클로코르톨론
Clocortolone
기본 정보
- CAS
34097-16-0- 표준 SMILES
C[C@@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(Cl)[C@@H](O)C[C@]2(C)[C@H]1C(=O)CO- InChIKey
YMTMADLUXIRMGX-RFPWEZLHSA-N- 분자식
- C22H28ClFO4
- 평균 분자량
- 410.9 g/mol
- 단동위원소 질량
- 410.1660152
개요
Clocortolone is 16alpha-Methylpregna-1,4-diene-3,20-dione bearing hydroxy substituents at the 11beta and 21 positions, fluorine at position 6 and chlorine at position 9. A medium potency corticosteroid, it is used as its 21-O-pivalate or caproate ester for the relief of inflammatory and pruritic (itching) skin disorders. It has a role as an anti-inflammatory drug and an antipruritic drug. It is a primary alpha-hydroxy ketone, a glucocorticoid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid, a 3-oxo-Delta(1),Delta(4)-steroid and a chlorinated steroid.
이름 및 식별자
- 우선 이름
- Clocortolone
- IUPAC
- (6S,8S,9R,10S,11S,13S,14S,16R,17S)-9-chloro-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-3-one
- 현지명
- 클로코르톨론
- 영어명
- Clocortolone
- 분자식
- C22H28ClFO4
- 분자량
- 410.91
이름 및 동의어
CLOCORTOLONE4828-27-7ClocortolonaClocortolonumN8ZUB7XE0HCHEBI:595829-chloro-6alpha-fluoro-11beta,21-dihydroxy-16alpha-methyl-1,4-pregnadien-3,20-dione9-chloro-6alpha-fluoro-16alpha-methyl-1,4-pregnadiene-11beta,21-diol-3,20-dione(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo(8.7.0.0^(2,7).0^(11,15))heptadeca-3,6-dien-5-one(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-oneRefChem:57256D07AB21
이름 더 보기
클로코르톨론9-ChlorClocortolonFluocortolone Impurity 99-Chloro-6α-fluoro-11β,21-dihydroxy-17α-Methylpregna-1,4-diene-3,20-dione9-Chloro-6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione(6α,11β,16α)-9-Chloro-6-fluoro-11,21-dihydroxy-16-Methylpregna-1,4-diene-3,20-dionePregna-1,4-diene-3,20-dione, 9-chloro-6-fluoro-11,21-dihydroxy-16-methyl-, (6α,11β,16α)-
물성
구조 계산 물성
- XLogP
- 2.5
- 극성 표면적
- 74.6 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 5
- 회전 가능 결합 수
- 2
- 무거운 원자 수
- 28
- 형식 전하
- 0
- 복잡도
- 793
실험 및 물리화학적 성질
DrugsPharmaceuticals -> Listed in ZINC15
LogP3.8
Solubility1.50e-02 g/L
Physical DescriptionSolid
물리화학적 성질
- 녹는점
- 254 ° · 254° (dec)
- 끓는 점
- 566 · 566.0±50.0 °C(Predicted)
- 밀도
- 1.32 · 1.32±0.1 g/cm3(Predicted)
- 저장 조건
- Refrigerator, Under Inert Atmosphere
- 용해도
- 클로로포름(약간), 디옥산(약간), DMSO(약간), 메탄올(약간) 에 용해됨
- 물리적 상태
- 고체
- 산도 계수 (pKa)
- 12.98 · 12.98±0.10(Predicted)
- 색상
- 흰색에서 밝은 노란색
화학 및 산업
약리 정보
ATC Code
D - Dermatologicals
QD - Dermatologicals
Pharmacodynamics
Like other topical corticosteroids, clocortolone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Clocortolone is a moderate potency topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
Mechanism of Action
The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A<sub>2</sub> inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A<sub>2</sub>. These enzyme transcriptional changes are mediated by the drug binding first to the glucocorticoid receptor. This complex can migrate to the cell nucleus which then binds to DNA initiating genetic activation and repression of various genes.
Metabolism/MetabolitesMetabolized, primarily in the liver, and then excreted by the kidneys.
FDA Pharmacological Classification
N8ZUB7XE0H
CLOCORTOLONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Clocortolone is a Corticosteroid. The mechanism of action of clocortolone is as a Corticosteroid Hormone Receptor Agonist.
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
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