2-{14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl}-2-oxoethyl 2-(diethylamino)acetate

• ChemBase编号: 649
• 分子式: C27H41NO6
• 平均质量: 475.61754
• 单一同位素质量: 475.29338804
• SMILES: OC1(C2(C(C3C(C4(C(=CC(=O)CC4)CC3)C)C(O)C2)CC1)C)C(=O)COC(=O)CN(CC)CC
• Canonical SMILES: CCN(CC(=O)OCC(=O)C1(O)CCC2C1(C)CC(O)C1C2CCC2=CC(=O)CCC12C)CC
• InChI: InChI=1S/C27H41NO6/c1-5-28(6-2)15-23(32)34-16-22(31)27(33)12-10-20-19-8-7-17-13-18(29)9-11-25(17,3)24(19)21(30)14-26(20,27)4/h13,19-21,24,30,33H,5-12,14-16H2,1-4H3
• InChIKey: FWFVLWGEFDIZMJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-{14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl}-2-oxoethyl 2-(diethylamino)acetate
• IUPAC传统名: hydrocortamate
• 商标名: Hydrocortamate Hydrochloride; Magnacort; Ulcort
• 别名: Hydrocortamate

登记号

• CAS号: 76-47-1
• PubChem SID: 160964112
• PubChem CID: 408334

理论计算性质

JChem

• Acid pKa: 12.607479
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 1.3416194
• LogD (pH = 7.4): 2.2769167
• Log P: 2.3214061
• 摩尔折射率: 129.4777 cm^3
• 极化性: 51.001488 Å^3
• 极化表面积: 104.14 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.82
• LOG S: -3.75
• 溶解度: 8.55e-02 g/l

分子性质

理化性质

• 疏水性(logP): 1.2

详细说明

DrugBank - DB00769

• Drug Groups: approved
• Description: Hydrocortamate is a synthetic glucocorticoid used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. 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.
• Indication: Used topically as an antiinflammatory in the treatment of steroid-responsive dermatoses
• Pharmacology: Hydrocortamate is a synthetic glucocorticoid used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. 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 burning, itching, irritation, dryness, folliculitis, hypertrichosis, acneiform eruptions, hypopigmentation, perioral dermatitis, allergic contact dermatitis, maceration of the skin, secondary infection, skin atrophy, striae, miliaria.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic via CYP3A4