CAS 50-04-4|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|cortisone acetate|Cortisone acetate|NSC 49420|Art...

基本信息

化学结构

分子式

C₂₃H₃₀O₆

分子量

402.4807

精确质量

402.20423868

电荷

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

Canonic 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

Isomeric 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

计算属性

JChem

Acid pKa

12.601159

质子受体

质子供体

LogD (pH = 5.5)

2.1018062

LogD (pH = 7.4)

2.1018033

Log P

2.1018062

摩尔折射率

105.6263

极化性

41.58911

极化表面积

97.74

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

2.35

LOG S

-4.16

溶解度

2.78e-02 g/l

数据来源

名称和标识

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[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]-2-oxoethyl acetate

IUPAC传统名

cortisone acetate

别名

Cortisone acetateArtrionaIncortinScherosonNSC 49420Biocort AcetateCortadrenCortisone 21-acetate17α,21-Dihydroxy-4-pregnene-3,11,20-trione 21-acetate4-Pregnene-17α,21-diol-3,11,20-trione 21-acetate21-Acetoxy-4-pregnen-17α-ol-3,11,20-trione2-((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 acetateIrisone acetateCortisyl Artriona21-Acetoxy-17α-hydroxypregn-4-ene-3,11,20-trione21-Acetoxy-17α-hydroxy-3,11,20-triketopregnene-44-Pregnene-17a,21-diol-3,11,20-trione 21-AcetateCortisylCompound E AcetateCortelanCortone 21-AcetateCortistabCortone AcetateAdreson17,21-Dihydroxypregn-4-ene-3,11,20-trione 21 acetateCorlinRicortex

名称和标识

数据登录号

CAS号

50-04-4

PubChem SID

4650885224278306160964660

PubChem CID

Beilstein号

MDL号

EC号

数据登录号

化合物性质

理化性质

溶解度

0.02 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Chloroform

Methanol

疏水性(logP)

2.10 [HANSCH,C ET AL. (1995)]

熔点

237-240 °C(lit.)

241-244°C

Off-White Solid

药理学性质

human ... FNTA(2339)

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

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描述信息

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]

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]

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Cortisone

• Bailey, J.M. et al.: Atherosclerosis, 17, 515 (1980)

• Colburn, W. et al.: J. Clin. Pharmacol., 20, 428 (1980)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

IUPAC传统名

cortisone acetate

别名

数据登录号

CAS号

50-04-4

PubChem SID

4650885224278306160964660

PubChem CID

Beilstein号

MDL号

EC号

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Cortisone

• Bailey, J.M. et al.: Atherosclerosis, 17, 515 (1980)

• Colburn, W. et al.: J. Clin. Pharmacol., 20, 428 (1980)

生物活性

PubChem BioAssay

化合物性质

理化性质

溶解度

0.02 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Chloroform

Methanol

疏水性(logP)

2.10 [HANSCH,C ET AL. (1995)]

熔点

237-240 °C(lit.)

241-244°C

Off-White Solid

药理学性质

human ... FNTA(2339)

描述信息

Selleck Chemicals

S2559

DrugBank

DB01380

Drug Groups

approved

Description

Indication

Pharmacology

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]

化合物信息

ID:1198