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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
Structure of DOCEBENONE

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

HIDE SMILES / InChI

Molecular Formula C21H26O3
Molecular Weight 326.4293
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Targets

Primary TargetPharmacologyConditionPotency

PubMed

Sample Use Guides

In Vivo Use Guide
Single dose - 80 mg/kg
Route of Administration: Oral
Substance Class Chemical
Record UNII
2XRX3BD53M
Record Status Validated (UNII)
Record Version