Crisaborole

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Crisaborole
Crisaborole.svg
Clinical data
Trade namesEucrisa, /jˈkrɪsə/ yoo-KRIS
Routes of
administration
Topical (ointment)
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.225.309 Edit this at Wikidata
Chemical and physical data
FormulaC14H10BNO3
Molar mass251.045 g/mol g·mol−1
3D model (JSmol)

Crisaborole, sold under the brand name Eucrisa, is a nonsteroidal topical medication used for the treatment of mild-to-moderate atopic dermatitis (eczema) in people two years or older.[1][2] It was approved by U.S. Food and Drug Administration on Dec 14, 2016[3] and June 6, 2018 by Health Canada[4].

Side effects[edit]

At the site of application, crisaborole may cause burning or stinging. Rarely, there may be an allergic reaction.[5]

Pharmacology[edit]

Pharmacodynamics[edit]

Crisaborole is a phosphodiesterase-4 inhibitor, mainly acting on phosphodiesterase 4B (PDE4B), which causes inflammation.[6] Chemically, crisaborole is a phenoxybenzoxaborole.[6] Inhibition of PDE4B appears to suppress the release of tumor necrosis factor alpha (TNFα), interleukin-12 (IL-12), IL-23 and other cytokines, proteins believed to be involved in the immune response and inflammation.[6]

Chemistry[edit]

Crisaborole (chemical name: 4-[(1-hydroxy-1,3-dihydro-2,1-benzoxaborol-5-yl)oxy]benzonitrile) is a member of the class of benzoxaboroles characterized by the presence of a boronic acid hemiester with a phenolic ether and a nitrile.[7] Crisaborole crystallizes into two polymorphs that differ in the conformation of the oxaborole ring. A cocrystal with 4,4'-bipyridine has been prepared and studied by X-ray crystallography.[8]

History[edit]

Crisaborole was developed by Anacor Pharmaceuticals for the topical treatment of psoriasis.[9][6][10] During preclinical and clinical development, crisaborole was called AN2728 and PF-06930164.[11]

See also[edit]

References[edit]

  1. ^ "FDA Approves Eucrisa for Eczema". U.S. Food and Drug Administration. 14 December 2016.
  2. ^ "Eucrisa (crisaborole) Ointment, 2%, for Topical Use. Full Prescribing Information". Anacor Pharmaceuticals, Inc. Palo Alto, CA 94303 USA. Retrieved 17 December 2016.
  3. ^ "FDA approves Eucrisa for eczema" (Press release). U.S. Food and Drug Administration. December 14, 2016.
  4. ^ Government of Canada. "Regulatory Decision Summary - Eucrisa - Health Canada". Health Canada. Archived from the original on 2019-09-14. Retrieved 2019-09-14.
  5. ^ "PRODUCT MONOGRAPH" (PDF). Government of Canada. 2018-06-07. Archived (PDF) from the original on 2019-04-07. Retrieved 2019-04-07.
  6. ^ a b c d Moustafa, F; Feldman, SR (16 May 2014). "A Review of Phosphodiesterase-Inhibition and the Potential Role for Phosphodiesterase 4-Inhibitors in Clinical Dermatology" (PDF). Dermatology Online Journal. 20 (5): 22608. PMID 24852768.
  7. ^ "WHO Drug Information, Vol. 29, No. 3, 2015. International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 74" (PDF). World Health Information. p. 391. Retrieved 26 April 2016.
  8. ^ Campillo-Alvarado, Gonzalo; Didden, Tighe D.; Oburn, Shalisa M.; Swenson, Dale C.; MacGillivray, Leonard R. (2018). "Exploration of Solid Forms of Crisaborole: Crystal Engineering Identifies Polymorphism in Commercial Sources and Facilitates Cocrystal Formation". Crystal Growth & Design. 18 (8): 4416–4419. doi:10.1021/acs.cgd.8b00375. ISSN 1528-7483.
  9. ^ Nazarian, R; Weinberg, JM (November 2009). "AN-2728, a PDE4 Inhibitor for the Potential Topical Treatment of Psoriasis and Atopic Dermatitis". Current Opinion in Investigational Drugs. 10 (11): 1236–42. PMID 19876791.
  10. ^ Spreitzer, H (16 August 2016). "Neue Wirkstoffe: Crisaborol". Österreichische Apotheker-Zeitung (in German) (17/2016).
  11. ^ "Crisaborole". AdisInsight. Retrieved 24 July 2017.