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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
Structure of PROSTAGLANDIN H2

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

HIDE SMILES / InChI

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

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Localization of platelet prostaglandin production in the platelet dense tubular system.
1976 May
Arterial walls are protected against deposition of platelet thrombi by a substance (prostaglandin X) which they make from prostaglandin endoperoxides.
1976 Nov
Inhibition of PGE1-stimulated cAMP accumulation in human platelets by thromboxane a2.
1977 Apr
Interactions of prostaglandin H2 and thromboxane A2 with human serum albumin.
1980 Aug
Influence of human low density and high density lipoprotein cholesterol on the in vitro prostaglandin I2 synthetase activity.
1980 Dec 5
Prostaglandin H2 directly lowers human platelet cAMP levels.
1983 Jun 1
[Synthesis of thromboxane A2: limiting stages of primary thrombocyte aggregation in humans initiated by arachidonic acid and its metabolic products].
1984 Dec
[Kinetic mechanisms of enzyme activity of the thromboxane synthetase system. Thromboxane synthetase of human platelets].
1984 Sep
Effect of OKY-046, a thromboxane A2 synthetase inhibitor, on arachidonate-induced platelet aggregation: possible role of "prostaglandin H2 steal" mechanism.
1986 Nov
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
Dihydropyridine agonist Bay K 8644 inhibits platelet activation by competitive antagonism of thromboxane A2-prostaglandin H2 receptor.
1988 Mar
Prostaglandin H2 in human platelet activation: coactivator and substitute for thromboxane A2.
1989
Transient concentrations and agonist potency of PGH2 in platelet activation by endogenous arachidonate.
1989
Purification of the thromboxane A2/prostaglandin H2 receptor from human blood platelets.
1989 Oct 5
Pathophysiological role of thromboxane A2 and pharmacological approaches to its inhibition.
1990
Thromboxane synthase inhibitors, thromboxane receptor antagonists and dual blockers in thrombotic disorders.
1991 Apr
Effects of KW-3635, a novel dibenzoxepin derivative of a selective thromboxane A2 antagonist, on human, guinea pig and rat platelets.
1992 Jul
Anti-peptide antibodies against the human blood platelet thromboxane A2/prostaglandin H2 receptor. Production, purification and characterization.
1993 May 25
Tepoxalin, a novel dual inhibitor of the prostaglandin-H synthase cyclooxygenase and peroxidase activities.
1995 Jun 9
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
Identification of CYP4F8 in human seminal vesicles as a prominent 19-hydroxylase of prostaglandin endoperoxides.
2000 Jul 21
Identification of mu-class glutathione transferases M2-2 and M3-3 as cytosolic prostaglandin E synthases in the human brain.
2000 May
Structural insights into the stereochemistry of the cyclooxygenase reaction.
2000 May 4
Activation of the Ah receptor signaling pathway by prostaglandins.
2001
Prostaglandin endoperoxides and thromboxane A2 activate the same receptor isoforms in human platelets.
2002 Jan
Genetic variation in cyclooxygenase 1: effects on response to aspirin.
2003 Jan
Thromboxane synthase (TBXAS1) polymorphisms in African-American and Caucasian populations: evidence for selective pressure.
2005 Oct
Cyclooxygenase-2 and thromboxane synthase in non-endocrine and endocrine tumors: a review.
2005 Winter
Thromboxane synthase mutations in an increased bone density disorder (Ghosal syndrome).
2008 Mar
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
LC-MS/MS analysis of epoxyalcohols and epoxides of arachidonic acid and their oxygenation by recombinant CYP4F8 and CYP4F22.
2010 Feb 1
Characterization of scavengers of gamma-ketoaldehydes that do not inhibit prostaglandin biosynthesis.
2010 Jan
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
Prevention of paraquat-induced apoptosis in human neuronal SH-SY5Y cells by lipocalin-type prostaglandin D synthase.
2012 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
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 Sat Dec 16 18:33:30 UTC 2023
Edited
by admin
on Sat Dec 16 18:33:30 UTC 2023
Record UNII
J670X3LRU2
Record Status Validated (UNII)
Record Version
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Name Type Language
PROSTAGLANDIN H2
Common Name English
Code System Code Type Description
PUBCHEM
445049
Created by admin on Sat Dec 16 18:33:30 UTC 2023 , Edited by admin on Sat Dec 16 18:33:30 UTC 2023
PRIMARY
WIKIPEDIA
PROSTAGLANDIN H2
Created by admin on Sat Dec 16 18:33:30 UTC 2023 , Edited by admin on Sat Dec 16 18:33:30 UTC 2023
PRIMARY
CHEBI
57405
Created by admin on Sat Dec 16 18:33:30 UTC 2023 , Edited by admin on Sat Dec 16 18:33:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID80903949
Created by admin on Sat Dec 16 18:33:30 UTC 2023 , Edited by admin on Sat Dec 16 18:33:30 UTC 2023
PRIMARY
FDA UNII
J670X3LRU2
Created by admin on Sat Dec 16 18:33:30 UTC 2023 , Edited by admin on Sat Dec 16 18:33:30 UTC 2023
PRIMARY
CHEBI
15554
Created by admin on Sat Dec 16 18:33:30 UTC 2023 , Edited by admin on Sat Dec 16 18:33:30 UTC 2023
PRIMARY
CAS
42935-17-1
Created by admin on Sat Dec 16 18:33:30 UTC 2023 , Edited by admin on Sat Dec 16 18:33:30 UTC 2023
PRIMARY
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