Leukotriene A4
{{DISPLAYTITLE:Leukotriene A4}}
{{Chembox
| Name = Leukotriene A4
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428749275
| ImageFile = Leukotriene A4.svg
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| PIN = 4-
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|Section1={{Chembox Identifiers
| IUPHAR_ligand = 5214
| Abbreviations = LTA4
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 72059-45-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7Y7MPZ6563
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| PubChem = 5280383
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444074
| SMILES = CCCCC/C=C\C/C=C\C=C\C=C\[C@H]1[C@@H](O1)CCCC(=O)O
| InChI = 1/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1
| InChIKey = UFPQIRYSPUYQHK-WAQVJNLQBZ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UFPQIRYSPUYQHK-WAQVJNLQSA-N
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| MeSHName = D017572
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 15651
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C00909
}}
|Section2={{Chembox Properties
| C = 20 | H = 30 | O =3
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|Section3={{Chembox Structure
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|Section4={{Chembox Thermochemistry
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|Section5={{Chembox Pharmacology
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|Section6={{Chembox Explosive
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|Section7={{Chembox Hazards
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|Section8={{Chembox Related
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Leukotriene A4 (LTA4) is a leukotriene, and is the precursor for the productions of leukotriene B4 (LTB4) and leukotriene C4 (LTC4).
Biosynthesis
Following the biosynthesis of eicosanoid, triggered as a result of infection or inflammation, the resulting arachidonic acid substrate is released from the cell membrane phospholipid will enter the lipooxygenase pathway to produce leukotriene A4.{{Cite journal |last1=Abu |first1=J.I. |last2=Konje |first2=J.C. |date=March 2000 |title=Leukotrienes in gynaecology: the hypothetical value of anti-leukotriene therapy in dysmenorrhoea and endometriosis |journal=Human Reproduction Update |volume=6 |issue=2 |pages=200–205 |issn=1355-4786 |pmid=10782578 |doi=10.1093/humupd/6.2.200 |doi-access=free}}{{Cite journal |last=Marx |first=J.L. |date=1982-03-12 |title=The leukotrienes in allergy and inflammation |journal=Science |volume=215 |issue=4538 |pages=1380–1383 |doi=10.1126/science.6278589 |issn=0036-8075 |pmid=6278589 |bibcode=1982Sci...215.1380M}} In this pathway, arachidonic acid is converted into 5-hydroperoxyeicosatetraenoic acid (5-HPETE) as a result of a catalytic complex consisting of the enzyme 5-lipoxygenase (5-LO) and 5-lipoxygenase-activating protein (FLAP) in the presence of ATP and calcium ions.{{r|Abu|Marx}}{{Cite journal|last=Nicolls|first=Mark R.|last2=Voelkel|first2=Norbert F.|last3=Peters-Golden|first3=Marc|last4=Rajadas|first4=Jayakumar|last5=Fridlib|first5=Marina|last6=Inayathullah|first6=Mohammed|last7=Zamanian|first7=Roham T.|last8=Rabinovitch|first8=Marlene|last9=Farkas|first9=Laszlo|date=2013-08-28|title=Blocking Macrophage Leukotriene B4 Prevents Endothelial Injury and Reverses Pulmonary Hypertension|journal=Science Translational Medicine|volume=5|issue=200|pages=200ra117|doi=10.1126/scitranslmed.3006674|issn=1946-6234|pmid=23986401|pmc=4016764}} The resulting 5-HPETE yields the unstable allylic epoxide substrate LTA4{{Cite journal |last1=Serhan |first1=C.N. |last2=Rouzer |first2=C.A. |last3=Lindgren |first3=J.A. |last4=Dahlen |first4=S.E. |last5=Samuelsson |first5=B. |date=1987-09-04 |title=Leukotrienes and lipoxins: structures, biosynthesis, and biological effects |journal=Science |volume=237 |issue=4819 |pages=1171–1176 |doi=10.1126/science.2820055 |issn=0036-8075 |pmid=2820055 |bibcode=1987Sci...237.1171S}} which is quickly hydrolyzed by the leukotriene A4 hydrolase (LTA4H) enzyme to produce LTB4, or synthesized by leukotriene C4 synthase (LTC4S) with the addition of glutathione to produce LTC4 which can be further metabolized to produce leukotriene D4 (LTD4) and leukotriene E4 (LTE4).{{Cite journal|last=Nicolls|first=Mark R.|last2=Dixon|first2=J. Brandon|last3=Kitajewski|first3=Jan|last4=Peters-Golden|first4=Marc|last5=Voelkel|first5=Norbert F.|last6=Dhillon|first6=Gundeep S.|last7=Zamanian|first7=Roham T.|last8=Feroze|first8=Abdullah H.|last9=Nepiyushchikh|first9=Zhanna|date=2017-05-10|title=Leukotriene B4 antagonism ameliorates experimental lymphedema|journal=Science Translational Medicine|volume=9|issue=389|pages=eaal3920|doi=10.1126/scitranslmed.aal3920|issn=1946-6234|pmid=28490670|doi-access=free}}{{r|Serhan}} The lipooxygenase pathway is one of several possible pathways including the cyclooxygenase pathway (also PGH synthase pathway), isoprostane pathway, and cytochrome P450 epoxygenases pathway following the arachidonic acid metabolism,{{Cite journal|last=O'Connor|first=J. Patrick|last2=Lysz|first2=Thomas|date=September 2008|title=Celecoxib, NSAIDs and the skeleton|journal=Drugs of Today|volume=44|issue=9|pages=693–709|doi=10.1358/dot.2008.44.9.1251573|issn=1699-3993|pmid=19137124}} but is the only pathway in which the subsequent steps will lead to the production of leukotrienes.
