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Cortisone acetate

July 24, 2017
Common Name

Cortisone acetate 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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source CortisylKegg Cortone acetateKegg Cortisone acetic acidGenerator Cortone acetic acidGenerator AdresonMeSH CortisoneMeSH

Chemical Formlia

C23H30O6 Average Molecliar Weight

402.4807 Monoisotopic Molecliar Weight

402.204238692 IUPAC Name

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 Traditional Name

cortisone acetate CAS Registry Number

50-04-4 SMILES

[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)CC(=O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

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

InChI Key

ITRJWOMZKQRYTA-RFZYENFJSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Kingdom

Organic compounds Super Class

Lipids and lipid-like moleclies Class

Steroids and steroid derivatives Sub Class

Pregnane steroids Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives Alternative Parents

  • 20-oxosteroids
  • 3-oxo delta-4-steroids
  • 17-hydroxysteroids
  • 11-oxosteroids
  • Delta-4-steroids
  • Cyclohexenones
  • Alpha-acyloxy ketones
  • Tertiary alcohols
  • Alpha-hydroxy ketones
  • Cyclic alcohols and derivatives
  • Carboxylic acid esters
  • Monocarboxylic acids and derivatives
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Progestogin-skeleton
  • 20-oxosteroid
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • 11-oxosteroid
  • Oxosteroid
  • Delta-4-steroid
  • Cyclohexenone
  • Alpha-acyloxy ketone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • corticosteroid hormone (CHEBI:3897 )
  • C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C08173 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030120 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-inflammatory Agents
  • Cell signaling
  • Corticosteroid
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point222 °CNot Available Boiling PointNot AvailableNot Available Water Solubility2.78e-02 g/LNot Available LogP2.10HANSCH,C ET AL. (1995)

    Predicted Properties

    Property Value Source Water Solubility0.028 mg/mLALOGPS logP2.35ALOGPS logP2.1ChemAxon logS-4.2ALOGPS pKa (Strongest Acidic)12.6ChemAxon pKa (Strongest Basic)-3.8ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area97.74 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity105.63 m3·mol-1ChemAxon Polarizability43.25 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0udi-0643900000-f8c82718aaac7d5f1097View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-03di-2941000000-b0ec70aa310131ced784View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01380

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01380

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01380 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5543 KEGG Compound ID

    C08173 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cortisone_acetate NuGOwiki Link

    HMDB15459 Metagene Link

    HMDB15459 METLIN ID

    Not Available PubChem Compound

    5745 PDB ID

    Not Available ChEBI ID

    587711

    Product: Azelastine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References Not Available

    Enzymes

    General function:
    Involved in monooxygenase activity
    Specific function:
    Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
    2. Ekins S, Bravi G, Wikel JH, Wrighton SA: Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33. [PubMed:10490933 ]

    PMID: 1970502

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