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Merck
CN

PZ0037

Crisaborole

≥98% (HPLC), phosphodiesterase 4 (PDE4) inhibitor, powder

Synonym(s):

4-[(1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]benzonitrile, 5-(4-Cyanophenoxy)-1,3-dihydro-1-hydroxy-[2,1]-benzoxaborole, 5-(4-Cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole, AN2728

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About This Item

Empirical Formula (Hill Notation):
C14H10BNO3
CAS Number:
906673-24-3
Molecular Weight:
251.05
NACRES:
NA.77
UNSPSC Code:
12352200
MDL number:
MFCD17169940

Key Documents

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Product Name

Crisaborole, ≥98% (HPLC)

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

SMILES string

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

InChI key

USZAGAREISWJDP-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

room temp

Quality Level

100

Related Categories

Biochem/physiol Actions

Crisaborole is a non-steroidal anti-inflammatory phosphodiesterase 4 (PDE4) inhibitor.
Crisaborole is a non-steroidal anti-inflammatory phosphodiesterase 4 (PDE4) inhibitor. Crisaborole has an IC50 value of 490 nM for PDE4 with similar IC50 values for release of cytokines TNF-α, IL-2, and IFN-γ, and shows little inhibition against other PDE isozymes. Crisaborole has been approved as a topical treatment for atopic dermatitis.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000489030
0000489029
0000489029
0000489030
0000359275

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Chen Dong et al.
The Journal of pharmacology and experimental therapeutics, 358(3), 413-422 (2016-06-30)
Psoriasis and atopic dermatitis are skin diseases affecting millions of patients. Here, we characterize benzoxaborole phosphodiesterase (PDE)-4 inhibitors, a new topical class that has demonstrated therapeutic benefit for psoriasis and atopic dermatitis in phase 2 or phase 3 studies. Crisaborole
Tsutomu Akama et al.
Bioorganic & medicinal chemistry letters, 19(8), 2129-2132 (2009-03-24)
A series of phenoxy benzoxaboroles were synthesized and screened for their inhibitory activity against PDE4 and cytokine release. 5-(4-Cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2728) showed potent activity both in vitro and in vivo. This compound is now in clinical development for the topical treatment

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