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

• ChemBase编号: 473
• 分子式: C24H30F2O6
• 平均质量: 452.4882064
• 单一同位素质量: 452.20104512
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C
• Canonical SMILES: 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/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
• InChIKey: FEBLZLNTKCEFIT-VSXGLTOVSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one; (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one; (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0?,?.0?,?.0??,??]icosa-14,17-dien-16-one
• IUPAC传统名: synalar
• 商标名: Coriphate; Derma-smoothe/fs; Dermalar; Flucinar; Flucort; Fluocet; Fluonid; Fluotrex; Fluovitif; Flupollon; FS Shampoo; Jellin; Localyn; Localyn Syntex; Neo-Synalar; Omniderm; Percutina; Radiocin; Retisert; Sinalar; Synalar; Synalar-HP; Synamol; Synandone; Synandrone; Synemol; Synotic; Synsac; Tefunote; Medidur
• 别名: 6α,9α-二氟-11β,16α,17α,21-四羟基-1,4-妊娠双烯-3,20-二酮; 6α,9α-二氟-16α-羟基泼尼松龙16,17-缩丙酮; 6α-氟代曲安奈德; 仙乃乐; 醋酸肤轻松; 醋酸氟轻松; Fluocinolonacetonidum; Fluocinolone acetonide [DCIT]; Fluocinoloni acetonidum [INN-Latin]; flucinolone; Fluocinolone Acetonide; 6α,9α-Difluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione; 6α,9α-Difluoro-16α-hydroxyprednisolone 16,17-acetonide; 6α-Fluorotriamcinolone acetonide; Fluocinolone acetonide; (6α,11β,16α)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; Fluonid; Fluzon; Radiocin; NSC 92339; Synsac; 6α-Fluorotriamcinolone acetonide; Sinalar; Synandone; 6α,9α-Difluoro-11β,16α,17α,21-tetrahydroxy-1,4-pregnadiene-3,20-dione; 6α,9α-Difluoro-16α-hydroxyprednisolone 16,17-acetonide

登记号

• CAS号: 67-73-2
• EC号: 200-668-5
• MDL号: MFCD00010525
• PubChem SID: 24894978; 160963936; 46506244
• PubChem CID: 6215

理论计算性质

JChem

• Acid pKa: 13.351801
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 1.6043986
• LogD (pH = 7.4): 1.6043981
• Log P: 1.6043986
• 摩尔折射率: 111.4132 cm^3
• 极化性: 43.155457 Å^3
• 极化表面积: 93.06 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.47
• LOG S: -3.92
• 溶解度: 5.47e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; DMSO; Methanol
• 外观: White Solid
• 熔点: 265-266°C; 267-269 °C(lit.); 267-269°C
• 比旋光度: [α]25/D +98°, c = 1 in chloroform
• 疏水性(logP): 2.48 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: TU3830000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98%; 97%
• 级别: analytical standard, for drug analysis
• 包装: 100 mg of vial
• Empirical Formula (Hill Notation): C24H30F2O6
• 分类: Derivatives & analogs of Natural Compounds

详细说明

MP Biomedicals - 02151131

Crystals from acetone and hexane.
mp 265-266°C

DrugBank - DB00591

• Drug Groups: approved; investigational
• Description: A glucocorticoid derivative used topically in the treatment of various skin disorders. It is usually employed as a cream, gel, lotion, or ointment. It has also been used topically in the treatment of inflammatory eye, ear, and nose disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732). It is also being investigatied by pSivida and Alimera, under the brand name Medidur, as a sustained release intraocular implant for the treatment of diabetic macular edema.
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also for the treatment of chronic non-infectious uveitis affecting the posterior segment of the eye (Retisert).
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
• Absorption: Rapidly absorbed (15 minutes)
• Half Life: 1.3-1.7 hours
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
• References: Goldstein DA, Godfrey DG, Hall A, Callanan DG, Jaffe GJ, Pearson PA, Usner DW, Comstock TL: Intraocular pressure in patients with uveitis treated with fluocinolone acetonide implants. Arch Ophthalmol. 2007 Nov;125(11):1478-85. Epub 2007 Oct 8. [Pubmed] ; Brumm MV, Nguyen QD: Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. Int J Nanomedicine. 2007;2(1):55-64. [Pubmed] ; Jaffe GJ, Yang CH, Guo H, Denny JP, Lima C, Ashton P: Safety and pharmacokinetics of an intraocular fluocinolone acetonide sustained delivery device. Invest Ophthalmol Vis Sci. 2000 Oct;41(11):3569-75. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - F455800

Glucocorticoid; anti-inflammatory.

参考文献

• Goldstein DA, Godfrey DG, Hall A, Callanan DG, Jaffe GJ, Pearson PA, Usner DW, Comstock TL: Intraocular pressure in patients with uveitis treated with fluocinolone acetonide implants. Arch Ophthalmol. 2007 Nov;125(11):1478-85. Epub 2007 Oct 8. Pubmed
• Brumm MV, Nguyen QD: Fluocinolone acetonide intravitreal sustained release device--a new addition to the armamentarium of uveitic management. Int J Nanomedicine. 2007;2(1):55-64. Pubmed
• Jaffe GJ, Yang CH, Guo H, Denny JP, Lima C, Ashton P: Safety and pharmacokinetics of an intraocular fluocinolone acetonide sustained delivery device. Invest Ophthalmol Vis Sci. 2000 Oct;41(11):3569-75. Pubmed
• Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964)
• Emerson, M.V., et al.: BioDrugs, 21, 245 (1964)