Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H26O3 |
Molecular Weight | 326.4293 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(C)C(=O)C(CCCCC#CCCCC#CCO)=C(C)C1=O
InChI
InChIKey=WDEABJKSGGRCQA-UHFFFAOYSA-N
InChI=1S/C21H26O3/c1-16-17(2)21(24)19(18(3)20(16)23)14-12-10-8-6-4-5-7-9-11-13-15-22/h22H,5,7-10,12,14-15H2,1-3H3
Molecular Formula | C21H26O3 |
Molecular Weight | 326.4293 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Docebenone (AA-861) is a potent, selective and orally active 5-LO (5-lipoxygenase) inhibitor. T. vaginalis-derived secretory products (TvSP)-induced IL-8 production was efficiently inhibited when trichomonads were pretreated with docebenone. Docebenone increased [Ca(2+)](i) in Madin Darby canine kidney cells by releasing Ca(2+) from multiple internal stores in a manner independent of the formation of inositol-1,4,5-trisphosphate, followed by Ca(2+) entry from external medium. In animal model, it was shown that docebenone may prove useful in the treatment of acute pancreatitis. Docebenone showed a dose-dependent inhibition of slow reacting substance of anaphylaxis (SRS-A) release, with no effect on histamine release from passively sensitized guinea pig, monkey (M. irus) and human lung fragments. It markedly suppresses biosynthesis of the leukotrienes. This drug inhibits the release of histamine as well as SRS-A from lung fragments of anaphylactic monkey (M. mulatta) and in the Ca ionophore-stimulated rat peritoneal cavity. AA-861 suppressed the anaphylactically-induced airway resistance in mepyramine- and cimetidine-treated guinea pigs. These results suggest that AA-861 may be clinically effective for treating allergy-related asthma by modulating the 5-lipoxygenase pathway and that an inhibitory mechanism of histamine release by AA-861 may be present in some species. Docebenone has shown anti-inflammatory effects in several animal models following local dosing: phorbol ester-induced oedema and neutrophil influx in mouse skin, arachidonate-induced plasma extravasation in rabbit skin, the pleural reversed passive Arthus reaction in rats.
Approval Year
PubMed
Title | Date | PubMed |
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Species difference of 5-lipoxygenase derived from polymorphonuclear leukocytes on sensitivity to drugs. | 1989 May |
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Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema. | 1993 Dec |
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Phorbol ester-induced dermal inflammation in mice: evaluation of inhibitors of 5-lipoxygenase and antagonists of leukotriene B4 receptor. | 1994 Sep |
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Pharmacological modulation of TNF production in macrophages. | 2004 Feb |
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FcepsilonRI- and Fcgamma receptor-mediated production of reactive oxygen species by mast cells is lipoxygenase- and cyclooxygenase-dependent and NADPH oxidase-independent. | 2007 Nov 15 |
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Activation of 5-lipoxygenase and NF-kappa B in the action of acenaphthenequinone by modulation of oxidative stress. | 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 |
|
Cyclooxygenase-1 serves a vital hepato-protective function in chemically induced acute liver injury. | 2015 Feb |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:13:45 GMT 2023
by
admin
on
Fri Dec 15 15:13:45 GMT 2023
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Record UNII |
2XRX3BD53M
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1322
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C036837
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6442
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DTXSID0045125
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100000081845
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2XRX3BD53M
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2340
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AA-79
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1967
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C76761
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CHEMBL304818
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80809-81-0
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SUB06345MIG
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Related Record | Type | Details | ||
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ACTIVE MOIETY |