crisaborole   

GtoPdb Ligand ID: 9151

Synonyms: AN 2728 | AN2728 | compound 5b [PMID: 19303290] | Eucrisa® | Staquis®
crisaborole is an approved drug (FDA (2016), EMA (2020))
Compound class: Synthetic organic
Comment: Crisaborole is a non-steroidal phosphodiesterase-4 (PDE4) inhibitor acting primarily against the PDE4B isozyme [1]. It was developed by Anacor Pharmaceuticals for its potential anti-inflammatory action in skin conditions such as psoriasis and atopic dermatitis.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 62.48
Molecular weight 251.08
XLogP 2.46
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES N#Cc1ccc(cc1)Oc1ccc2c(c1)COB2O
Isomeric SMILES N#Cc1ccc(cc1)Oc1ccc2c(c1)COB2O
InChI InChI=1S/C14H10BNO3/c16-8-10-1-3-12(4-2-10)19-13-5-6-14-11(7-13)9-18-15(14)17/h1-7,17H,9H2
InChI Key USZAGAREISWJDP-UHFFFAOYSA-N
Bioactivity Comments
Inhibits partially purified human PDE4 with an IC50 of 490nM, and inhibits cytokine release in vitro and in vivo [1].
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
phosphodiesterase 7A Hs Inhibitor Inhibition 6.1 pIC50 - 1
pIC50 6.1 (IC50 7.3x10-7 M) [1]
phosphodiesterase 1A Hs Inhibitor Inhibition 5.2 pIC50 - 1
pIC50 5.2 (IC50 6.1x10-6 M) [1]
phosphodiesterase 4B Hs Inhibitor Inhibition - - - 1
[1]