Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H32O4 |
| Molecular Weight | 336.4657 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 4 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O
InChI
InChIKey=VNYSSYRCGWBHLG-AMOLWHMGSA-N
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1
Leukotriene B4 is a pro-inflammatory mediator synthesized in myeloid cells from arachidonic acid. Leukotriene B4 induces recruitment and activation of neutrophils, monocytes and eosinophils. It also stimulates the production of a number of proinflammatory cytokines and mediators indicating an ability to augment and prolong tissue inflammation. Elevated levels of leukotriene B4 have been found in a number of inflammatory diseases and levels are related to disease activity in some of these. Leukotriene B4 has a central role in metabolic dysfunctions. By increasing MyD88 expression, leukotriene B4 enhances macrophage response to TLR/IL1 receptor agonists potentiating the sterile inflammation, a central event in metabolic disease progression. Thus, leukotriene B4 is a potential therapeutic target for the treatment of metabolic disorders. Leukotriene B4 could serve as a biomarker for evaluating bestatin efficacy in colorectal cancer.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inflammation and pain sensitivity: effects of leukotrienes D4, B4 and prostaglandin E1 in the rat paw. | 1983 Feb |
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| Conversion of leukotriene A4 to leukotriene B4: catalysis by human liver microsomes under anaerobic conditions. | 1987 Dec |
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| In vitro inhibition of leukotriene B4 formation by exogeneous 5-lipoxygenase inhibitors is associated with enhanced generation of 15-hydroxy-eicosatetraenoic acid (15-HETE) by human neutrophils. | 1988 |
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| Pharmacokinetics, safety, and ability to diminish leukotriene synthesis by zileuton, an inhibitor of 5-lipoxygenase. | 1991 |
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| Relationship between leukotriene B4 and immunological parameters in rheumatoid synovial fluids. | 1991 Dec |
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| Inhibition of 5-lipoxygenase product formation and polymorphonuclear cell degranulation by tenidap sodium in patients with rheumatoid arthritis. | 1991 Feb |
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| A specific assay for leukotriene B4 in human whole blood. | 1992 Dec |
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| Inhaled budesonide fails to inhibit the PAF-induced increase in plasma leukotriene B4 in man. | 1992 Jun |
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| Peroxisomal leukotriene degradation: biochemical and clinical implications. | 1993 |
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| Calcium ionophore (A-23187) induced peritoneal eicosanoid biosynthesis: a rapid method to evaluate inhibitors of arachidonic acid metabolism in vivo. | 1993 |
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| Leukotriene B4 formation during human neutrophil keratinocyte interactions: evidence for transformation of leukotriene A4 by putative keratinocyte leukotriene A4 hydrolase. | 1993 Mar |
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| Levels of prostaglandin E2 and leukotriene B4 in tears of vernal conjunctivitis patients during a therapeutic trial with indomethacin. | 1994 |
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| In vivo characterization of zymosan-induced mouse peritoneal inflammation. | 1994 Jun |
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| Fatty acids, eicosanoids, and hypolipidemic agents identified as ligands of peroxisome proliferator-activated receptors by coactivator-dependent receptor ligand assay. | 1997 Jun |
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| Capacity for repeatable leukotriene generation after transient stimulation of mast cells and macrophages. | 1998 Feb 1 |
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| Leukotriene B4 mediates histamine induction of NF-kappaB and IL-8 in human bronchial epithelial cells. | 1998 Jun |
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| Activation of nitric oxide synthase is involved in tamoxifen-induced apoptosis of human erythroleukemia K562 cells. | 1998 Sep 4 |
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| Leukotriene C4 is a tight-binding inhibitor of microsomal glutathione transferase-1. Effects of leukotriene pathway modifiers. | 1999 Jan 22 |
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| Role of 5-lipoxygenase products in the local accumulation of neutrophils in dermal inflammation in the rabbit. | 1999 Sep 15 |
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| Levels of leukotriene B4 and platelet activating factor in gingival crevicular fluid in renal transplant patients receiving cyclosporine A. | 2000 Jan |
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| Inhibition by troglitazone of the antigen-induced production of leukotrienes in immunoglobulin E-sensitized RBL-2H3 cells. | 2000 Jan |
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| Direct activation of capsaicin receptors by products of lipoxygenases: endogenous capsaicin-like substances. | 2000 May 23 |
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| LTRA inhibition of exercise-induced bronchoconstriction. | 2000 Sep 15 |
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| Dose selection and dosing interval determination for LTRA use in asthma. | 2000 Sep 15 |
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| Modulation of haem oxygenase-1 expression by nitric oxide and leukotrienes in zymosan-activated macrophages. | 2001 Jul |
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| Vitamin E suppresses 5-lipoxygenase-mediated oxidative stress in peripheral blood mononuclear cells of hemodialysis patients regardless of administration route. | 2001 May |
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| Cytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. | 2002 Jul 12 |
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| Leukotrienes mediate murine bronchopulmonary hyperreactivity, inflammation, and part of mucosal metaplasia and tissue injury induced by recombinant murine interleukin-13. | 2003 Apr |
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| Leukotrienes, IL-13, and chemokines cooperate to induce BHR and mucus in allergic mouse lungs. | 2003 Feb |
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| In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG). | 2004 Aug |
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| 5-oxo-6,8,11,14-eicosatetraenoic acid stimulates the release of the eosinophil survival factor granulocyte/macrophage colony-stimulating factor from monocytes. | 2004 Jul 2 |
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| Urine leukotriene B4 in familial Mediterranean fever. | 2004 Jul-Aug |
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| Modulation of pulmonary leukotriene B4 production by cyclooxygenase-2 inhibitors and lipopolysaccharide. | 2004 Oct 15 |
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| Leukotrienes modulate cytokine release from dendritic cells. | 2005 Dec |
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| The anti-apoptotic effect of leukotriene B4 in neutrophils: a role for phosphatidylinositol 3-kinase, extracellular signal-regulated kinase and Mcl-1. | 2006 Apr |
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| Crystal structure of anti-configuration of indomethacin and leukotriene B4 12-hydroxydehydrogenase/15-oxo-prostaglandin 13-reductase complex reveals the structural basis of broad spectrum indomethacin efficacy. | 2006 Sep |
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| Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production. | 2006 Sep |
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| Anti-inflammatory activity of a potent, selective leukotriene A4 hydrolase inhibitor in comparison with the 5-lipoxygenase inhibitor zileuton. | 2007 Jun |
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| Chemoprevention of familial adenomatous polyposis by natural dietary compounds sulforaphane and dibenzoylmethane alone and in combination in ApcMin/+ mouse. | 2007 Oct 15 |
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| 12(S)-Hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2. | 2008 Apr 14 |
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| RANTES (CCL5) potentiates calcium ionophore in the production of LTB4 in rat adherent macrophages from granuloma induced by KMnO4: inhibiton by NDGA. | 2008 Jan |
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| Effect of the interaction between lipoxygenase pathway and progesterone on the regulation of hydroxysteroid 11-Beta dehydrogenase 2 in cultured human term placental trophoblasts. | 2008 Mar |
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| Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism. | 2008 Nov |
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| The antioxidant resveratrol protects against chondrocyte apoptosis via effects on mitochondrial polarization and ATP production. | 2008 Sep |
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| Zileuton, a new efficient and safe systemic anti-acne drug. | 2009 May |
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| 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 |
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| Leukotriene B4 mediates gammadelta T lymphocyte migration in response to diverse stimuli. | 2010 Feb |
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| Connective tissue mast cells are the target of formaldehyde to induce tracheal hyperresponsiveness in rats: putative role of leukotriene B4 and nitric oxide. | 2010 Feb 1 |
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| 4-Hydroxynonenal enhances MMP-9 production in murine macrophages via 5-lipoxygenase-mediated activation of ERK and p38 MAPK. | 2010 Jan 15 |
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| Isoliquiritigenin induces growth inhibition and apoptosis through downregulating arachidonic acid metabolic network and the deactivation of PI3K/Akt in human breast cancer. | 2013 Oct 1 |
Patents
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NCI_THESAURUS |
C608
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1HGW4DR56D
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71160-24-2
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LEUKOTRIENE B4
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D007975
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57461
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15647
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C609
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5280492
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DTXSID4037162
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m6777
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DB12961
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SUBSTANCE RECORD
