Find Crisaborole manufacturers, exporters & distributors on PharmaCompass

Crisaborole

Synopsis, Chemistry

APIs // Active Pharmaceutical Ingredients

27 API Suppliers, 9 USDMF, 4 EU WC, 12 NDC API, 21 Listed Suppliers

DEVELOPMENTS

2 Drug(s) in Development

2 Drug(s) in Development

PRICE INFORMATION

API Reference Price, API Exports, API Imports

INTERMEDIATES

22 Suppliers

22 Suppliers

DOSSIERs // Finished Dosage Formulations

4 Dossiers, 1 FDA Orange Book, 1 Canada, 2 South Africa

RELATED EXCIPIENT COMPANIES

Suppliers, 5 Kerry, 2 BASF, 1 Nanjing Well Pharmaceutical, 1 Finar

EXCIPIENTS BY APPLICATIONS

5 Co-Processed Excipients, 3 Topical, 2 Solubilizers, 2 Film Formers & Plasticizers, 1 Thickeners and Stabilizers, 1 Fillers, Diluents & Binders, 1 Parenteral, 1 Coating Systems & Additives

GLOBAL SALES INFORMATION

7 US Medicaid Prescriptions

7 US Medicaid Prescriptions

MARKET PLACE

8 APIs

8 APIs

PATENTS

8 US Patents, 1 US Exclusivities

DIGITAL CONTENT

2 Data Compilations & Company Tracker #PharmaFlow, 9 News

API SUPPLIERS

API Suppliers

US DMFs Filed

CEP/COS Certifications

JDMFs Filed

Other Certificates

Other Suppliers

API REF. PRICE (USD / KG)

6,398

API Market Place

INTERMEDIATES

DOSSIERS // FDF

USA (Orange Book)

Europe

Canada

Australia

South Africa

Uploaded Dossiers

GLOBAL SALES (USD Million)

U.S. Medicaid

58.00

Annual Reports

147.00

FDF Market Place

EXCIPIENTS

PATENTS & EXCLUSIVITIES

USFDA Orange Book Patents

USFDA Exclusivities

DIGITAL CONTENT

Blog #PharmaFlow

News

REF STANDARD

EDQM

USP

Other Listed Suppliers

SERVICES

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

Crisaborole

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 Formula	C₁₄H₁₀BNO₃
Molecular Weight	251.05 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	251.0753733 g/mol
Monoisotopic Mass	251.0753733 g/mol
Topological Polar Surface Area	62.5 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	361
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.