Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H32O5 |
Molecular Weight | 352.4651 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H]2C[C@H](OO2)[C@@H]1C\C=C/CCCC(O)=O
InChI
InChIKey=YIBNHAJFJUQSRA-YNNPMVKQSA-N
InChI=1S/C20H32O5/c1-2-3-6-9-15(21)12-13-17-16(18-14-19(17)25-24-18)10-7-4-5-8-11-20(22)23/h4,7,12-13,15-19,21H,2-3,5-6,8-11,14H2,1H3,(H,22,23)/b7-4-,13-12+/t15-,16+,17+,18-,19+/m0/s1
Molecular Formula | C20H32O5 |
Molecular Weight | 352.4651 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 2 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.hmdb.ca/metabolites/HMDB01381Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7248665 | https://www.ncbi.nlm.nih.gov/pubmed/2798452 | https://www.ncbi.nlm.nih.gov/pubmed/3691505 | https://www.ncbi.nlm.nih.gov/pubmed/3691505 | https://www.ncbi.nlm.nih.gov/pubmed/10903770 | https://www.ncbi.nlm.nih.gov/pubmed/11202416
Sources: http://www.hmdb.ca/metabolites/HMDB01381
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/7248665 | https://www.ncbi.nlm.nih.gov/pubmed/2798452 | https://www.ncbi.nlm.nih.gov/pubmed/3691505 | https://www.ncbi.nlm.nih.gov/pubmed/3691505 | https://www.ncbi.nlm.nih.gov/pubmed/10903770 | https://www.ncbi.nlm.nih.gov/pubmed/11202416
Prostaglandin H2 (PGH2) is a type of Prostaglandin which is derived from arachidonic acid and is a precursor for many other biologically significant molecules. Prostaglandins are synthesized from arachidonic acid by the prostaglandin-endoperoxide synthase enzymes, which are also called Cyclooxygenases. These enzymes generate a reactive intermediate PGH2 which has a reasonably long half-life (90-100 s). PGH2 is converted into the biologically active prostaglandins by prostaglandin isomerases, yielding Prostaglandin E2, D2 and F2 (PGE2, PGD2, and PGF2), or by thromboxane synthase to make Thromboxane A2 (TxA2) or by prostacyclin synthase to make Prostaglandin I2 (PGI2). Prostaglandin H2 was first isolated from incubations of arachidonic acid with ovine seminal vesicle microsomes, and was described as a potent vasoconstrictor. Thromboxane receptors can be activated by PGH2 and TxA2, as well as isoprostanes, all of which produce vasoconstriction. Activation of TP receptors by either PGH2 or TxA2 contributes to hypertension of pregnancy and to the elevation of blood pressure in some forms of experimental hypertension, particularly those that involve activation of the renin-angiotensin system.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5879 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11202416 |
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Target ID: CHEMBL4411 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10903770 |
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Target ID: CHEMBL1835 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25900452 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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Localization of platelet prostaglandin production in the platelet dense tubular system. | 1976 May |
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Arterial walls are protected against deposition of platelet thrombi by a substance (prostaglandin X) which they make from prostaglandin endoperoxides. | 1976 Nov |
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Inhibition of PGE1-stimulated cAMP accumulation in human platelets by thromboxane a2. | 1977 Apr |
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Interactions of prostaglandin H2 and thromboxane A2 with human serum albumin. | 1980 Aug |
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Influence of human low density and high density lipoprotein cholesterol on the in vitro prostaglandin I2 synthetase activity. | 1980 Dec 5 |
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Prostaglandin H2 directly lowers human platelet cAMP levels. | 1983 Jun 1 |
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[Synthesis of thromboxane A2: limiting stages of primary thrombocyte aggregation in humans initiated by arachidonic acid and its metabolic products]. | 1984 Dec |
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[Kinetic mechanisms of enzyme activity of the thromboxane synthetase system. Thromboxane synthetase of human platelets]. | 1984 Sep |
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Effect of OKY-046, a thromboxane A2 synthetase inhibitor, on arachidonate-induced platelet aggregation: possible role of "prostaglandin H2 steal" mechanism. | 1986 Nov |
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Evidence for coordinate, selective regulation of eicosanoid synthesis in platelet-derived growth factor-stimulated 3T3 fibroblasts and in HL-60 cells induced to differentiate into macrophages or neutrophils. | 1988 Dec 25 |
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Dihydropyridine agonist Bay K 8644 inhibits platelet activation by competitive antagonism of thromboxane A2-prostaglandin H2 receptor. | 1988 Mar |
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Prostaglandin H2 in human platelet activation: coactivator and substitute for thromboxane A2. | 1989 |
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Transient concentrations and agonist potency of PGH2 in platelet activation by endogenous arachidonate. | 1989 |
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Purification of the thromboxane A2/prostaglandin H2 receptor from human blood platelets. | 1989 Oct 5 |
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Pathophysiological role of thromboxane A2 and pharmacological approaches to its inhibition. | 1990 |
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Thromboxane synthase inhibitors, thromboxane receptor antagonists and dual blockers in thrombotic disorders. | 1991 Apr |
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Effects of KW-3635, a novel dibenzoxepin derivative of a selective thromboxane A2 antagonist, on human, guinea pig and rat platelets. | 1992 Jul |
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Anti-peptide antibodies against the human blood platelet thromboxane A2/prostaglandin H2 receptor. Production, purification and characterization. | 1993 May 25 |
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Tepoxalin, a novel dual inhibitor of the prostaglandin-H synthase cyclooxygenase and peroxidase activities. | 1995 Jun 9 |
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Site-directed mutagenesis of human prostacyclin synthase: Alteration of Cys441 of the Cys-pocket, and Glu347 and Arg350 of the EXXR motif. | 1996 Jul 8 |
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Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides. | 2000 Jul 21 |
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Identification of mu-class glutathione transferases M2-2 and M3-3 as cytosolic prostaglandin E synthases in the human brain. | 2000 May |
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Structural insights into the stereochemistry of the cyclooxygenase reaction. | 2000 May 4 |
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Activation of the Ah receptor signaling pathway by prostaglandins. | 2001 |
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Prostaglandin endoperoxides and thromboxane A2 activate the same receptor isoforms in human platelets. | 2002 Jan |
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Genetic variation in cyclooxygenase 1: effects on response to aspirin. | 2003 Jan |
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Thromboxane synthase (TBXAS1) polymorphisms in African-American and Caucasian populations: evidence for selective pressure. | 2005 Oct |
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Cyclooxygenase-2 and thromboxane synthase in non-endocrine and endocrine tumors: a review. | 2005 Winter |
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Thromboxane synthase mutations in an increased bone density disorder (Ghosal syndrome). | 2008 Mar |
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Expression of proliferative and inflammatory markers in a full-thickness human skin equivalent following exposure to the model sulfur mustard vesicant, 2-chloroethyl ethyl sulfide. | 2010 Dec 1 |
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LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22. | 2010 Feb 1 |
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Characterization of scavengers of gamma-ketoaldehydes that do not inhibit prostaglandin biosynthesis. | 2010 Jan |
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Structure-based discovery of inhibitors of microsomal prostaglandin E2 synthase-1, 5-lipoxygenase and 5-lipoxygenase-activating protein: promising hits for the development of new anti-inflammatory agents. | 2011 Mar 24 |
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Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase. | 2012 Jan |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7248665
Guinea-pig lung strip, dog saphenous vein strip, rabbit and rat aortic strips, guinea-pig ileum, guinea-pig fundic strip, dog and cat iris sphincter muscles and cat tracheal strips were used for activity evaluation. The preparations were suspended under a resting tension of 1 g (dog saphenous vein, guinea-pig ileum and fundus and cat trachea) or 0.5 g (guinea-pig lung strip, rat and rabbit aortae, cat and dog iris sphincter muscles) and changes in tension measured isometrically.
The preparations were superfused at a rate of 10 ml/min with modified Krebs solution at 37°C containing indomethacin (1.4 x 10^-6 mol/l), atropine (2 x 10^-7 mol/l) and phenoxybenzamine (3.5 x 10^-7 mol/l) and gassed with 5% CO2 in oxygen. PGH2, prepared by incubating arachidonic acid with ram seminal vesicle microsomes. For use, the diethyl ether was evaporated under a N2 stream and the PGH2 redissolved in Krebs solution at 0°C to give a concentration of 5 mkg/ml. Doses of PGH2 were taken as aliquots from this stock solution. Dosing was begun 15 s after addition of the Krebs solution and was always complete within a further 105 s.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 18:33:30 UTC 2023
by
admin
on
Sat Dec 16 18:33:30 UTC 2023
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Record UNII |
J670X3LRU2
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Record Status |
Validated (UNII)
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Record Version |
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PROSTAGLANDIN H2
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57405
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DTXSID80903949
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J670X3LRU2
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15554
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42935-17-1
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