2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate

• ChemBase编号: 173
• 分子式: C28H35FO7
• 平均质量: 502.5717032
• 单一同位素质量: 502.23668168
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@@]4(OC5(O[C@@H]4C3)CCCC5)C(=O)COC(=O)C)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]12OC3(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1CCC1=CC(=O)C=C[C@]21C)F)CCCC3
• InChI: InChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
• InChIKey: ILKJAFIWWBXGDU-MOGDOJJUSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate; 2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate; 2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0?,?.0?,?.0??,??]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate
• IUPAC传统名: cyclocort; amcinonide
• 商标名: Cyclocort
• 别名: 安西奈德; Amcinonide; Amcinonide; (11β,16α)-21-(Acetyloxy)-16,17-[cyclopentylidenebis(oxy)]-9-fluoro-11-hydroxypregna-1,4-diene-3,20-dione; Amciderm; Amcinonid; Amcinonide; CL 34699; Cyclocort; Penticort; Visderm

登记号

• CAS号: 51022-69-6
• EC号: 256-915-2
• MDL号: MFCD00213379
• PubChem SID: 24890657; 160963636; 46506705
• PubChem CID: 443958

理论计算性质

ALOGPS 2.1

• Log P: 3.16
• LOG S: -4.81
• 溶解度: 7.74e-03 g/l

JChem

• Log P: 3.1952636
• 摩尔折射率: 127.8767 cm^3
• 极化性: 50.165337 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: false
• Acid pKa: 13.633899
• 质子受体: 6
• 质子供体: 1
• LogD (pH = 5.5): 3.1952636
• LogD (pH = 7.4): 3.1952634

分子性质

理化性质

• 疏水性(logP): 2.3

安全信息

• RTECS编号: TU3682500
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 级别: analytical standard, for drug analysis
• Empirical Formula (Hill Notation): C28H35FO7

详细说明

DrugBank - DB00288

• Drug Groups: approved
• Description: Amcinonide is a corticosteroid. [Wikipedia]
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Pharmacology: Amcinonide is a topical corticosteroid. The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. Amcinonide reduces or inhibits the actions of chemicals in the body that cause inflammation, redness, and swelling. The mechanism of anti-inflammatory activity of the topical corticosteroids is unclear. Various laboratory methods, including vasoconstrictor assays, are used to compare and predict potencies and/or clinical efficacies of the topical corticosteroids. There is some evidence to suggest that a recognizable correlation exists between vasoconstrictor potency and therapeutic efficacy in man. When in an ointment form, amcinonide also helps the skin maintain moisture.
• Toxicity: Results from acute toxicity studies do not indicate that any risk of acute intoxication is to be expected following a single dermal application of an overdose (application over a large area under conditions favorable to absorption) or inadvertent oral ingestion.
• Affected Organisms: Humans and other mammals
• Biotransformation: Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
• Absorption: Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.
• 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.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - A576150

Glucocorticoid.

参考文献

• Woodford, R., et al.: Curr. Ther. Res., 26, 301 (1979)