhibiting the production of prostaglandins, endogenous signaling molecules known to cause these symptoms. It does...

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D2

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Dopamine receptor D2, a protein Levuglandin D2 Prostaglandin D2 receptor, a G-protein coupled receptor Resolvin D2 Cyclin D2 (CCND2) Vitamin D2, or ergocalciferol...

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Dexketoprofen

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involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would...

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Thromboxane

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enzyme found in platelets, converts the arachidonic acid derivative prostaglandin H2 to thromboxane. People with asthma tend to have increased thromboxane...

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Selenium

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DP1Tooltip Prostaglandin D2 receptor 1 Agonists: Prostaglandin D2 Treprostinil Antagonists: Asapiprant Laropiprant Vidupiprant DP2Tooltip Prostaglandin D2 receptor...

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Ibuprofen

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period. Like other NSAIDs, it works by inhibiting the production of prostaglandins by decreasing the activity of the enzyme cyclooxygenase (COX). Ibuprofen...

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Latanoprost

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the eye, itchiness, and darkening of the iris. Latanoprost is in the prostaglandin analogue family of medications. It works by increasing the outflow of...

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