Difluprednate (CED0009630)

Record Information
Version1.0
Creation Date2016-05-22 05:56:31 UTC
Update Date2026-08-22 07:35:29 UTC
Accession NumberCHEM019241
Identification
Common NameDifluprednate
ClassSmall Molecule
Description
Difluprednate belongs to the pregnane steroids, a subclass of steroids and steroid derivatives within the organic compounds. With an average molecular weight of 508.55 g/mol, Difluprednate is a heavy molecule. It has the chemical formula C27H34F2O7. The compound is recorded as being found in or released from six sources. These include corticosteroids and antiinflammatory agents within healthcare, pharmaceuticals, and veterinary products, as well as the treatment of hops and processing meats in food, food processing, and cookware. Additionally, it is associated with thin magnetic films in electrical and electronic equipment, and non electric simulated smoking devices in household cleaning and consumer products. The recorded route of exposure for this compound is ophthalmic. Difluprednate interacts with two recorded protein targets. It acts as an agonist of the glucocorticoid receptor (NR3C1) and also targets annexin A1 (ANXA1).
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
DurezolKegg
Difluprednic acidGenerator
DFBAHMDB
Difluoroprednisolone butyrate acetateHMDB
EpitopicHMDB
(6alpha,11beta)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dioneHMDB
(6Α,11β)-21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dioneHMDB
6alpha,9-Difluoroprednisolone 21-acetate 17-butyrateHMDB
6alpha,9alpha-Difluoroprednisolone 21-acetate 17-butyrateHMDB
6Α,9-difluoroprednisolone 21-acetate 17-butyrateHMDB
6Α,9α-difluoroprednisolone 21-acetate 17-butyrateHMDB
DifluprednateHMDB
Chemical FormulaC27H34F2O7
Average Molecular Mass508.552 g/mol
Monoisotopic Mass508.227 g/mol
CAS Registry Number23674-86-4
IUPAC Name(1R,2S,8S,10S,11S,14R,15S,17S)-14-[2-(acetyloxy)acetyl]-1,8-difluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl butanoate
Traditional Name(1R,2S,8S,10S,11S,14R,15S,17S)-14-[2-(acetyloxy)acetyl]-1,8-difluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl butanoate
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 IdentifierInChI=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 KeyWYQPLTPSGFELIB-JTQPXKBDSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPregnane steroids
Direct ParentGluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0097 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity125.38 m³·mol⁻¹ChemAxon
Polarizability51.45 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-000l-9552400000-33149d34148cf703e294Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-01bc-7109060000-ef2a03a71e2849341fafNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03fs-2791000000-5b24de22e5f9ba4a3025Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fu-3000920000-b801ea0df202926edf9dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9016800000-c3f8033bb4780f75f100Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002u-5094100000-e2ed059be58e5c296d46Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9000430000-b82076e5cf29c0fc4925Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9001200000-9712484230dd49ea0ca4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9001000000-b1b809bc178ec908ff1aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1001960000-b5a5d1007ea1eb1a077bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-2013920000-ac8bcafa6e08ca559470Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fkd-2359200000-a40556c9d6dda3e763ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-9102130000-1c706b05a05d8f13faf8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-9006000000-b8db7d4e3e345832eed1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05my-9004000000-6def3190656c1f1685b2Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
589.0Log mg/kg[330:1000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
309CorticosteroidsHealthcare, pharmaceuticals & veterinary productsNot Available
396Antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
552Processing MeatsFood, food processing & cookwareNot Available
553Treatment Of HopsFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.700643
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)6.69503
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.233548
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)145.578
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)25.6124
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)89.4488
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)33.1638
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)104.396
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)241.644
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)1.86838
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)512.793
Protein kinase C epsilon type structureClick to view 3D structureProtein kinase C epsilon typeQ02156HumansPredicted (SEA)776.312
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)826.914
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)2354.63
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)6192.21
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)4642.23
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)4494.16
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)4762.82
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)4774.88
Click to view 3D structureGlucocorticoid receptorP06537Mus musculusPredicted (SEA)11.4438
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansPredicted (SEA)905.62
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)11.8331
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)3.97031
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)16.6597
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)14.4021
Concentrations
Not Available
External Links
DrugBank IDDB06781
HMDB IDHMDB0015676
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDifluprednate
Chemspider ID391990
ChEBI IDNot Available
PubChem Compound ID443936
Kegg Compound IDC12695
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
3. Jamal KN, Callanan DG: The role of difluprednate ophthalmic emulsion in clinical practice. Clin Ophthalmol. 2009;3:381-90. Epub 2009 Jun 29.
4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
8. The lipid handbook with CD-ROM
9. Epocrates: https://online.epocrates.com/u/10a4844/Durezol