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Difluprednate

July 24, 2017
Common Name

Difluprednate Description

Difluprednate is only found in individuals that have used or taken this drug. It is a topical corticosteroid indicated for the treatment of infammation and pain associated with ocliar surgery. It was approved by the the US Food and Drug Administration (FDA) on June 24, 2008.Corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins (lipocortins). It is postliated that these proteins control the biosynthesis of potent mediators of infammation 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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source DurezolKegg Difluprednic acidGenerator DFBAHMDB Difluoroprednisolone butyrate acetateHMDB EpitopicMeSH

Chemical Formlia

C27H34F2O7 Average Molecliar Weight

508.5515 Monoisotopic Molecliar Weight

508.227259852 IUPAC Name

(1R,2S,8S,10S,11S,14R,15S,17S)-14-[2-(acetyloxy)acetyl]-1,8-difluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-14-yl butanoate Traditional Name

difluprednate CAS Registry Number

23674-86-4 SMILES

[H][C@@]12CC[C@](OC(=O)CCC)(C(=O)COC(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C

InChI Identifier

InChI=1S/C27H34F2O7/c1-5-6-23(34)36-26(22(33)14-35-15(2)30)10-8-17-18-12-20(28)19-11-16(31)7-9-24(19,3)27(18,29)21(32)13-25(17,26)4/h7,9,11,17-18,20-21,32H,5-6,8,10,12-14H2,1-4H3/t17-,18-,20-,21-,24-,25-,26-,27-/m0/s1

InChI Key

WYQPLTPSGFELIB-JTQPXKBDSA-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

  • Steroid esters
  • 20-oxosteroids
  • 11-beta-hydroxysteroids
  • 3-oxo delta-1,4-steroids
  • Halogenated steroids
  • Delta-1,4-steroids
  • Alpha-acyloxy ketones
  • Dicarboxylic acids and derivatives
  • Cyclic ketones
  • Cyclic alcohols and derivatives
  • Carboxylic acid esters
  • Secondary alcohols
  • Fluorohydrins
  • Hydrocarbon derivatives
  • Alkyl fluorides
  • Organic oxides
  • Organofluorides

    • Substituents

  • Progestogin-skeleton
  • Steroid ester
  • 20-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • 3-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • 9-halo-steroid
  • 6-halo-steroid
  • Halo-steroid
  • Hydroxysteroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclic ketone
  • Secondary alcohol
  • Fluorohydrin
  • Ketone
  • Halohydrin
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Alkyl fluoride
  • Alkyl halide
  • Aliphatic homopolycyclic compound

    • Molecliar Framework

    Aliphatic homopolycyclic compounds External Descriptors

  • butyrate ester (CHEBI:31485 )
  • corticosteroid hormone (CHEBI:31485 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cell signaling
  • Corticosteroids
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Topical Anti-inflammatory Agent

    • Application

  • Nutrients
  • Pharmaceutical
  • Stabilizers
  • Surfactants and Emlisifiers

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0097 mg/mLALOGPS logP3.28ALOGPS logP3ChemAxon logS-4.7ALOGPS pKa (Strongest Acidic)13.55ChemAxon pKa (Strongest Basic)-3.4ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area106.97 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity125.38 m3·mol-1ChemAxon Polarizability51.46 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 – , positivesplash10-03fs-2791000000-5b24de22e5f9ba4a3025View 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 DB06781

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06781

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06781 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

    391990 KEGG Compound ID

    C12695 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Difluprednate NuGOwiki Link

    HMDB15676 Metagene Link

    HMDB15676 METLIN ID

    Not Available PubChem Compound

    443936 PDB ID

    Not Available ChEBI ID

    775700

    Product: Meisoindigo

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Morton KD, Van de Kar LD, Brownfield MS, Bethea CL: Neuronal cell bodies in the hypothalamic paraventricular nucleus mediate stress-induced renin and corticosterone secretion. Neuroendocrinology. 1989 Jul;50(1):73-80. [PubMed:2666872 ]
    2. Korenfeld MS, Silverstein SM, Cooke DL, Vogel R, Crockett RS: Difluprednate ophthalmic emulsion 0.05% for postoperative inflammation and pain. J Cataract Refract Surg. 2009 Jan;35(1):26-34. doi: 10.1016/j.jcrs.2008.09.024. [PubMed:19101421 ]
    3. Jamal KN, Callanan DG: The role of difluprednate ophthalmic emulsion in clinical practice. Clin Ophthalmol. 2009;3:381-90. Epub 2009 Jun 29. [PubMed:19668594 ]
    4. Epocrates [Link]

    PMID: 2231595

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