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    Crisaborole

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    2D Structure
    Also known as: 906673-24-3, An-2728, An2728, 4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)oxy)benzonitrile, Eucrisa, An 2728
    Molecular Formula
    C14H10BNO3
    Molecular Weight
    251.05  g/mol
    InChI Key
    USZAGAREISWJDP-UHFFFAOYSA-N
    FDA UNII
    Q2R47HGR7P
    Crisaborole is a novel oxaborole approved by FDA on December 14, 2016 as Eucrisa, a topical treatment of for mild to moderate atopic dermatitis. This non-steroidal agent is efficacious in improving disease severity, reducing the risk of infection and reducing the signs and symptoms in patients 2 years old and older. It reduces the local inflammation in the skin and prevents further exacerbation of the disease with a good safety profile. Its structure contains a boron atom, which facilitates skin penetration and binding to the bimetal center of the phosphodiesterase 4 enzyme. It is currently under development as topical treatment of psoriasis.
    Crisaborole is a Phosphodiesterase 4 Inhibitor. The mechanism of action of crisaborole is as a Phosphodiesterase 4 Inhibitor.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzonitrile
    2.1.2 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
    2.1.3 InChI Key
    USZAGAREISWJDP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    B1(C2=C(CO1)C=C(C=C2)OC3=CC=C(C=C3)C#N)O
    2.2 Other Identifiers
    2.2.1 UNII
    Q2R47HGR7P
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole

    2. An-2728

    3. An2728

    4. Eucrisa

    2.3.2 Depositor-Supplied Synonyms

    1. 906673-24-3

    2. An-2728

    3. An2728

    4. 4-((1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)oxy)benzonitrile

    5. Eucrisa

    6. An 2728

    7. Crisaborole (an2728)

    8. 5-(4-cyanophenoxy)-2,3-dihydro-1-hydroxy-2,1-benzoxaborole

    9. 4-[(1-hydroxy-3h-2,1-benzoxaborol-5-yl)oxy]benzonitrile

    10. Crisaborole Topical Ointment 2%

    11. Q2r47hgr7p

    12. 4-((1-hydroxy-1,3-dihydrobenzo-[c][1,2]oxaborol-5-yl)oxy)benzonitrile

    13. Chembl484785

    14. Mfcd17169940

    15. 4-((1-hydroxy-1,3-dihydrobenzo(c)(1,2)oxaborol-6-yl)oxy)benzonitrile

    16. 906673-25-4

    17. Staquis

    18. 4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzonitrile

    19. 4-[(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy]benzonitrile

    20. 4-[(1-hydroxy-1,3-dihydro-2,1-benzoxaborol-5-yl)oxy]benzonitrile

    21. Benzonitrile, 4-((1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy)-

    22. 4-[(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yl)oxy]benzonitrile

    23. Crisaborole [usan]

    24. Unii-q2r47hgr7p

    25. Crisaborole [inn]

    26. Eucrisa (tn)

    27. Crisaborole [mi]

    28. Crisaborole (usan/inn)

    29. Crisaborole [usan:inn]

    30. Crisaborole(an-2728)

    31. Crisaborole [who-dd]

    32. Schembl595261

    33. Gtpl9151

    34. Crisaborole, >=98% (hplc)

    35. Crisaborole [orange Book]

    36. Dtxsid10238231

    37. Tqp0866

    38. Chebi:134677

    39. Bcp08677

    40. Ex-a1087

    41. Bdbm50277665

    42. Akos016005425

    43. Zinc169748244

    44. Ccg-266972

    45. Cs-1057

    46. Db05219

    47. Sb16802

    48. Compound 5b [pmid: 19303290]

    49. Ncgc00345792-01

    50. Ncgc00345792-02

    51. Ncgc00345792-04

    52. Ac-30331

    53. As-70551

    54. Hy-10978

    55. Sy113089

    56. Db-078771

    57. Ft-0767999

    58. S5014

    59. Pf-06930164

    60. C90571

    61. C90670

    62. D10873

    63. F51164

    64. 5-(4-cyanophenoxy)-1-hydroxy-2,1-benzoxaborole

    65. Q21098894

    66. Crisaborole;4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)benzonitrile;an-2728

    67. 1073669-75-6

    2.4 Create Date
    2010-01-26
    3 Chemical and Physical Properties
    Molecular Weight 251.05 g/mol
    Molecular Formula C14H10BNO3
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass251.0753733 g/mol
    Monoisotopic Mass251.0753733 g/mol
    Topological Polar Surface Area62.5 Ų
    Heavy Atom Count19
    Formal Charge0
    Complexity361
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Intended for the topical treatment of mild to moderate atopic dermatitis in patients 2 years of age and older.

    FDA Label

    Staquis is indicated for treatment of mild to moderate atopic dermatitis in adults and paediatric patients from 2 years of age with 40% body surface area (BSA) affected.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Crisaborole has broad-spectrum anti-inflammatory activity by mainly targeting phosphodiesterase 4 (PDE4) enzyme that is a key regulator of inflammatory cytokine production. As this enzyme is expressed in keratinocytes and immune cells, crisaborole mediates an anti-inflammatory effect on almost all inflammatory cells. Topical application of this drug is useful as it potentiates the localization of this drug in the skin and this anti-inflammatory activity is in the low micromolar range.

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    CRISABOROLE
    5.2.2 FDA UNII
    Q2R47HGR7P
    5.2.3 Pharmacological Classes
    Phosphodiesterase 4 Inhibitors [MoA]; Phosphodiesterase 4 Inhibitor [EPC]
    5.3 ATC Code

    D11AH06

    D - Dermatologicals

    D11 - Other dermatological preparations

    D11A - Other dermatological preparations

    D11AH - Agents for dermatitis, excluding corticosteroids

    D11AH06 - Crisaborole

    5.4 Absorption, Distribution and Excretion

    Absorption

    Systemic concentrations of crisaborole were reached by 8 days of twice-daily topical administration. It has low systemic absorption thus poses less risk for developing systemic side effects.

    Route of Elimination

    Renal excretion of metabolites is the major route of elimination.

    5.5 Metabolism/Metabolites

    Crisaborole is substantially metabolized into inactive metabolites. The major metabolite 5-(4-cyanophenoxy)-2-hydroxyl benzylalcohol (metabolite 1), is formed via hydrolysis; this metabolite is further metabolized into downstream metabolites, among which 5-(4-cyanophenoxy)-2-hydroxyl benzoic acid (metabolite 2), formed via oxidation, is also a major metabolite.

    5.6 Mechanism of Action

    Inhibition of PDE4 by crisaborole leads to elevated levels of cyclic adenosine monophosphate (cAMP). Increased intracellular levels of cAMP inhibit the NF-kB pathway and suppress the release of pro-inflammatory mediators such as TNF-alfa and various interleukins that play a causative role in psoriasis and atopic dermatitis. Suppression of downstream effects in different cell types may explain the therapeutic role of crisaborole in immune-mediated skin diseases.