(1S,2R,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

• ChemBase编号: 1200
• 分子式: C22H29FO5
• 平均质量: 392.4610632
• 单一同位素质量: 392.19990225
• SMILES: F[C@H]1C[C@H]2[C@H]3[C@@]([C@](O)([C@@H](C3)C)C(=O)CO)(C[C@H](O)[C@@H]2[C@@]2(C1=CC(=O)C=C2)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C22H29FO5/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-20(15,2)19(13)17(26)9-21(14,3)22(11,28)18(27)10-24/h4-5,7,11,13-14,16-17,19,24,26,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19-,20+,21+,22+/m1/s1
• InChIKey: MKPDWECBUAZOHP-AFYJWTTESA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC传统名: paramethasone
• 商标名: Haldrone
• 别名: Paramethasone

登记号

• CAS号: 53-33-8
• PubChem SID: 160964662; 46504651
• PubChem CID: 5875

理论计算性质

JChem

• Acid pKa: 12.448742
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 1.2982434
• LogD (pH = 7.4): 1.2982396
• Log P: 1.2982434
• 摩尔折射率: 102.7883 cm^3
• 极化性: 39.61838 Å^3
• 极化表面积: 94.83 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: 1.51
• LOG S: -3.43
• 溶解度: 1.45e-01 g/l

详细说明

DrugBank - DB01384

• Drug Groups: approved
• Description: A glucocorticoid with the general properties of corticosteroids. It has been used by mouth in the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p737)
• Indication: For the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone.
• Pharmacology: Paramethasone is a glucocorticoid with the general properties of corticosteroids. Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger a variety of important cardiovascular, metabolic, immunologic and homeostatic effects. Glucocorticoids are distinguished from mineralocorticoids and sex steroids by having different receptors, target cells, and effects. Technically, the term corticosteroid refers to both glucocorticoids and mineralocorticoids, but is often used as a synonym for glucocorticoid. Glucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.
• Toxicity: Side effects include inhibition of bone formation, suppression of calcium absorption delayed wound healing, immune suppression, and hyperglycemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Protein Binding: 80%
• 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