기본 정보
- CAS
2268785-42-6- 표준 SMILES
N#Cc1ccc(Oc2ccc3c(c2)COB3O)cc1- InChIKey
USZAGAREISWJDP-UHFFFAOYSA-N- 분자식
- C14H10BNO3
- 평균 분자량
- 251.05 g/mol
개요
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of the class of benzoxaboroles that is 5-hydroxy-1,3-dihydro-2,1-benzoxaborole in which the phenolic hydrogen has been replaced by a 4-cyanophenyl group.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.
이름 및 식별자
- 우선 이름
- Crisaborole
- IUPAC
- 4-[(1-hydroxy-3H-2,1-benzoxaborol-5-yl)oxy]benzonitrile
- 영어명
- Crisaborole Impurity 16
- 분자식
- C14H10BNO3
- 분자량
- 251.05
이름 및 동의어
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
이름 더 보기
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
데이터베이스 식별자
- CAS
2268785-42-6- ChEMBL
CHEMBL484785- ChEBI
CHEBI:134677- UNII
- Q2R47HGR7P
- EC Number
- 696-120-1
- Nikkaji
- J2.809.141I
물성
구조 계산 물성
- 극성 표면적
- 62.5 Ų
- 수소 결합 공여자 수
- 1
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 19
- 형식 전하
- 0
- 복잡도
- 361
실험 및 물리화학적 성질
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
물리화학적 성질
- 물리적 상태
- Solid
- 색상
- Off-white to light yellow
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
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.
유해성 정보
Hazard Classes and CategoriesAcute Tox. 4 (93.5%)
독성 정보
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
화학 및 산업
약리 정보
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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