(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

• ChemBase编号: 724
• 分子式: C24H33FO6
• 平均质量: 436.5136232
• 单一同位素质量: 436.226117
• SMILES: F[C@H]1C[C@H]2[C@H]3[C@@]([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)(C[C@H](O)[C@@H]2[C@@]2(C1=CC(=O)CC2)C)C
• Canonical SMILES: OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1C[C@@H](C1=CC(=O)CC[C@]21C)F)(C)C
• InChI: InChI=1S/C24H33FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h7,13-14,16-17,19-20,26,28H,5-6,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1
• InChIKey: POPFMWWJOGLOIF-XWCQMRHXSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-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]icos-17-en-16-one; (1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-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}]icos-17-en-16-one
• IUPAC传统名: flurandrenolide
• 商标名: Alondra-F; Cordran; Drenison; Drocort; Haelan; Haldrone-F; Sermaka
• 别名: (6α,11β,16α)-6-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione; 6α-Fluoro-11β,21-dihydroxy-16α,17α-(isopropylidenedioxy)pregn-4-ene-3,20-dione; 6α-Fluoro-16α-hydroxyhydrocortisone 16,17-Acetonide; Alondra F; Cordran; Drenison; Drocort; Fluadrenolone; Fluoroandrenolone acetonide; Haelan; Haldrone F; L 33379; Sermaka; Fludroxycortidum [INN-Latin]; Fludroxicortida [INN-Spanish]; Fludrossicortide [DCIT]; Flurandrenolone; Flurandrenolone acetonide; Fluorandrenolone acetonide; Fluorandrenolone; Fludroxycortide; Fludroxicortidum; Floudroxycortide; Flurandrenolide

登记号

• CAS号: 1524-88-5
• PubChem SID: 46505159; 160964187
• PubChem CID: 15209

理论计算性质

JChem

• Acid pKa: 13.73489
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 1.5629681
• LogD (pH = 7.4): 1.5629679
• Log P: 1.5629681
• 摩尔折射率: 110.7919 cm^3
• 极化性: 43.61583 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: 2.02
• LOG S: -3.88
• 溶解度: 5.78e-02 g/l

分子性质

理化性质

• 溶解度: Insoluble
• 疏水性(logP): 0.6

详细说明

DrugBank - DB00846

• Drug Groups: approved
• Description: A corticosteroid used topically in the treatment of various skin disorders. It is usually employed as a cream or an ointment, and is also used as a polyethylene tape with an adhesive. (From Martindale, The Extra Pharmacopoeia, 30th ed, p733)
• Indication: For relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses, particularly dry, scaling localized lesions
• Pharmacology: Flurandrenolide is primarily effective because of its anti-inflammatory, antipruritic, and vasoconstrictive actions.
• Toxicity: Systemic absorption of topical corticosteroids has produced reversible hypothalamic-pituitary- adrenal (HPA) axis suppression, manifestations of Cushing's syndrome, hyperglycemia, and glucosuria in some patients
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic
• Absorption: Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to those of systemically administered corticosteroids
• Protein Binding: Corticosteroids are bound to plasma proteins in varying degrees.
• Elimination: Topical corticosteroids can be absorbed from normal intact skin. They are metabolized primarily in the liver and then excreted in the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - F598650

Glucocorticoid; antipsoriatic.

参考文献

• Pearlman, R., et al.: Int. J. Pharm., 18, 53 (1984)
• Neufeld, E., et al.: J. Chromatogr., 718, 273 (1984)