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Details

Stereochemistry ACHIRAL
Molecular Formula C15H9BN2O3
Molecular Weight 276.055
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AN-2898

SMILES

OB1OCC2=C1C=CC(OC3=CC(C#N)=C(C=C3)C#N)=C2

InChI

InChIKey=UBMGTTRDNUKZMT-UHFFFAOYSA-N
InChI=1S/C15H9BN2O3/c17-7-10-1-2-13(5-11(10)8-18)21-14-3-4-15-12(6-14)9-20-16(15)19/h1-6,19H,9H2

HIDE SMILES / InChI

Molecular Formula C15H9BN2O3
Molecular Weight 276.055
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Anacor Pharmaceuticals (now Pfizer) was developing AN-2898, a boron-containing, small-molecule inhibitor of type 4 cyclic nucleotide phosphodiesterase (phosphodiesterase IV), as a topically applied therapy for psoriasis and atopic dermatitis. AN-2898 inhibits the release of tumore necrosis factor-alfa (TNFα), interleukin (IL)-12, and IL-23. AN-2898 also inhibits the activity of phosphodiesterase (PDE) 4 and 7. AN-2898 IC50 values for inhibition of PDE4 and PDE7 activity is 0.06 and 0.21 uM, respectively. AN-2898 is a competitive, reversible inhibitor of PDE4 with a Ki of 65 nM. AN-2898 has been studied in clinical trials for atopic dermatitis and psoriasis. The development of AN-2898 appears to have been discontinued.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
An assessment of the genetic toxicology of novel boron-containing therapeutic agents.
2013 Jun
Application of Topical Phosphodiesterase 4 Inhibitors in Mild to Moderate Atopic Dermatitis: A Systematic Review and Meta-analysis.
2019 May 1

Sample Use Guides

The Phase 2a, six-week, double-blind, bilateral trial enrolled 46 patients, randomized 1:1 to treat atopic dermatitis lesions twice daily with either 2% AN-2728 ointment and vehicle or 1% AN-2898 ointment and vehicle
Route of Administration: Topical
AN-2898 inhibited phosphodiesterase 4 (PDE4) enzyme activity (IC50 0.060 uM) and the release of multiple cytokines including TNF-α (IC50 0.16 uM) from peripheral blood mononuclear cells (hPBMCs) stimulated by lipopolysaccharide (LPS) or phytohemag- glutinin.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:55:47 GMT 2023
Edited
by admin
on Sat Dec 16 04:55:47 GMT 2023
Record UNII
6O60L94RMB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AN-2898
Common Name English
1,2-BENZENEDICARBONITRILE, 4-((1,3-DIHYDRO-1-HYDROXY-2,1-BENZOXABOROL-5-YL)OXY)-
Systematic Name English
AN2898
Code English
Code System Code Type Description
PUBCHEM
24806574
Created by admin on Sat Dec 16 04:55:47 GMT 2023 , Edited by admin on Sat Dec 16 04:55:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID70238232
Created by admin on Sat Dec 16 04:55:47 GMT 2023 , Edited by admin on Sat Dec 16 04:55:47 GMT 2023
PRIMARY
FDA UNII
6O60L94RMB
Created by admin on Sat Dec 16 04:55:47 GMT 2023 , Edited by admin on Sat Dec 16 04:55:47 GMT 2023
PRIMARY
CAS
906673-33-4
Created by admin on Sat Dec 16 04:55:47 GMT 2023 , Edited by admin on Sat Dec 16 04:55:47 GMT 2023
PRIMARY