Posted inUncategorized

Clobetasol

July 24, 2017
Common Name

Clobetasol Description

Clobetasol is only found in individuals that have used or taken this drug. It is a derivative of prednisolone with high glucocorticoid activity and low mineralocorticoid activity. Absorbed through the skin faster than fluocinonide, it is used topically in treatment of psoriasis but may cause marked adrenocortical suppression. [PubChem]The precise mechanism of the antiinflammatory activity of topical steroids in the treatment of steroid-responsive dermatoses, in general, is uncertain. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postliated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Initially, however, clobetasol, like other corticosteroids, bind to the glucocorticoid receptor, which complexes, enteres the cell nucleus and modifies genetic transcription (transrepression/transactivation). Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (11beta,16beta)-21-chloro-9-fluoro-11,17-Dihydroxy-16-methylpregna-1,4-diene-3,20-dioneChEBI ClobetasolumChEBI (11b,16b)-21-chloro-9-fluoro-11,17-Dihydroxy-16-methylpregna-1,4-diene-3,20-dioneGenerator (11β,16β)-21-chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dioneGenerator Clobetasol 17 propionateMeSH Clobetasol 17-propionateMeSH Clobetasol propionateMeSH ClobexMeSH ClofenazonMeSH CormaxMeSH DermovateMeSH EmbelineMeSH Embeline eMeSH OLUXMeSH TemovateMeSH

Chemical Formlia

C22H28ClFO4 Average Molecliar Weight

410.907 Monoisotopic Molecliar Weight

410.166015296 IUPAC Name

(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one Traditional Name

clobetasol CAS Registry Number

25122-46-7 SMILES

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

InChI Identifier

InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1

InChI Key

FCSHDIVRCWTZOX-DVTGEIKXSA-N Chemical Taxonomy Description

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

Chemical entities Super Class

Organic compounds Class

Lipids and lipid-like moleclies Sub Class

Steroids and steroid derivatives Direct Parent

Gluco/mineralocorticoids, progestogins and derivatives Alternative Parents

  • 20-oxosteroids
  • 11-beta-hydroxysteroids
  • 17-hydroxysteroids
  • 3-oxo delta-1,4-steroids
  • Halogenated steroids
  • Delta-1,4-steroids
  • Tertiary alcohols
  • Alpha-hydroxy ketones
  • Alpha-chloroketones
  • Secondary alcohols
  • Fluorohydrins
  • Cyclic ketones
  • Cyclic alcohols and derivatives
  • Alkyl fluorides
  • Alkyl chlorides
  • Hydrocarbon derivatives
  • Organic oxides
  • Organochlorides
  • Organofluorides

    • Substituents

  • Progestogin-skeleton
  • 20-oxosteroid
  • Hydroxysteroid
  • Halo-steroid
  • 9-halo-steroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 17-hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-haloketone
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Tertiary alcohol
  • Alpha-chloroketone
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Halohydrin
  • Ketone
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alkyl halide
  • Alkyl fluoride
  • Organofluoride
  • Organochloride
  • Organohalogen compound
  • Alkyl chloride
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • 11beta-hydroxy steroid (CHEBI:205919 )
  • 17alpha-hydroxy steroid (CHEBI:205919 )
  • glucocorticoid (CHEBI:205919 )
  • 20-oxo steroid (CHEBI:205919 )
  • fluorinated steroid (CHEBI:205919 )
  • 3-oxo-Delta(1),Delta(4)-steroid (CHEBI:205919 )
  • chlorinated steroid (CHEBI:205919 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-inflammatory Agents
  • Cell signaling
  • Corticosteroids, topical
  • Fuel and energy storage
  • Fuel or energy source
  • Glucocorticoids
  • 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 Point195.5 – 197 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.42e-02 g/LNot Available LogP3Not Available

    Predicted Properties

    Property Value Source Water Solubility0.014 mg/mLALOGPS logP2.72ALOGPS logP3.04ChemAxon logS-4.5ALOGPS pKa (Strongest Acidic)12.47ChemAxon pKa (Strongest Basic)-3.4ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area74.6 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity105.54 m3·mol-1ChemAxon Polarizability41.97 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key 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 DB01013

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01013

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01013 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

    4470588 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Clobetasol NuGOwiki Link

    HMDB15148 Metagene Link

    HMDB15148 METLIN ID

    Not Available PubChem Compound

    5311051 PDB ID

    Not Available ChEBI ID

    205919

    Product: THZ2 (Hydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
    Gene Name:
    CYP1A1
    Uniprot ID:
    P04798
    Molecular weight:
    58164.815
    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 ]
    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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
    Gene Name:
    CYP1A2
    Uniprot ID:
    P05177
    Molecular weight:
    58406.915
    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 ]

    PMID: 11226258

    Last updated on