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Methylprednisolone

July 24, 2017
Common Name

Methylprednisolone Description

Methylprednisolone is only found in individuals that have used or taken this drug. It is a prednisolone derivative with similar anti-inflammatory action. [PubChem]Unbound glucocorticoids cross cell membranes and bind with high affinity to specific cytoplasmic receptors, modifying transcription and protein synthesis. By this mechanism, glucocorticoids can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (6alpha,11beta)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dioneChEBI 1-dehydro-6alpha-MethylhydrocortisoneChEBI 6alpha-Methyl-11beta,17alpha,21-triol-1,4-pregnadiene-3,20-dioneChEBI Delta(1)-6alpha-MethylhydrocortisoneChEBI MedrateChEBI MedrolChEBI MedroneChEBI MethylprednisolonChEBI MethylprednisolonumChEBI MetilprednisolonaChEBI SolometChEBI UrbasonChEBI (6a,11b)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dioneGenerator (6α,11β)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dioneGenerator 1-dehydro-6a-MethylhydrocortisoneGenerator 1-dehydro-6α-methylhydrocortisoneGenerator 6a-Methyl-11b,17a,21-triol-1,4-pregnadiene-3,20-dioneGenerator 6α-methyl-11β,17α,21-triol-1,4-pregnadiene-3,20-dioneGenerator delta(1)-6a-MethylhydrocortisoneGenerator δ(1)-6α-methylhydrocortisoneGenerator Medric acidGenerator δ(1)-6a-methylhydrocortisoneGenerator 6alpha-MethylprednisoloneHMDB MethyleneprednisoloneHMDB MetilprednisoloneHMDB 6 MethylprednisoloneMeSH 6-MethylprednisoloneMeSH MetipredMeSH

Chemical Formlia

C22H30O5 Average Molecliar Weight

374.4706 Monoisotopic Molecliar Weight

374.20932407 IUPAC Name

(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one Traditional Name

methylprednisolone CAS Registry Number

83-43-2 SMILES

[H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1

InChI Key

VHRSUDSXCMQTMA-PJHHCJLFSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. Kingdom

Organic compounds Super Class

Lipids and lipid-like moleclies Class

Steroids and steroid derivatives Sub Class

Hydroxysteroids Direct Parent

21-hydroxysteroids Alternative Parents

  • Gluco/mineralocorticoids, progestogins and derivatives
  • 20-oxosteroids
  • 3-oxo delta-1,4-steroids
  • 17-hydroxysteroids
  • 11-beta-hydroxysteroids
  • Delta-1,4-steroids
  • Tertiary alcohols
  • Alpha-hydroxy ketones
  • Secondary alcohols
  • Cyclic ketones
  • Cyclic alcohols and derivatives
  • Primary alcohols
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Progestogin-skeleton
  • 21-hydroxysteroid
  • 20-oxosteroid
  • Pregnane-skeleton
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 11-hydroxysteroid
  • 17-hydroxysteroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Tertiary alcohol
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Cyclic ketone
  • Primary alcohol
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • 6-methylprednisolone (CHEBI:6888 )
  • C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030178 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic Agents
  • Anti-inflammatory Agents
  • Antiemetics
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Glucocorticoids
  • Membrane integrity/stability
  • Neuroprotective Agents

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point232.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.09e-01 g/LNot Available LogP1.5Not Available

    Predicted Properties

    Property Value Source Water Solubility0.11 mg/mLALOGPS logP2.06ALOGPS logP1.56ChemAxon logS-3.5ALOGPS pKa (Strongest Acidic)12.58ChemAxon pKa (Strongest Basic)-2.9ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area94.83 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity103.04 m3·mol-1ChemAxon Polarizability40.84 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 – LC-ESI-QTOF , positivesplash10-0a6r-0019000000-3a4955cf7cc34e1e8d0fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0k9i-0696000000-003c4527b983cf71aefdView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-01p9-0980000000-e5097669b38e84057a0fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-01p9-0960000000-ef914702163187cc80afView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-06y9-0940000000-54b01b6c04c68be3f1b3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-0009000000-3fe2869617af3697e2edView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-0009000000-8ad4f169606968256614View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0f79-0895000000-29d1cbf49bb2b32c5a98View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-01p9-0940000000-baa402ac94c228229ea2View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-01p9-0910000000-5cf9fb219d798a9316f4View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4r-0910000000-a2d2af7f573229dc3147View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0006-2900000000-a01d5bfe926dc48e6e4cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-0019000000-11519ee9583104c00505View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0gw0-0974000000-af5d4ebce055ce6efb23View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-01p9-0960000000-22e2342fcec2bf1cd833View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-01p9-0920000000-63759535c53af1efb13fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0c09-1900000000-a48c07db31cf27cf0381View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-05tp-2900000000-b802f5e17b69cd6c707fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT , positivesplash10-0a4i-0009000000-0e0cc8bfc7721357c5cfView 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 DB00959

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00959

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00959 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

    6485 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Methylprednisolone NuGOwiki Link

    HMDB15094 Metagene Link

    HMDB15094 METLIN ID

    Not Available PubChem Compound

    6741 PDB ID

    Not Available ChEBI ID

    6888

    Product: Eltoprazine (hydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Sloka JS, Stefanelli M: The mechanism of action of methylprednisolone in the treatment of multiple sclerosis. Mult Scler. 2005 Aug;11(4):425-32. [PubMed:16042225 ]

    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 ]

    Transporters

    General function:
    Involved in ATP binding
    Specific function:
    Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
    Gene Name:
    ABCB1
    Uniprot ID:
    P08183
    Molecular weight:
    141477.3
    References
    1. Oka A, Oda M, Saitoh H, Nakayama A, Takada M, Aungst BJ: Secretory transport of methylprednisolone possibly mediated by P-glycoprotein in Caco-2 cells. Biol Pharm Bull. 2002 Mar;25(3):393-6. [PubMed:11913542 ]
    2. Troutman MD, Thakker DR: Novel experimental parameters to quantify the modulation of absorptive and secretory transport of compounds by P-glycoprotein in cell culture models of intestinal epithelium. Pharm Res. 2003 Aug;20(8):1210-24. [PubMed:12948019 ]
    3. Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. [PubMed:14661924 ]

    PMID: 26508837

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