基本情報
- CAS
2557-49-5- 標準SMILES
C[C@H]1C[C@H]2[C@@H]3C[C@H](F)C4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@]2(C)[C@@]1(O)C(=O)CO- InChIKey
WXURHACBFYSXBI-XHIJKXOTSA-N- 分子式
- C22H28F2O5
- 平均分子量
- 410.5 g/mol
- 単同位体質量
- 410.19048031
概要
Diflorasone is the 16beta-analogue of flumethasone. It is used as the 17,21-diacetate as a topical anti-inflammatory and antipruritic in the treatment of various skin disorders. It has a role as an anti-inflammatory drug. It is a primary alpha-hydroxy ketone, a tertiary alpha-hydroxy ketone, a glucocorticoid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, an 11beta-hydroxy steroid, a 20-oxo steroid, a fluorinated steroid and a 3-oxo-Delta(1),Delta(4)-steroid. It derives from a hydride of a pregnane.
名称と識別子
- 優先名称
- Diflorasone
- IUPAC
- (6S,8S,9R,10S,11S,13S,14S,16S,17R)-6,9-difluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
- 現地名
- ジフロラゾン
- 英語名
- Diflorasone
- 分子式
- C22H28F2O5
- 分子量
- 410.46
名称と別名
diflorasone2557-49-5DiflorasonaDiflorasonumMurodeT2DHJ9645W6alpha,9-Difluoro-11beta,17,21-trihydroxy-16beta-methylpregna-1,4-diene-3,20-dioneCHEBI:59750DTXSID201036185(6alpha,11beta,16beta)-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-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,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
名称をさらに表示
6α,9-ジフルオロ-11β,17,21-トリヒドロキシ-16β-メチルプレグナ-1,4-ジエン-3,20-ジオンジフロラゾンジフロラソン(1R,2S,3aS,3bS,5S,9aS,9bR,10S,11aS)-5,9b-ジフルオロ-1,10-ジヒドロキシ-1-(2-ヒドロキシアセチル)-2,9a,11a-トリメチル-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-シクロペンタ[a]フェナントレン-7-オンDifloasoneDiflorasone [INN:BAN]Diflorasone USP/EP/BPDiflorasone, 10 mM in DMSO
物性
構造計算による物性
- XLogP
- 1.9
- 極性表面積
- 94.8 Ų
- 水素結合供与体数
- 3
- 水素結合受容体数
- 7
- 回転可能結合数
- 2
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 839
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.1
Solubility8.53e-02 g/L
Human DrugsBreast Feeding; Lactation; Corticosteroids, Topical; Glucocorticoids; Anti-Inflammatory Agents
Physical DescriptionSolid
物理化学的性質
- 融点
- 228 · 228-239°C
- 沸点
- 569.8 · 569.8±50.0 °C(Predicted)
- 比重(密度)
- 1.36 · 1.36±0.1 g/cm3(Predicted)
- 貯蔵温度
- Refrigerator
- 溶解性
- メタノール（わずかに）
- 酸解離定数(Pka)
- 11.98 · 11.98±0.70(Predicted)
- 外見
- 個体
- 色
- オフホワイトからペールイエロー
- InChIKey
- WXURHACBFYSXBI-NFELDLQGNA-N
- SMILES
- F[C@]12[C@H](C[C@@]3([C@@](O)(C(=O)CO)[C@@H](C)C[C@@]3([H])[C@]1([H])C[C@H](F)C1=CC(=O)C=C[C@]21C)C)O |&1:1,2,4,5,11,14,16,19,27,r|
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Warning
H312 (60%): Harmful in contact with skin [Warning Acute toxicity, dermal]
P203, P260, P264, P264+P265, P270, P280, P302+P352, P305+P351+P338, P308+P316, P317, P318, P321, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 5 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazard Classes and CategoriesAcute Tox. 4 (60%)
毒性情報
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
安全データ
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H312
化学と産業
薬理情報
ATC Code
D - Dermatologicals
QD - Dermatologicals
Protein BindingBound to plasma proteins in varying degrees.
Pharmacodynamics
Like other topical corticosteroids, diflorasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Diflorasone is a potent 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>.
Metabolism/MetabolitesMetabolized, primarily in the liver, and then excreted by the kidneys.
FDA Pharmacological Classification
T2DHJ9645W
DIFLORASONE
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Diflorasone is a Corticosteroid. The mechanism of action of diflorasone is as a Corticosteroid Hormone Receptor Agonist.
MeSH Pharmacological Classification
Substances that reduce or suppress INFLAMMATION.
A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system.
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