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
| Molecular Formula | C20H32O4 |
| Molecular Weight | 336.4657 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 4 |
| Optical Activity | UNSPECIFIED |
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 |
|
| Conversion of leukotriene A4 to leukotriene B4: catalysis by human liver microsomes under anaerobic conditions. | 1987 Dec |
|
| 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 |
|
| Pharmacokinetics, safety, and ability to diminish leukotriene synthesis by zileuton, an inhibitor of 5-lipoxygenase. | 1991 |
|
| Relationship between leukotriene B4 and immunological parameters in rheumatoid synovial fluids. | 1991 Dec |
|
| Inhibition of 5-lipoxygenase product formation and polymorphonuclear cell degranulation by tenidap sodium in patients with rheumatoid arthritis. | 1991 Feb |
|
| Peroxisomal leukotriene degradation: biochemical and clinical implications. | 1993 |
|
| Calcium ionophore (A-23187) induced peritoneal eicosanoid biosynthesis: a rapid method to evaluate inhibitors of arachidonic acid metabolism in vivo. | 1993 |
|
| [The relationship between serum leukotriene B4 and smoking]. | 1993 Aug |
|
| Leukotriene B4 formation during human neutrophil keratinocyte interactions: evidence for transformation of leukotriene A4 by putative keratinocyte leukotriene A4 hydrolase. | 1993 Mar |
|
| Omega-hydroxylation of lipoxin B4 by human neutrophil microsomes: identification of omega-hydroxy metabolite of lipoxin B4 and catalysis by leukotriene B4 omega-hydroxylase (cytochrome P-450LTB omega). | 1993 May 20 |
|
| LTB4-induced transient neutropenia in the rat: a model for evaluating efficacy and bioavailability of LTB4 receptor antagonists. | 1993 Nov |
|
| Structure/activity relationship of leukotriene B4 and its structural analogues in chemotactic, lysosomal-enzyme release and receptor-binding assays. | 1993 Nov 15 |
|
| Levels of prostaglandin E2 and leukotriene B4 in tears of vernal conjunctivitis patients during a therapeutic trial with indomethacin. | 1994 |
|
| Intrinsic 5-lipoxygenase activity is required for neutrophil responsivity. | 1994 Aug 16 |
|
| In vivo characterization of zymosan-induced mouse peritoneal inflammation. | 1994 Jun |
|
| Eosinophil 15-lipoxygenase is a leukotriene A4 synthase. | 1994 Oct 28 |
|
| The PPARalpha-leukotriene B4 pathway to inflammation control. | 1996 Nov 7 |
|
| Enhancement of leukotriene B4 release in stimulated asthmatic neutrophils by platelet activating factor. | 1997 Dec |
|
| Effects of tepoxalin, a dual inhibitor of cyclooxygenase/5-lipoxygenase, on events associated with NSAID-induced gastrointestinal inflammation. | 1997 Jun |
|
| Fatty acids, eicosanoids, and hypolipidemic agents identified as ligands of peroxisome proliferator-activated receptors by coactivator-dependent receptor ligand assay. | 1997 Jun |
|
| Epicutaneous application of leukotriene B4 induces patterns of tenascin and a heparan sulfate proteoglycan epitope that are typical for psoriatic lesions. | 1997 May |
|
| [Content of arachidonic acid metabolites in blood and saliva of children with bronchial asthma]. | 1997 Sep-Dec |
|
| Capacity for repeatable leukotriene generation after transient stimulation of mast cells and macrophages. | 1998 Feb 1 |
|
| Leukotriene B4 mediates histamine induction of NF-kappaB and IL-8 in human bronchial epithelial cells. | 1998 Jun |
|
| The role of platelet activating factor and other lipid mediators in inflammatory angiogenesis. | 1998 May 20 |
|
| Activation of nitric oxide synthase is involved in tamoxifen-induced apoptosis of human erythroleukemia K562 cells. | 1998 Sep 4 |
|
| Leukotriene C4 is a tight-binding inhibitor of microsomal glutathione transferase-1. Effects of leukotriene pathway modifiers. | 1999 Jan 22 |
|
| LTRA inhibition of exercise-induced bronchoconstriction. | 2000 Sep 15 |
|
| Dose selection and dosing interval determination for LTRA use in asthma. | 2000 Sep 15 |
|
| Urine leukotriene B4 in familial Mediterranean fever. | 2004 Jul-Aug |
|
| Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004 Oct |
|
| Modulation of pulmonary leukotriene B4 production by cyclooxygenase-2 inhibitors and lipopolysaccharide. | 2004 Oct 15 |
|
| Leukotrienes modulate cytokine release from dendritic cells. | 2005 Dec |
|
| The anti-apoptotic effect of leukotriene B4 in neutrophils: a role for phosphatidylinositol 3-kinase, extracellular signal-regulated kinase and Mcl-1. | 2006 Apr |
|
| 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 |
|
| Oxygenation of omega-3 fatty acids by human cytochrome P450 4F3B: effect on 20-hydroxyeicosatetraenoic acid production. | 2006 Sep |
|
| Anti-inflammatory activity of a potent, selective leukotriene A4 hydrolase inhibitor in comparison with the 5-lipoxygenase inhibitor zileuton. | 2007 Jun |
|
| Chemoprevention of familial adenomatous polyposis by natural dietary compounds sulforaphane and dibenzoylmethane alone and in combination in ApcMin/+ mouse. | 2007 Oct 15 |
|
| 12(S)-Hydroxyheptadeca-5Z, 8E, 10E-trienoic acid is a natural ligand for leukotriene B4 receptor 2. | 2008 Apr 14 |
|
| RANTES (CCL5) potentiates calcium ionophore in the production of LTB4 in rat adherent macrophages from granuloma induced by KMnO4: inhibiton by NDGA. | 2008 Jan |
|
| 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 |
|
| Cytochromes P450 from family 4 are the main omega hydroxylating enzymes in humans: CYP4F3B is the prominent player in PUFA metabolism. | 2008 Nov |
|
| The antioxidant resveratrol protects against chondrocyte apoptosis via effects on mitochondrial polarization and ATP production. | 2008 Sep |
|
| Zileuton, a new efficient and safe systemic anti-acne drug. | 2009 May |
|
| 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 |
|
| Leukotriene B4 mediates gammadelta T lymphocyte migration in response to diverse stimuli. | 2010 Feb |
|
| 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 |
|
| 4-Hydroxynonenal enhances MMP-9 production in murine macrophages via 5-lipoxygenase-mediated activation of ERK and p38 MAPK. | 2010 Jan 15 |
|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:45:11 UTC 2023
by
admin
on
Fri Dec 15 17:45:11 UTC 2023
|
| Record UNII |
1HGW4DR56D
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C608
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
1HGW4DR56D
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
71160-24-2
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
LEUKOTRIENE B4
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
D007975
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
57461
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
15647
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
C609
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
5280492
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
DTXSID4037162
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | |||
|
m6777
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY | Merck Index | ||
|
DB12961
Created by
admin on Fri Dec 15 17:45:12 UTC 2023 , Edited by admin on Fri Dec 15 17:45:12 UTC 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
INHIBITOR -> TARGET |
|
