crisaborole   Click here for help

GtoPdb Ligand ID: 9151

Synonyms: AN 2728 | AN2728 | compound 5b [PMID: 19303290] | Eucrisa® | Staquis®
Approved drug Immunopharmacology Ligand
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.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2016), EMA (2020))
IUPAC Name Click here for help
4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzonitrile
International Nonproprietary Names Click here for help
INN number INN
10024 crisaborole
Synonyms Click here for help
AN 2728 | AN2728 | compound 5b [PMID: 19303290] | Eucrisa® | Staquis®
Database Links Click here for help
BindingDB Ligand 50277665
CAS Registry No. 906673-24-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL484785
DrugCentral Ligand 5201
GtoPdb PubChem SID 315661236
PubChem CID 44591583
Search Google for chemical match using the InChIKey USZAGAREISWJDP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone USZAGAREISWJDP
Search PubMed clinical trials crisaborole
Search PubMed titles crisaborole
Search PubMed titles/abstracts crisaborole
UniChem Compound Search for chemical match using the InChIKey USZAGAREISWJDP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey USZAGAREISWJDP-UHFFFAOYSA-N
Wikipedia Crisaborole