2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl acetate

• ChemBase编号: 919
• 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@@]4(OC(O[C@@H]4C3)(C)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)OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1C[C@@H](C1=CC(=O)C=C[C@]21C)F)F)(C)C
• InChI: InChI=1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1
• InChIKey: WJOHZNCJWYWUJD-IUGZLZTKSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-8-yl]-2-oxoethyl acetate; 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl acetate; 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0?,?.0?,?.0??,??]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
• IUPAC传统名: fluocinonide
• 商标名: Bestasone; Biscosal; Cortalar; Fluzon; Lidex; Lidex E; Metosyn; Straderm; Synalar acetate; Topsymin; Topsyn; Vanos; Fluonex; Lidex-E; Lonide; Lyderm
• 别名: (6α,11β,16α)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; Biscosal; Dermaplus; Flucetonide; Flucinar; Lidex E; Metosyn; NSC 101791; Straderm; Topsym; Topsymin; Topsyn; Topsyne; Vanos; Fluocinolone Acetonide Acetate; Fluonex; Lidex; Lidex-E; Lonide; Lyderm; Fluocinolide acetate; Fluocinolide; Fluocinolone acetonide acetate; Fluocinonide Emulsified Base; Fluocinonide [USAN:BAN:INN:JAN]; Fluocinonido [INN-Spanish]; Fluocinonidum [INN-Latin]; fluocinonide; Fluocinonide; Fluocinomide; FLUOCINOLONE ACETONIDE 21-ACETATE; (6α,11β,16α)-21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; Fluocinonide

登记号

• CAS号: 56-12-7; 356-12-7
• EC号: 206-597-6
• MDL号: MFCD00079302
• PubChem SID: 46504523; 160964382
• PubChem CID: 9642
• ATC码: D07AC08; C05AA11
• CHEMBL: 1501
• Chemspider ID: 9265
• DrugBank ID: DB01047
• KEGG ID: D00325
• 美国药典/FDA物质标识码: 2W4A77YPAN
• 维基百科标题: Fluocinonide
• Medline Plus: a601054

理论计算性质

JChem

• Acid pKa: 13.551528
• 质子受体: 6
• 质子供体: 1
• LogD (pH = 5.5): 2.045524
• LogD (pH = 7.4): 2.0455236
• Log P: 2.045524
• 摩尔折射率: 120.5647 cm^3
• 极化性: 47.012203 Å^3
• 极化表面积: 99.13 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.93
• LOG S: -4.47
• 溶解度: 1.68e-02 g/l

分子性质

理化性质

• 溶解度: 4.74 mg/L; DMSO; DMSO: ≥19 mg/mL; Methanol
• 外观: White Solid; white to tan powder
• 熔点: 296-297°C (dec.)
• 比旋光度: [α]/D +75 to +90°, c = 1 in dichloromethane
• 疏水性(logP): 1.9

安全信息

• 保存条件: -20°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: TU3831000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2811
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): II
• 澳大利亚Hazchem: 2XE
• 危险公开号: R:28
• 安全公开号: S:28-29-36/37/39-45
• 欧盟危险货物分类: T2
• 欧盟危险识别号(EUHIN): 6.1B
• 美国ERG指导号: 154
• 保存温度: 2-8°C

药理学性质

• 给药途径: topical
• 代谢: hepatic
• 法定药品分级: POM (UK); Rx-only (US); S4 (Australia)
• 妊娠期药物分类: C

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C26H32F2O7
• 分类: Derivatives & analogs of Natural Compounds

详细说明

MP Biomedicals - 02158060

(Fluocinomide)

DrugBank - DB01047

• Drug Groups: approved; investigational
• Description: A topical glucocorticoid used in the treatment of eczema. [PubChem]
• Indication: A topical anti-inflammatory product for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Pharmacology: Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. [Wikipedia]
• Toxicity: Side effects may include acne-like eruptions, burning, dryness, excessive hair growth, infection of the skin, irritation, itching, lack of skin color, prickly heat, skin inflammation, skin loss or softening, stretch marks
• Affected Organisms: Humans and other mammals
• Absorption: The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle, the integrity of the epidermal barrier, and the use of occlusive dressings. In general, percutaneous absorption is minimal.
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S2608

Research Area: Inflammation
Biological Activity:
Fluocinonide(Vanos) is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. [1]

Sigma Aldrich - SML0099

Biochem/physiol Actions
Flucinonide is a fluorinated glucocorticid that is used as a topical anti-inflammatory agent. Recently, flucinonide and other fluorinated glucocorticolids were identified as smoothend agonists. Flucinonide induces expression of Gli-reporter luciferase in Shh-LIGHT2 cells.

Toronto Research Chemicals - F455805

Glucocorticoid; anti-inflammatory.

参考文献

• http://en.wikipedia.org/wiki/Fluocinonide
• Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964)
• Brunmair, B., et al.: J. Pharmacol. Exp. Therap., 311, 109 (1964)
• Emerson, M.V., et al.: BioDrugs, 21, 245 (1964)