Crisaborole
- Product Name
- Crisaborole
- CAS No.
- 906673-24-3
- Chemical Name
- Crisaborole
- Synonyms
- 4-[(1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]benzonitrile AN 2728;AN 2728;CS-1895;Cleboro;Creborol;PF-06930164;Crisaborole;AN-2728, >=98%;AN2728/AN-2728;Crisaborole EP
- CBNumber
- CB42518350
- Molecular Formula
- C14H10BNO3
- Formula Weight
- 251.05
- MOL File
- 906673-24-3.mol
Crisaborole Property
- Melting point:
- >130°C (softened)
- Boiling point:
- 425.9±55.0 °C(Predicted)
- Density
- 1.33±0.1 g/cm3(Predicted)
- storage temp.
- room temp
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- powder
- pka
- 7.00±0.20(Predicted)
- color
- white to beige
- Stability:
- Hygroscopic
- 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
- InChIKey
- USZAGAREISWJDP-UHFFFAOYSA-N
- SMILES
- C(#N)C1=CC=C(OC2=CC=C3B(O)OCC3=C2)C=C1
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P311Call a POISON CENTER or doctor/physician.
N-Bromosuccinimide Price
- Product number
- PZ0037
- Product name
- Crisaborole
- Purity
- ≥98% (HPLC)
- Packaging
- 5MG
- Price
- $102
- Updated
- 2023/06/20
- Product number
- PZ0037
- Product name
- Crisaborole
- Purity
- ≥98% (HPLC)
- Packaging
- 25MG
- Price
- $413
- Updated
- 2023/06/20
- Product number
- 21455
- Product name
- AN2728
- Purity
- ≥98%
- Packaging
- 25mg
- Price
- $62
- Updated
- 2024/03/01
- Product number
- 21455
- Product name
- AN2728
- Purity
- ≥98%
- Packaging
- 50mg
- Price
- $115
- Updated
- 2024/03/01
- Product number
- 21455
- Product name
- AN2728
- Purity
- ≥98%
- Packaging
- 100mg
- Price
- $216
- Updated
- 2024/03/01
Crisaborole Chemical Properties,Usage,Production
Description
Crisaborole is a phosphodiesterase- 4 (PDE4) inhibitor that was approved by FDA on December 14, 2016 as Eucrisa, a topical treatment of for mild to moderate atopic dermatitis (AD) in patients aged two years and older. The drug, which was developed by Anacor Pharmaceuticals and later acquired and marketed by Pfizer, is delivered as a 2% ointment, which is applied topically. Its structure contains a boron atom, which facilitates skin penetration and binding to the bimetal center of the phosphodiesterase 4 enzyme. The unique employment of boron within the chemical structure of the drug is designed to enable selective engagement of PDE4 (an enzyme involved in the conversion of cAMP into AMP, which signals for downstream inflammatory events), effective penetration of the drug through human skin, and rapid clearance to limit systemic circulation.
Uses
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. AN2728 is being studied as an anti-inflammatory agent.
Definition
ChEBI: Crisaborole is a member of the class of benzoxaboroles that is 5-hydroxy-1,3-dihydro-2,1-benzoxaborole in which the phenolic hydrogen has been replaced by a 4-cyanophenyl group. A phosphodiesterase 4 inhibitor that is used for treatment of mild to moderate atopic dermatitis in children and adults. It has a role as a phosphodiesterase IV inhibitor, an antipsoriatic and a non-steroidal anti-inflammatory drug. It is a benzoxaborole, an aromatic ether and a nitrile. ?
Biochem/physiol Actions
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.
Side effects
EUCRISA may cause side effects.
Allergic reactions. EUCRISA may cause allergic reactions at or near the application site. These can be serious and may include hives, itching, swelling, and redness.
www.eucrisa.com
Synthesis
Several disclosures describing synthetic approaches to ethereal boron-containing anti-inflammatory compounds have been published by Anacor. Commercially available bromobenzaldehyde 134 was protected as the corresponding acetal upon subjection to warm ethylene glycol in the presence of catalytic p-toluenesulfonic acid. This was followed by nucleophilic aromatic substitution involving 4-fluorobenzonitrile and subsequent acetal deprotection to furnish diaryl ether 136. Although multiple approaches to crisaborole have been reported from this intermediate diaryl ether 136, the published literature approach involves the following sequence: reduction of the aldehyde with sodium borohydride followed by THP protection to furnish bromobenzene 137, which then underwent lithium-halogen exchange prior to quenching with triisopropyl borate and acidification to arrive at crisaborole (XIII). Alternatively, patents from Anacor describe a general approach employing a Miyaura coupling of 136, enabling the installation of the corresponding pincacol borane, which could then be exposed to reduction conditions using sodium borohydride followed by boric acid wash, aqueous workup, and lyophilization to furnish XIII.
Mode of action
Crisaborole is a Phosphodiesterase 4 Inhibitor. The mechanism of action of crisaborole is as a Phosphodiesterase 4 Inhibitor.
Crisaborole Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Crisaborole manufacturers
- Product
- Crisaborole 906673-24-3
- Price
- US $0.00/KG
- Min. Order
- 10g
- Purity
- 99%min
- Supply Ability
- 10kg
- Release date
- 2021-09-13
- Product
- Crisaborole 906673-24-3
- Price
- US $100.00-80.00/KG
- Min. Order
- 1KG
- Purity
- 99.9%
- Supply Ability
- 1000
- Release date
- 2024-05-13
- Product
- Crisaborole 906673-24-3
- Price
- US $0.00-0.00/g
- Min. Order
- 10g
- Purity
- 99% HPLC
- Supply Ability
- 10000
- Release date
- 2024-09-21