2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethyl acetate

• ChemBase编号: 1198
• 分子式: C23H30O6
• 平均质量: 402.4807
• 单一同位素质量: 402.20423868
• SMILES: O[C@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)C(=O)C2)CC1)C)C(=O)COC(=O)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)CC(=O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
• InChI: InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-17,20,28H,4-9,11-12H2,1-3H3/t16-,17-,20+,21-,22-,23-/m0/s1
• InChIKey: ITRJWOMZKQRYTA-RFZYENFJSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl]-2-oxoethyl acetate; 2-[(1S,2R,10S,11S,14R,15S)-14-hydroxy-2,15-dimethyl-5,17-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethyl acetate
• IUPAC传统名: cortisone acetate
• 别名: Artriona; Biocort Acetate; Cortadren; Incortin; NSC 49420; Scheroson; Cortisone acetate; 17α,21-Dihydroxy-4-pregnene-3,11,20-trione 21-acetate; 21-Acetoxy-4-pregnen-17α-ol-3,11,20-trione; 4-Pregnene-17α,21-diol-3,11,20-trione 21-acetate; Cortisone 21-acetate; 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate; 17,21-Dihydroxypregn-4-ene-3,11,20-trione 21 acetate; Cortone 21-Acetate; 21-Acetoxy-17α-hydroxy-3,11,20-triketopregnene-4; Cortone Acetate; 21-Acetoxy-17α-hydroxypregn-4-ene-3,11,20-trione; Irisone acetate; 4-Pregnene-17a,21-diol-3,11,20-trione 21-Acetate; Adreson; Compound E Acetate; Corlin; Cortelan; Cortistab; Cortisyl; Cortisyl Artriona; Ricortex

登记号

• CAS号: 50-04-4
• EC号: 200-006-5
• MDL号: MFCD00003609
• Beilstein号: 2067543
• PubChem SID: 24278306; 160964660; 46508852
• PubChem CID: 5745

理论计算性质

JChem

• 极化性: 41.58911 Å^3
• 极化表面积: 97.74 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true
• Acid pKa: 12.601159
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 2.1018062
• LogD (pH = 7.4): 2.1018033
• Log P: 2.1018062
• 摩尔折射率: 105.6263 cm^3

ALOGPS 2.1

• 溶解度: 2.78e-02 g/l
• Log P: 2.35
• LOG S: -4.16

分子性质

理化性质

• 溶解度: 0.02 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Chloroform; Methanol
• 外观: Off-White Solid
• 熔点: 237-240 °C(lit.); 241-244°C
• 疏水性(logP): 2.10 [HANSCH,C ET AL. (1995)]

安全信息

• 保存条件: -20°C; Refrigerator
• RTECS编号: GM9140000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... FNTA(2339)

产品相关信息

• 纯度: ≥99%
• 成盐信息: Free Base
• 分类: Derivatives & analogs of Natural Compounds

详细说明

MP Biomedicals - 05203900

MP Biomedicals Rare Chemical collection

DrugBank - DB01380

• Drug Groups: approved
• Description: Cortisone acetate is a steroid hormone that has both glucocoriticoid and mineral corticoid activities. Corticosteroids are used to provide relief for inflamed areas of the body. They lessen swelling, redness, itching, and allergic reactions. They are often used as part of the treatment for a number of different diseases, such as severe allergies or skin problems, asthma, or arthritis. Endogenous glucocorticoids and some synthetic corticoids have high affinity to the protein transcortin (also called CBG, corticosteroid-binding protein), whereas all of them bind albumin. Glucocorticoids also bind to the cytosolic glucocorticoid receptor.
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). It is also used to treat many immune and allergic disorders.
• Pharmacology: As a glucocorticoid agent, cortisone acetate changes genetic transcription levels causing varied metabolic effects and a modified immune response to varied stimuli. lucocorticoids 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 and hyperglycemia.
• Affected Organisms: Humans and other mammals
• 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; Drugs.com

Selleck Chemicals - S2559

Research Area: Immunology
Biological Activity:
Cortisone acetate (Cortone) is an acetate salt form of cortisone that is a steroid hormone and a glucocorticoid. Cortisone acetate (Cortone) is used to treat a variety of ailments. Cortisone acetate (Cortone) suppresses the immune system, thus reducing inflammation and attendant pain and swelling at the site of the injury. Cortisone and adrenaline are the main hormones released by the body as a reaction to stress. They elevate blood pressure and prepare the body for a fight or flight response. Cortisone acetate (Cortone) may also be used to deliberately suppress immune response in persons with autoimmune diseases or following an organ transplant to prevent transplant rejection. The suppression of the immune system may also be important in the treatment of inflammatory conditions such as severe IgE-mediated allergies. [1]

Toronto Research Chemicals - C696510

Cortisone Acetate is a glucocorticoid. Cortisone Acetate is an antiinflammatory agent. Cortisone Acetate is bioavailable and readily converted to the therapeutically active form, Hydrocotisone (H714615).

参考文献

• http://en.wikipedia.org/wiki/Cortisone
• Colburn, W. et al.: J. Clin. Pharmacol., 20, 428 (1980)
• Bailey, J.M. et al.: Atherosclerosis, 17, 515 (1980)