Introduction：Basic information about CAS 906673-24-3|AN-2728, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | AN-2728 |
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| CAS Number | 906673-24-3 | Molecular Weight | 251.045 |
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| Density | 1.3±0.1 g/cm3 | Boiling Point | 425.9±55.0 °C at 760 mmHg |
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| Molecular Formula | C14H10BNO3 | Melting Point | / |
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| MSDS | / | Flash Point | 211.4±31.5 °C |
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Names
| Name | 4-((1-Hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)oxy)benzonitrile |
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| Synonym | More Synonyms |
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AN-2728 BiologicalActivity
| Description | Crisaborole (AN-2728) is a potent inhibitor of PDE4 and cytokine release; inhibit PDE4 with an IC50 of 0.49 μM. |
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| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>Phosphodiesterase (PDE)Research Areas >>Inflammation/Immunology |
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| Target | IC50: 0.49 μM (PDE4)[1] |
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| In Vitro | Crisaborole (AN-2728) inhibits PDE4, TNF-α, IL-2, IFN-γ, IL-5 and IL-10 with IC50 values of 0.49, 0.54, 0.61, 0.83, 2.4 and 5.3 μM. Crisaborole (AN-2728) shows the most potent activity against PDE4 catalytic domain, but it also shows inhibition against PDE1A3, PDE3Cat, and PDE7A1. Crisaborole (AN-2728) inhibits PDE isozymes PDE1A3, PDE3Cat , PDE4Cat and PDE7A1 with IC50 values of 6.1, 6.4, 0.11 and 0.73 μM[1]. Crystallography reveals that interaction of benzoxaboroles with the hydrophobic pocket in the PDE4 catalytic domain increase their affinity for PDE4. These benzoxaboroles strongly suppresses the secretion of cytokines associated with Ps and AD[2]. Crisaborole (AN-2728) is a topically administered, boron-containing, anti-inflammatory compound that inhibits PDE4 activity and thereby suppresses the release of TNFalpha, IL-12, IL-23 and other cytokines[3]. |
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| In Vivo | Crisaborole (AN-2728) shows significant inhibition against the ear edema caused by phorbol ester after dosing at 1 mg/ear×2 (78% and 68%, respectively). The efficacy is comparable to that of dexamethasone, suggesting that Crisaborole (AN-2728) has good anti-inflammatory activity as well as skin penetration[1]. Crisaborole (AN-2728) is reported to be well tolerated and to demonstrate significant effects on markers of efficacy, with results that are comparable to positive controls in clinical trials[3]. |
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| References | [1]. Akama T, et al. Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis. Bioorg Med Chem Lett. 2009 Apr 15;19(8):2129-32. [2]. Nazarian R, et al. AN-2728, a PDE4 inhibitor for the potential topical treatment of psoriasis and atopic dermatitis. Curr Opin Investig Drugs. 2009 Nov;10(11):1236-42. [3]. Nazarian R, et al. AN-2728, a PDE4 inhibitor for the potential topical treatment of psoriasis and atopic dermatitis. Curr Opin Investig Drugs. 2009 Nov;10(11):1236-42. |
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Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
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| Boiling Point | 425.9±55.0 °C at 760 mmHg |
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| Molecular Formula | C14H10BNO3 |
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| Molecular Weight | 251.045 |
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| Flash Point | 211.4±31.5 °C |
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| Exact Mass | 251.075378 |
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| PSA | 62.48000 |
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| LogP | 1.56828 |
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| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
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| Index of Refraction | 1.629 |
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| InChIKey | USZAGAREISWJDP-UHFFFAOYSA-N |
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| SMILES | N#Cc1ccc(Oc2ccc3c(c2)COB3O)cc1 |
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| Storage condition | -20°C |
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Safety Information
Customs
| HS Code | 2926909090 |
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| Summary | HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0% |
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Synonyms
| AN2728 |
| AN-2728 |
| Crisaborole |
| UNII-Q2R47HGR7P |
| 4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzonitrile |
| Benzonitrile, 4-[(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]- |
| 4-[(1-Hydroxy-1,3-dihydro-2,1-benzoxaborol-5-yl)oxy]benzonitrile |
| 4-[(1,3-Dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]benzonitrile |
