Crisaborole
Grundinformationen
- CAS
2268785-42-6- Standard-SMILES
N#Cc1ccc(Oc2ccc3c(c2)COB3O)cc1- InChIKey
USZAGAREISWJDP-UHFFFAOYSA-N- Summenformel
- C14H10BNO3
- Durchschnittliche Molmasse
- 251,05 g/mol
Überblick
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of the class of benzoxaboroles that is 5-hydroxy-1,3-dihydro-2,1-benzoxaborole in which the phenolic hydrogen has been replaced by a 4-cyanophenyl group.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 non-steroidal anti-inflammatory drug, an antipsoriatic and a phosphodiesterase IV inhibitor. It is a nitrile, an aromatic ether and a benzoxaborole.
Namen und Bezeichner
- Bevorzugter Name
- Crisaborole
- IUPAC
- 4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzonitrile
- Englischer Name
- Crisaborole Impurity 16
- Summenformel
- C14H10BNO3
- Molmasse
- 251.05
Namen und Synonyme
Crisaborole906673-24-3AN-2728AN2728EucrisaAN 2728StaquiscrisaborolCrisaborole topical ointment 2%Q2R47HGR7P4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzonitrile4-[(1-hydroxy-1,3-dihydro-2,1-benzoxaborol-5-yl)oxy]benzonitrile
Weitere Namen anzeigen
Cortodoxone-d5Crisaborole Impurity 16
CHEBI:134677DTXSID102382314-((1-Hydroxy-1,3-dihydrobenzo(c)(1,2)oxaborol-6-yl)oxy)benzonitrileBenzonitrile, 4-((1,3-dihydro-1-hydroxy-2,1-benzoxaborol-5-yl)oxy)-crisaborolum4-((1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy)benzonitrile4-((1-hydroxy-1,3-dihydro-2,1-benzoxaborol-5-yl)oxy)benzonitrileRefChem:58963
Datenbank-Bezeichner
- CAS
2268785-42-6- ChEMBL
CHEMBL484785- ChEBI
CHEBI:134677- UNII
- Q2R47HGR7P
- EC Number
- 696-120-1
- Nikkaji
- J2.809.141I
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 62,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 19
- Formalladung
- 0
- Komplexität
- 361
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
SolubilityInsoluble
Human Drugs
Breast Feeding; Lactation; Milk, Human; Enzyme Inhibitors; Phosphodiesterase Inhibitors
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physikochemische Eigenschaften
- Aggregatzustand
- Solid
- Farbe
- Off-white to light yellow
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 6.5% (2 of 31) of reports.
Warning
H302 (93.5%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 31 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (93.5%)
Toxikologische Informationen
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Chemie und Industrie
Pharmakologische Informationen
ATC Code
D - Dermatologicals
QD - Dermatologicals
Protein BindingBased on an in vitro study, crisaborole is 97% bound to human plasma proteins
Pharmacodynamics
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.
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.
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.
FDA Pharmacological Classification
Q2R47HGR7P
CRISABOROLE
Established Pharmacologic Class [EPC] - Phosphodiesterase 4 Inhibitor
Mechanisms of Action [MoA] - Phosphodiesterase 4 Inhibitors
Crisaborole is a Phosphodiesterase 4 Inhibitor. The mechanism of action of crisaborole is as a Phosphodiesterase 4 Inhibitor.
CRISABOROLE
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