(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase编号: 134258
• 分子式: C22H28F2O5
• 平均质量: 410.4515264
• 单一同位素质量: 410.19048044
• SMILES: C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)F
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F
• InChI: InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1
• InChIKey: WXURHACBFYSXBI-GQKYHHCASA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC传统名: flumethasone
• 别名: 6α,9α-Difluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione; 6α,9α-Difluoro-16α-methylprednisolone; 6α-Fluorodexamethasone; Flumethasone; (6α,11β,16α)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 6α-Fluorodexamethazone; Anaprime; Aniprime; Aniprome; Cortexillar; Flucort; Flucorticin; Flumetasone; Flumethason; Fluvet; Methagon; NSC 5402; NSC 54702; RS 2177; U 10974; Vecort; Flumethasone

登记号

• CAS号: 2135-17-3
• EC号: 218-370-9
• MDL号: MFCD00056464
• PubChem SID: 24894998; 162228535
• PubChem CID: 16490

理论计算性质

• Acid pKa: 12.418192
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 1.3418503
• LogD (pH = 7.4): 1.3418462
• Log P: 1.3418504
• 摩尔折射率: 102.3163 cm^3
• 极化性: 39.40079 Å^3
• 极化表面积: 94.83 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: White Solid
• 熔点: 237-240°C

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: TU3832000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40
• 安全公开号: 22-36
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351
• GHS警示性声明: P281
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• 保存温度: 2-8°C

详细说明

Sigma Aldrich - F9507

Application
Flumethasone pivalate is a topical corticosteroid. Prompt decrease in inflammation, exudation and itching is experienced after application. It is a difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. Flumethasone is a corticosteroid commonly used in veterinary practice1 and has been used in cortisol assays to study early porcine conceptus development2.
Biochem/physiol Actions
Flumethasone is a glucocorticoid receptor agonist used in studies on plasma transcortin binding.
Flumethasone is a glucocorticoid receptor agonist. It binds to the nucleus causing a variety of genetic activation and repressions. The anti-inflammatory actions of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding .

Toronto Research Chemicals - F455000

A glucocorticoid. An anti-inflammatory.

参考文献

• Matuszewski, B, et al.: Anal. Chem., 75, 3019 (2003)
• Fekete, S., et al.: J. Pharm. Biomed. Anal., 49, 64 (2003)