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 |
|---|---|---|
| Cyclooxygenase-1 serves a vital hepato-protective function in chemically induced acute liver injury. | 2015-02 |
|
| Leukotriene B(4) receptors BLT1 and BLT2 are involved in interleukin-8 production in human neutrophils induced by Trichomonas vaginalis-derived secretory products. | 2012-02 |
|
| Effect of the interaction between lipoxygenase pathway and progesterone on the regulation of hydroxysteroid 11-Beta dehydrogenase 2 in cultured human term placental trophoblasts. | 2008-03 |
|
| Activation of 5-lipoxygenase and NF-kappa B in the action of acenaphthenequinone by modulation of oxidative stress. | 2008-01 |
|
| Comparative protection against liver inflammation and fibrosis by a selective cyclooxygenase-2 inhibitor and a nonredox-type 5-lipoxygenase inhibitor. | 2007-12 |
|
| FcepsilonRI- and Fcgamma receptor-mediated production of reactive oxygen species by mast cells is lipoxygenase- and cyclooxygenase-dependent and NADPH oxidase-independent. | 2007-11-15 |
|
| Lipoxygenase inhibitors induce death receptor 5/TRAIL-R2 expression and sensitize malignant tumor cells to TRAIL-induced apoptosis. | 2007-09 |
|
| Neuroprotective effects of arachidonic acid against oxidative stress on rat hippocampal slices. | 2006-11-07 |
|
| Pharmacological modulation of TNF production in macrophages. | 2004-02 |
|
| AA-861-induced Ca(2+) mobilization in Madin Darby canine kidney cells. | 1999-12-01 |
|
| Phorbol ester-induced dermal inflammation in mice: evaluation of inhibitors of 5-lipoxygenase and antagonists of leukotriene B4 receptor. | 1994-09 |
|
| Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema. | 1993-12 |
|
| Protective effect of AA-861 (5-lipoxygenase inhibitor) on experimental acute necrotizing pancreatitis in rats. | 1993-06 |
|
| Species difference of 5-lipoxygenase derived from polymorphonuclear leukocytes on sensitivity to drugs. | 1989-05 |
|
| Effect of AA-861, a selective 5-lipoxygenase inhibitor, on models of allergy in several species. | 1988-07 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:50:57 GMT 2025
by
admin
on
Mon Mar 31 17:50:57 GMT 2025
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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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| Code System | Code | Type | Description | ||
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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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