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Revision as of 14:47, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444071775 of page Prostaglandin_H2 for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 07:56, 16 September 2024 edit Azn bookworm10 (talk | contribs)Extended confirmed users1,274 editsm formatting 
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{{DISPLAYTITLE:Prostaglandin H<sub>2</sub>}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 444070236 | verifiedrevid = 464218126
⚫ |ImageFile=Prostaglandin H2 skeletal.svg
| Name = Prostaglandin H<sub>2</sub><ref name=HMDB/>
⚫ |ImageSize=
| Reference =
⚫ |IUPACName=
⚫ | ImageFile = Prostaglandin H2 skeletal.svg
|OtherNames=
⚫ | ImageSize =
⚫ |Section1= {{Chembox Identifiers
⚫ | IUPACName =
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| OtherNames = PGH<sub>2</sub>, Endoperoxide H<sub>2</sub>, Prostaglandin R<sub>2</sub>
| SystematicName =
⚫ | Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 4483
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 392800 | ChemSpiderID = 392800
| 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 | 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
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YIBNHAJFJUQSRA-YNNPMVKQSA-N | StdInChIKey = YIBNHAJFJUQSRA-YNNPMVKQSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 42935-17-1 -->
| CASNo=42935-17-1
⚫ | PubChem = 445049
| ChEBI_Ref = {{ebicite|correct|EBI}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = J670X3LRU2
⚫ | PubChem = 445049
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15554 | ChEBI = 15554
| SMILES = O=C(O)CCC/C=C\C21OO(C1)2/C=C/(O)CCCCC | SMILES = O=C(O)CCC/C=C\C21OO(C1)2/C=C/(O)CCCCC
| MeSHName=Prostaglandin+H2 | MeSHName=Prostaglandin+H2
}} }}
|Section2= {{Chembox Properties | Section2 = {{Chembox Properties
| Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub> | Formula=C<sub>20</sub>H<sub>32</sub>O<sub>5</sub>
| MolarMass=352.465 g/mol | MolarMass=352.465 g/mol
| Appearance= | Appearance=
| Density= | Density=1.129 ± 0.06 g/mL
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=490 ± 40.0 °C
| Solubility= | Solubility=0.034 g/L
}} }}
|Section3= {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
| Section4 =
| Section5 =
| Section6 =
}} }}

'''Prostaglandin H<sub>2</sub>''' ('''PGH<sub>2</sub>'''), or '''prostaglandin H2''' ('''PGH2'''), is a type of ] and a precursor for many other biologically significant molecules. It is synthesized from ] in a reaction catalyzed by a ] enzyme.<ref>{{cite journal | vauthors = van der Donk WA, Tsai AL, Kulmacz RJ | title = The cyclooxygenase reaction mechanism | journal = Biochemistry | volume = 41 | issue = 52 | pages = 15451–8 | date = December 2002 | pmid = 12501173 | doi = 10.1021/bi026938h }}</ref> The conversion from ] to prostaglandin H<sub>2</sub> is a two-step process. First, ] catalyzes the addition of two free oxygens to form the ] bridge and a peroxide functional group to form ] (PGG<sub>2</sub>).<ref>{{Cite journal|last1=Salomon|first1=Robert G.|last2=Miller|first2=Donald B.|last3=Zagorski|first3=Michael G.|last4=Coughlin|first4=Daniel J. | name-list-style = vanc |date= October 1984 |title=Prostaglandin endoperoxides. 14. Solvent-induced fragmentation of prostaglandin endoperoxides. New aldehyde products from PGH<sub>2</sub> and a novel intramolecular 1,2-hydride shift during endoperoxide fragmentation in aqueous solution|journal=Journal of the American Chemical Society |volume=106|issue=20|pages=6049–6060|doi=10.1021/ja00332a049|issn=0002-7863}}</ref> Second, ] reduces the peroxide functional group to a ], forming prostaglandin H<sub>2</sub>. Other peroxidases like ] have been observed to reduce PGG<sub>2</sub> to PGH<sub>2</sub>.<ref>{{cite journal | vauthors = Hla T, Neilson K | title = Human cyclooxygenase-2 cDNA | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 89 | issue = 16 | pages = 7384–8 | date = August 1992 | pmid = 1380156 | pmc = 49714 | doi = 10.1073/pnas.89.16.7384 | bibcode = 1992PNAS...89.7384H | doi-access = free }}</ref> PGH<sub>2</sub> is unstable at room temperature, with a half life of 90–100 seconds,<ref name=HMDB>{{Cite HMDB|author1-link=David S. Wishart|url=http://www.hmdb.ca/metabolites/HMDB0001381|title=Showing metabocard for Prostaglandin H2 (HMDB0001381)}}</ref> so it is often converted into a different prostaglandin.

]

It is acted upon by:
* ] to create ]
* ] to create ] and 12-(S)-hydroxy-5Z,8E,10E-heptadecatrienoic acid (HHT) (see ])
* ] to create ]
* ] to create ]

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 ])

Functions of prostaglandin H<sub>2</sub>:
* regulating the constriction and dilation of blood vessels
* stimulating platelet aggregation
**binds to ] on platelets' cell membranes to trigger platelet migration and adhesion to other platelets.<ref>{{cite journal | vauthors = Woodward DF, Jones RL, Narumiya S | title = International Union of Basic and Clinical Pharmacology. LXXXIII: classification of prostanoid receptors, updating 15 years of progress | journal = Pharmacological Reviews | volume = 63 | issue = 3 | pages = 471–538 | date = September 2011 | pmid = 21752876 | doi = 10.1124/pr.110.003517 | doi-access = free }}</ref>

Effects of ] on prostaglandin H<sub>2</sub>:
* Aspirin has been hypothesized to block the conversion of arachidonic acid to prostaglandin

]
{{clear }}

== References ==
{{Reflist}}

{{Prostaglandins}}
{{Prostanoidergics}}

]
]

{{biochemistry-stub}}