2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase编号: 108
• 分子式: C26H32F2O7
• 平均质量: 494.5248864
• 单一同位素质量: 494.2116098
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](OC(=O)C)([C@H](C3)C)C(=O)COC(=O)C)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C
• Canonical SMILES: CC(=O)O[C@@]1([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)C(=O)COC(=O)C
• InChI: InChI=1S/C26H32F2O7/c1-13-8-17-18-10-20(27)19-9-16(31)6-7-23(19,4)25(18,28)21(32)11-24(17,5)26(13,35-15(3)30)22(33)12-34-14(2)29/h6-7,9,13,17-18,20-21,32H,8,10-12H2,1-5H3/t13-,17-,18-,20-,21-,23-,24-,25-,26-/m0/s1
• InChIKey: BOBLHFUVNSFZPJ-JOYXJVLSSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate; 2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate; 2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-14-(acetyloxy)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC传统名: diflorasone
• 商标名: Florone; Florone E; Maxiflor; Psorcon
• 别名: 6α,9-二氟-11β,17,21-三羟基-16β-甲基孕甾-1,4-二烯-3,20-二酮 17,21-二乙酸酯; 双氟拉松乙酸酯; Diflorasone diacetate; Diflorasone Diacetate; Diflorasone; 6α,9-Difluoro-11β,17,21-trihydroxy-16 β-methyl-pregna-1,4-diene-3,20-dione 17,21-diacetate; DIFLORASONE DIACETATE; (6α,11β,16β)-17,21-Bis(acetyloxy)-6,9-difluoro-11-hydroxy-16-methyl-pregna-1,4-diene-3,20-dione; Dermaflor; Diacort; Diflorasone 17,21-Diacetate; Difulal; Florone; Maxiflor; Psorcon; Soriflor

登记号

• CAS号: 2557-49-5; 33564-31-7
• EC号: 251-575-1
• MDL号: MFCD00079159
• PubChem SID: 160963571; 24894203
• PubChem CID: 71414

理论计算性质

JChem

• Acid pKa: 13.553008
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 2.2241013
• LogD (pH = 7.4): 2.2241008
• Log P: 2.2241013
• 摩尔折射率: 120.6193 cm^3
• 极化性: 47.113922 Å^3
• 极化表面积: 106.97 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.85
• LOG S: -4.63
• 溶解度: 1.16e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol
• 外观: White Solid
• 熔点: 222-224°C
• 疏水性(logP): 2.1

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: TU3722000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22-40
• 安全公开号: 22-36
• GHS危险品标识: GHS07; GHS08
• GHS警示词: Warning
• GHS危险声明: H312-H332-H351
• GHS警示性声明: P280
• 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

产品相关信息

• 级别: analytical standard, for drug analysis

详细说明

MP Biomedicals - 02157696

(6α,9-Difluoro-11β,17,21-trihydroxy-
16β-methyl-pregna-1,4-diene-
3,20-dione 17,21-diacetate)

DrugBank - DB00223

• Drug Groups: approved
• Description: Diflorasone is a topical corticosteroid used to treat itching and inflammation of the skin.
• Indication: For relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.
• Pharmacology: 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.
• Toxicity: Topically applied diflorasone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized, primarily in the liver, and then excreted by the kidneys.
• Absorption: Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
• Protein Binding: Bound to plasma proteins in varying degrees.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - D445500

An anti-inflammatory and anti-itching corticosteroid usually present in topical creams.

参考文献

• Dikunets, M., et al.: J. Anal. Chem., 64, 832 (2009)
• Maccaroni, E., et al.: Steroids, 74, 102 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)