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...

General Information

Structure

Molecular Formula

C₂₃H₃₀O₆

Molecular Mass

402.4807

Exact Mass

402.20423868

Charge

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

Calculated Properties

JChem

Acid pKa

12.601159

H Acceptors

H Donor

LogD (pH = 5.5)

2.1018062

LogD (pH = 7.4)

2.1018033

Log P

2.1018062

Molar Refractivity

105.6263

Polarizability

41.58911

Polar Surface Area

97.74

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

2.35

LOG S

-4.16

Solubility (Water)

2.78e-02 g/l

Data Source

Names and Identifiers

IUPAC name

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 Traditional name

cortisone acetate

Synonyms

Cortisone acetateNSC 49420ArtrionaIncortinBiocort AcetateCortadrenScheroson4-Pregnene-17α,21-diol-3,11,20-trione 21-acetateCortisone 21-acetate17α,21-Dihydroxy-4-pregnene-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 acetateCompound E AcetateIrisone acetateCortisylCortisyl Artriona4-Pregnene-17a,21-diol-3,11,20-trione 21-Acetate21-Acetoxy-17α-hydroxy-3,11,20-triketopregnene-421-Acetoxy-17α-hydroxypregn-4-ene-3,11,20-trioneCortistabCorlinRicortexAdresonCortone 21-AcetateCortelan17,21-Dihydroxypregn-4-ene-3,11,20-trione 21 acetateCortone Acetate

Names and Identifiers

Registration numbers

CAS Number

50-04-4

PubChem SID

4650885224278306160964660

PubChem CID

Beilstein Number

MDL Number

EC Number

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

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

Solubility

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

Methanol

Chloroform

Melting Point

237-240 °C(lit.)

241-244°C

Apperance

Off-White Solid

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Purity

≥99%

Classification

Derivatives & analogs of Natural Compounds

Safety Information

Storage Condition

-20°C

Refrigerator

MSDS Link

Download link

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

GM9140000

Pharmacology Properties

Gene Information

human ... FNTA(2339)

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

IUPAC Traditional name

cortisone acetate

Synonyms

Registration numbers

CAS Number

50-04-4

PubChem SID

4650885224278306160964660

PubChem CID

Beilstein Number

MDL Number

EC Number

References

PubChem Literature

From Data Sources

• 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)

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

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

Solubility

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

Methanol

Chloroform

Melting Point

237-240 °C(lit.)

241-244°C

Apperance

Off-White Solid

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Purity

≥99%

Classification

Derivatives & analogs of Natural Compounds

Safety Information

Storage Condition

-20°C

Refrigerator

MSDS Link

Download link

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

GM9140000

Pharmacology Properties

Gene Information

human ... FNTA(2339)

Molecule Details

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]

Molecule

ID:1198