Page last updated: 2024-12-08

prostaglandin h2

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Prostaglandin H2: A cyclic endoperoxide intermediate produced by the action of CYCLOOXYGENASE on ARACHIDONIC ACID. It is further converted by a series of specific enzymes to the series 2 prostaglandins. [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID445049
CHEMBL ID2074582
CHEBI ID15554
SCHEMBL ID12141851
MeSH IDM0086362

Synonyms (58)

Synonym
(z)-7-[(1s,2r,3r,4r)-3-[(e,3s)-3-hydroxyoct-1-enyl]-5,6-dioxabicyclo[2.2.1]heptan-2-yl]hept-5-enoic acid
gtpl1972
u46609
CHEBI:15554 ,
(5z,13e,15s)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoic acid
(5z)-7-{(1r,4s,5r,6r)-6-[(1e,3s)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]hept-5-yl}hept-5-enoic acid
9,11-epoxymethano-pgh2
(5z,9alpha,11alpha,13e,15s)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-oic acid
2,3-dioxabicyclo[2.2.1]heptane, prosta-5,13-dien-1-oic acid deriv.
prostaglandin r2
endoperoxide h2
prosta-5,13-dien-1-oic acid, 9,11-epidioxy-15-hydroxy-, (5z,9alpha,11alpha,13e,15s)- (9ci)
15-hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoic acid
9s,11r-epidioxy-15s-hydroxy-5z,13e-prostadienoic acid
LMFA03010010
(5z,13e,15s)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5z,13e)-(15s)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
prostaglandin h2
C00427
PROSTAGLANDIN-H2 ,
pgh2
42935-17-1
(15s)hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoic acid
prosta-5,13-dien-1-oic acid, 9,11-epidioxy-15-hydroxy-, (5z,9alpha,11alpha,13e,15s)-
unii-j670x3lru2
j670x3lru2 ,
pgh 2
prosta-5,13-dien-1-oicacid, 9,11-epidioxy-15-hydroxy-, (5z,9a,11a,13e,15s)-
CHEMBL2074582
gtpl4483
(5z)-7-[(1r,4s,5r,6r)-6-[(1e,3s)-3-hydroxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
(5z,13e,15s)-9alpha, 11alpha-epidioxy-15-hydroxyprosta-5,13-dienoic acid
9,11-epoxymethano pgh2
bdbm10042
YIBNHAJFJUQSRA-YNNPMVKQSA-N
SCHEMBL12141851
(5z,13e,15s)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoic acid
(5z,13e,15s)-9a,11a-epidioxy-15-hydroxyprosta-5,13-dienoic acid
(5z,9alpha,11alpha,13e,15s)-9,11-epidioxy-15-hydroxy-prosta-5,13-dien-1-oic acid
(5z,13e)-(15s)-9,11-epidioxy-15-hydroxyprosta-5,13-dienoic acid
(15s)hydroxy-9alpha,11alpha-(epoxymethano)prosta-5,13-dienoate
9s,11r-epidioxy-15s-hydroxy-5z,13e-prostadienoate
15-hydroxy-9alpha,11alpha-peroxidoprosta-5,13-dienoate
(5z,9alpha,11alpha,13e,15s)-9,11-epidioxy-15-hydroxy-prosta-5,13-dien-1-oate
(5z,13e,15s)-9a,11a-epidioxy-15-hydroxyprosta-5,13-dienoate
(5z,9a,11a,13e,15s)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-oate
(5z,13e)-(15s)-9,11-epidioxy-15-hydroxyprosta-5,13-dienoate
(5z,9a,11a,13e,15s)-9,11-epidioxy-15-hydroxyprosta-5,13-dien-1-oic acid
(5z,13e,15s)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5z,13e)-(15s)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoate
(5z,13e)-(15s)-9-alpha,11-alpha-epidioxy-15-hydroxyprosta-5,13-dienoic acid
(5z,13e)-(15s)-9alpha,11alpha-epidioxy-15-hydroxyprosta-5,13-dienoic acid
DTXSID80903949
Q416567
(z)-7-[(1r,4s,5r,6r)-6-[(e,3s)-3-hydroxyoct-1-enyl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]hept-5-enoic acid
pgh2 (prostaglandin h2), 1 mg/500 micro l
pgh2 (prostaglandin h2), 500 micro g/ml
9alpha,11alpha-epidioxy-15s-hydroxy-prosta-5z,13e-dien-1-oic acid

Research Excerpts

Overview

Prostaglandin H2 (PGH2) is a common precursor for the synthesis of five different Prostanoids. It is a product of cycloxygenase that is known as an intrinsic vasoconstricting factor in spontaneously hypertensive rats.

ExcerptReferenceRelevance
"Prostaglandin H2 (PGH2) is a common precursor for the synthesis of five different Prostanoids via specific Prostanoid Synthases. "( Comparison of PGH2 binding site in prostaglandin synthases.
Doble, M; Paragi-Vedanthi, P, 2010
)
1.8
"Prostaglandin H2 (PGH2) is a product of cycloxygenase that is known as an intrinsic vasoconstricting factor in spontaneously hypertensive rats."( Enhanced electrical activity in mesenteric arteries from salt-loaded Dahl salt-sensitive rats: actions of prostaglandin H2 on membrane channels.
Abe, I; Fujii, K; Fujishima, M; Ohya, Y; Onaka, U, 1997
)
1.23

Actions

ExcerptReferenceRelevance
"Prostaglandin H2 displays at 500 MHz a detailed 1H-NMR in which all methylene groups are non-equivalent in C6D6 solution. "( High-field 1H NMR studies of prostaglandin H2 and its decomposition pathways.
Andersen, NH; Hartzell, CJ, 1984
)
2

Bioavailability

ExcerptReferenceRelevance
"These studies support the notion that (i) products of lipid oxidation may reduce NO bioactivity without affecting endothelial NO synthase mass or catalytic activity, (ii) the mechanisms involved in the endothelial dysfunction induced by hypercholesterolaemia and oxidized lipids may differ among vascular beds, and (iii) decreased NO bioavailability does not necessarily result in systemic hypertension, but it may enhance the sensitivity to the hypertensinogenic effect of dietary salt."( Relationship between hypercholesterolaemia, endothelial dysfunction and hypertension.
Hayakawa, H; Raij, L, 1999
)
0.3
" We suggest that hyperglycemia by elevating intracellular sorbitol induces oxidative stress, which interferes with nitric oxide bioavailability and promotes PGH(2)/TXA(2) release, both of which affect regulation of vasomotor responses of arterioles."( Contribution of polyol pathway to arteriolar dysfunction in hyperglycemia. Role of oxidative stress, reduced NO, and enhanced PGH(2)/TXA(2) mediation.
Bagi, Z; Kaminski, PM; Koller, A; Racz, A; Toth, E; Toth, J; Wolin, MS, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
mouse metaboliteAny mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
prostaglandins H
oxylipinAny member of the group of bioactive lipids made by oxidation of polyunsaturated fatty acids.
olefinic compoundAny organic molecular entity that contains at least one C=C bond.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (74)

PathwayProteinsCompounds
Metabolism14961108
Metabolism of lipids500463
Fatty acid metabolism113203
Arachidonic acid metabolism3682
Synthesis of Prostaglandins (PG) and Thromboxanes (TX)1135
Metabolism of vitamins and cofactors146155
Metabolism of water-soluble vitamins and cofactors102114
Nicotinate metabolism2243
Nicotinamide salvaging1030
Biological oxidations150276
Phase I - Functionalization of compounds69175
Cytochrome P450 - arranged by substrate type30110
Eicosanoids215
COX reactions17
Arachidonic Acid Metabolism2966
Leukotriene C4 Synthesis Deficiency2966
Piroxicam Action Pathway2967
Acetylsalicylic Acid Action Pathway2967
Etodolac Action Pathway2967
Ketoprofen Action Pathway2967
Ibuprofen Action Pathway5076
Rofecoxib Action Pathway2967
Diclofenac Action Pathway2967
Sulindac Action Pathway2967
Celecoxib Action Pathway3573
Ketorolac Action Pathway2967
Suprofen Action Pathway2967
Bromfenac Action Pathway2967
Indomethacin Action Pathway3067
Mefenamic Acid Action Pathway2967
Oxaprozin Action Pathway2967
Nabumetone Action Pathway2967
Naproxen Action Pathway2967
Diflunisal Action Pathway2967
Meloxicam Action Pathway2967
Valdecoxib Action Pathway2967
Antipyrine Action Pathway2967
Antrafenine Action Pathway2967
Carprofen Action Pathway2967
Etoricoxib Action Pathway2967
Fenoprofen Action Pathway2967
Flurbiprofen Action Pathway2967
Magnesium Salicylate Action Pathway2967
Lumiracoxib Action Pathway2967
Lornoxicam Action Pathway2967
Phenylbutazone Action Pathway2967
Nepafenac Action Pathway2967
Trisalicylate-Choline Action Pathway2967
Tolmetin Action Pathway2967
Tiaprofenic Acid Action Pathway2967
Tenoxicam Action Pathway2967
Salsalate Action Pathway2967
Salicylate-Sodium Action Pathway2967
Salicylic Acid Action Pathway2967
Acetaminophen Action Pathway2967
Disease1278231
Diseases of metabolism69121
Metabolic disorders of biological oxidation enzymes647
Defective TBXAS1 causes GHDD01
Prostaglandin and Leukotriene metabolism ( Prostaglandin and Leukotriene metabolism )2223
Blood clotting and drug effects05
Metabolism of alpha-linolenic acid615
Eicosanoid metabolism via cyclooxygenases (COX)137
Prostaglandin and leukotriene metabolism in senescence619
Quercetin and Nf-kB / AP-1 induced apoptosis09
Arachidonic acid (AA, ARA) oxylipin metabolism076
Folic acid network070
Eicosanoid lipid synthesis map17
Quercetin and Nf-kB / AP-1 induced cell apoptosis09
Selenium micronutrient network095
Eicosanoid synthesis026
Spinal cord injury08
Chromosomal and microsatellite instability in colorectal cancer02
Arachidonic acid metabolism pathway011
Arachidonic acid metabolism via COX (Cyclooxygenase) pathway035

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Solute carrier organic anion transporter family member 2A1Rattus norvegicus (Norway rat)Ki0.03820.03821.41225.8000AID679001
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (2)

Assay IDTitleYearJournalArticle
AID679001TP_TRANSPORTER: inhibition of PGE2 uptake in PGT-expressing HeLa cells1996Molecular pharmacology, Oct, Volume: 50, Issue:4
Structural determinants of substrates for the prostaglandin transporter PGT.
AID1346422Human TP receptor (Prostanoid receptors)1992Japanese journal of pharmacology, Jul, Volume: 59, Issue:3
Effects of KW-3635, a novel dibenzoxepin derivative of a selective thromboxane A2 antagonist, on human, guinea pig and rat platelets.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (406)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990172 (42.36)18.7374
1990's116 (28.57)18.2507
2000's78 (19.21)29.6817
2010's36 (8.87)24.3611
2020's4 (0.99)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 32.02

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index32.02 (24.57)
Research Supply Index6.03 (2.92)
Research Growth Index4.26 (4.65)
Search Engine Demand Index47.56 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (32.02)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews34 (8.23%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other379 (91.77%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]