PGH2

プロスタグランジンH2

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2017/12/14 20:14:16」(JST)

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Prostaglandin H2

Names
Other names PGH2, Endoperoxide H2, Prostaglandin R2
Identifiers
CAS Number	42935-17-1 N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:15554 Y
ChemSpider	392800 Y
IUPHAR/BPS	4483
MeSH	Prostaglandin+H2
PubChem CID	445049
InChI 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 Y Key: YIBNHAJFJUQSRA-YNNPMVKQSA-N Y InChI=1/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 Key: YIBNHAJFJUQSRA-YNNPMVKQBN
SMILES O=C(O)CCC/C=C\C[C@H]2[C@H]1OO[C@H](C1)[C@@H]2/C=C/[C@@H](O)CCCCC
Properties
Chemical formula	C20H32O5
Molar mass	352.465 g/mol
Density	1.129 ± 40.0 g/mL
Boiling point	490 ± 40.0 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Prostaglandin H2 is a type of prostaglandin and a precursor for many other biologically significant molecules. It is synthesized from arachidonic acid in a reaction catalyzed by a cyclooxygenase enzyme.

Eicosanoid synthesis - prostaglandin H2 near center

It is acted upon by:

• Prostacyclin synthase to create prostacyclin
• Thromboxane-A synthase to create thromboxane A2 and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see 12-Hydroxyheptadecatrienoic acid)
• Prostaglandin D2 synthase to create prostaglandin D2
• Prostaglandin E synthase to create prostaglandin E2

It rearranges non-enzymatically to:

• A mixture of 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) and 12-(S)-hydroxy-5Z,8Z,10E-heptadecatrienoic acid (see 12-Hydroxyheptadecatrienoic acid)

Use of Prostaglandin H2:

• regulating the constriction and dilation of blood vessels
• stimulating platelet aggregation

Effects of Aspirin on Prostaglandin H2:

• Aspirin has been hypothesized to block the conversion of arachidonic acid to Prostaglandin

Figure 1: Synthetic pathways from PGH₂ (the parent compound) to prostaglandins, prostacyclin and thromboxanes

References

2. "Prostaglandin H2". SciFinder. Retrieved 22 October 2017.

3. "Acetylation of Prostaglandin H2 Synthases by Aspirin is Inhibited by Redox Cycling of the Peroxidase". "Biochem Pharmacol. Retrieved 22 October 2017.

UpToDate Contents

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• 1. アスピリン：リウマチ性疾患における作用機序、主な毒性、および使用aspirin mechanism of action major toxicities and use in rheumatic diseases [show details]
  …especially as it pertains to aspirin and other salicylates, and is discussed in further detail elsewhere. PGH2 synthase is a bifunctional enzyme with two adjacent but spatially distinct active sites for peroxidase …
• 2. 非ステロイド性抗炎症剤（NSAIDs）（アスピリンを含む）：胃十二指腸障害の病因nsaids including aspirin pathogenesis of gastroduodenal toxicity [show details]
  …(derived from phospholipids in cell membranes) into PGG2 and then to PGH2 The gastric and duodenal mucosa proceed to convert PGH2 to various prostanoids (prostaglandins and thromboxane A2). PGs such as…

English Journal

• Determining cyclooxygenase-2 activity in three different test systems utilizing online-solid phase extraction-liquid chromatography-mass spectrometry for parallel quantification of prostaglandin E2, D2 and thromboxane B2.

• Willenberg I1, Meschede AK2, Schebb NH3.
• Journal of chromatography. A.J Chromatogr A.2015 Apr 24;1391:40-8. doi: 10.1016/j.chroma.2015.02.059. Epub 2015 Feb 24.
• Cyclooxygenase-2 (COX-2) catalyzes the formation of PGH2 from arachidonic acid. PGH2 is further converted to different prostaglandins (PG), such as PGE2, PGD2 and TxB2. In this study a rapid online-SPE-LC-MS method for the simultaneous quantification of PGE2, PGD2 and TxB2 streamlined for COX-2 enzy
• PMID 25777050

• Cox-2 Is involved in vascular oxidative stress and endothelial dysfunction of renal interlobar arteries from obese zucker rats.

• Muñoz M1, Sánchez A1, Pilar Martínez M2, Benedito S1, López-Oliva E1, García-Sacristán A1, Hernández M1, Prieto D1.
• Free radical biology & medicine.Free Radic Biol Med.2015 Apr 1. pii: S0891-5849(15)00148-3. doi: 10.1016/j.freeradbiomed.2015.03.024. [Epub ahead of print]
• Obesity is related to vascular dysfunction through inflammation and oxidative stress and it has been identified as a risk factor for chronic renal disease. In the present study, we assessed the specific relationships between reactive oxygen species (ROS), cyclooxygenase 2 (COX-2) and endothelial dys
• PMID 25841778

• The TRPA1 channel mediates the analgesic action of dipyrone and pyrazolone derivatives.

• Nassini R1, Fusi C, Materazzi S, Coppi E, Tuccinardi T, Marone IM, De Logu F, Preti D, Tonello R, Chiarugi A, Patacchini R, Geppetti P, Benemei S.
• British journal of pharmacology.Br J Pharmacol.2015 Mar 13. doi: 10.1111/bph.13129. [Epub ahead of print]
• BACKGROUND AND PURPOSE: Although still used by hundreds of millions of people worldwide, the mechanism of the analgesic action of the pyrazolone derivatives (PDs), dipyrone, propyphenazone and antipyrine, remains unknown. The transient receptor potential ankyrin 1 (TRPA1) channel, expressed by nocic
• PMID 25765567

Japanese Journal

• 大腸化学発がんへのプロスタグランジン最終合成酵素の関与

• 日本毒性学会学術年会 39.1(0), O-45, 2012
• NAID 130005008673

• 新たなNSAIDsの標的としてのプロスタグランジン最終合成酵素

• 昭和大学薬学雑誌 2(2), 115-126, 2011-12
• NAID 120005537007

• 脊髄におけるプロスタグランジン (特集 神経研究の最近の知見--基礎と臨床から)

• 四国医学雑誌 61(1・2), 25-30, 2005-04-25
• NAID 40006794080

Related Pictures

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★リンクテーブル★

リンク元	「prostaglandin H2」
拡張検索	「PGH2シンターゼ」
関連記事	「PG」

「prostaglandin H2」

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プロスタグランジンH2

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PGH2

「PGH2シンターゼ」

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PGH2 synthase

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PGH2 synthase

「PG」

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• プロスタグランジン prostaglandin
• 大動脈弁最大圧較差

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プロスタグランジン