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Details

Stereochemistry ACHIRAL
Molecular Formula C17H20O3
Molecular Weight 272.3389
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BUNAPROLAST

SMILES

CCCCC1=C(OC(C)=O)C2=C(C=CC=C2)C(OC)=C1

InChI

InChIKey=XKKGMVDIONCFKP-UHFFFAOYSA-N
InChI=1S/C17H20O3/c1-4-5-8-13-11-16(19-3)14-9-6-7-10-15(14)17(13)20-12(2)18/h6-7,9-11H,4-5,8H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C17H20O3
Molecular Weight 272.3389
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Bunaprolast has been described as the most potent antioxidant inhibitor of endothelial activation of NF-kB and gene expression of E-selectin and vascular cell adhesion molecule-1. Bunaprolast is a potent inhibitor of leukotriene B4 production in human whole blood and undergoes deacetylation to an initial metabolite with similar pharmacological potency. The in vivo demonstration of inhibition of pulmonary bronchoconstriction by this compound, in a model known to be leukotriene sensitive, coupled with its potent in vitro inhibition of 5-lipoxygenase enzymes, suggests bunaprolast may be of use in 5-lypoxygenase-mediated models of asthma.

Approval Year

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Rhesus monkey data
10 and 5 mg/kg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:21:17 GMT 2023
Edited
by admin
on Fri Dec 15 16:21:17 GMT 2023
Record UNII
WKF2F316K6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BUNAPROLAST
INN   USAN  
INN   USAN  
Official Name English
2-Butyl-4-methoxy-1-naphthol acetate
Systematic Name English
bunaprolast [INN]
Common Name English
BUNAPROLAST [USAN]
Common Name English
1-NAPHTHALENOL, 2-BUTYL-4-METHOXY-, ACETATE
Systematic Name English
U-66858
Code English
Classification Tree Code System Code
NCI_THESAURUS C29712
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
NCI_THESAURUS C1322
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
Code System Code Type Description
INN
6361
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
FDA UNII
WKF2F316K6
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL164349
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
NCI_THESAURUS
C74136
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
PUBCHEM
68730
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
USAN
AA-60
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
CAS
99107-52-5
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
EVMPD
SUB05976MIG
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
SMS_ID
100000088463
Created by admin on Fri Dec 15 16:21:17 GMT 2023 , Edited by admin on Fri Dec 15 16:21:17 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY