U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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

PubMed

TitleDatePubMed
Species difference of 5-lipoxygenase derived from polymorphonuclear leukocytes on sensitivity to drugs.
1989 May
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema.
1993 Dec
Phorbol ester-induced dermal inflammation in mice: evaluation of inhibitors of 5-lipoxygenase and antagonists of leukotriene B4 receptor.
1994 Sep
Pharmacological modulation of TNF production in macrophages.
2004 Feb
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
Activation of 5-lipoxygenase and NF-kappa B in the action of acenaphthenequinone by modulation of oxidative stress.
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
Cyclooxygenase-1 serves a vital hepato-protective function in chemically induced acute liver injury.
2015 Feb

Sample Use Guides

Single dose - 80 mg/kg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:45 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:45 GMT 2023
Record UNII
2XRX3BD53M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOCEBENONE
INN   MART.   USAN  
USAN   INN  
Official Name English
A-61589
Code English
AA-861
Code English
DOCEBENONE [MART.]
Common Name English
2-(12-HYDROXY-5,10-DODECADIYNYL)-3,5,6-TRIMETHYL-P-BENZOQUINONE
Systematic Name English
2,5-CYCLOHEXADIENE-1,4-DIONE, 2-(12-HYDROXY-5,10-DODECADIYN-1-YL)-3,5,6-TRIMETHYL-
Systematic Name English
docebenone [INN]
Common Name English
DOCEBENONE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1322
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
Code System Code Type Description
MESH
C036837
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
INN
6442
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID0045125
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
SMS_ID
100000081845
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
FDA UNII
2XRX3BD53M
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
CHEBI
2340
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
USAN
AA-79
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
PUBCHEM
1967
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
NCI_THESAURUS
C76761
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
ChEMBL
CHEMBL304818
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
CAS
80809-81-0
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
EVMPD
SUB06345MIG
Created by admin on Fri Dec 15 15:13:45 GMT 2023 , Edited by admin on Fri Dec 15 15:13:45 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY