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Identification
NameDiflorasone
Accession NumberDB00223  (APRD00921)
Typesmall molecule
Groupsapproved
Description

Diflorasone is a topical corticosteroid used to treat itching and inflammation of the skin.

Structure
Thumb
Synonyms
SynonymLanguageCode
(6alpha,11beta,16beta)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dioneNot AvailableNot Available
(6α,11β,16β)-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dioneNot AvailableNot Available
DiflorasonaNot AvailableNot Available
DiflorasonumNot AvailableNot Available
Salts
Name/CAS Structure Properties
Diflorasone diacetate
Thumb Not applicable DBSALT000887
Brand names
NameCompany
ApexiConNot Available
FloroneGalderma
Florone ENot Available
MaxiflorNot Available
PsorconNot Available
Brand mixturesNot Available
Categories
CAS number2557-49-5
WeightAverage: 410.4515
Monoisotopic: 410.190480416
Chemical FormulaC22H28F2O5
InChI KeyWXURHACBFYSXBI-XHIJKXOTSA-N
InChI
InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13-,14-,16-,17-,19-,20-,21-,22-/m0/s1
IUPAC Name
(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
SMILES
[H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Ketosteroids; Halogenated Steroids; Iridoids and Derivatives; Cyclohexanols; Tertiary Alcohols; Cyclic Alcohols and Derivatives; Ketones; Fluorohydrins; Polyamines; Enolates; Primary Alcohols; Organofluorides; Alkyl Fluorides; Aldehydes
Substituents3-keto-steroid; 20-keto-steroid; 9-halo-steroid; 6-halo-steroid; 17-hydroxy-steroid; 11-hydroxy-steroid; 11-noriridane monoterpene; monoterpene; cyclohexanol; tertiary alcohol; cyclic alcohol; secondary alcohol; ketone; halohydrin; fluorohydrin; polyamine; enolate; primary alcohol; alcohol; organofluoride; organohalogen; carbonyl group; alkyl halide; alkyl fluoride; aldehyde
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationFor relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.
PharmacodynamicsLike other topical corticosteroids, diflorasone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Diflorasone is a potent topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
Mechanism of actionThe 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 postulated 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.
AbsorptionTopical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
Volume of distributionNot Available
Protein bindingBound to plasma proteins in varying degrees.
Metabolism

Metabolized, primarily in the liver, and then excreted by the kidneys.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityTopically applied diflorasone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9948
Blood Brain Barrier + 0.971
Caco-2 permeable + 0.747
P-glycoprotein substrate Substrate 0.7725
P-glycoprotein inhibitor I Non-inhibitor 0.7629
P-glycoprotein inhibitor II Non-inhibitor 0.9002
Renal organic cation transporter Non-inhibitor 0.8405
CYP450 2C9 substrate Non-substrate 0.8789
CYP450 2D6 substrate Non-substrate 0.9031
CYP450 3A4 substrate Substrate 0.6991
CYP450 1A2 substrate Non-inhibitor 0.9313
CYP450 2C9 substrate Non-inhibitor 0.9254
CYP450 2D6 substrate Non-inhibitor 0.939
CYP450 2C19 substrate Non-inhibitor 0.9234
CYP450 3A4 substrate Non-inhibitor 0.7563
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8979
Ames test Non AMES toxic 0.8509
Carcinogenicity Non-carcinogens 0.9232
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.3293 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9794
hERG inhibition (predictor II) Non-inhibitor 0.6022
Pharmacoeconomics
Manufacturers
  • Altana inc
  • Taro pharmaceuticals usa inc
  • Pharmacia and upjohn co
  • Sanofi aventis us llc
  • Taro pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical
Prices
Unit descriptionCostUnit
Psorcon 0.05% Ointment 60 gm Tube145.75USDtube
Psorcon 0.05% Cream 60 gm Tube137.58USDtube
Diflorasone Diacetate 0.05% Cream 60 gm Tube101.11USDtube
Diflorasone Diacetate 0.05% Ointment 60 gm Tube100.5USDtube
Diflorasone Diacetate 0.05% Cream 30 gm Tube52.81USDtube
Diflorasone Diacetate 0.05% Ointment 30 gm Tube52.29USDtube
Diflorasone Diacetate 0.05% Cream 15 gm Tube38.25USDtube
Diflorasone Diacetate 0.05% Ointment 15 gm Tube38.05USDtube
Psorcon 0.05% cream3.45USDg
Diflorasone 0.05% cream1.5USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP2.1Not Available
Predicted Properties
PropertyValueSource
water solubility8.53e-02 g/lALOGPS
logP1.91ALOGPS
logP1.34ChemAxon
logS-3.7ALOGPS
pKa (strongest acidic)12.42ChemAxon
pKa (strongest basic)-3.3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area94.83ChemAxon
rotatable bond count2ChemAxon
refractivity102.32ChemAxon
polarizability40.95ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Lincoln, F.H., Schneider, W.P. and Spero, G.B.; U.S. Patent 3,557,158; January 19,1971; assigned to The Upjohn Company.
Ayer, D.E., Schiagel, C.A. and Flynn,G.L.; US. Patent 3,980,778; September 14,1976; assigned to The Upjohn Co.

General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD01327
ChEBI59750
ChEMBL
Therapeutic Targets DatabaseDAP001184
PharmGKBPA164749408
Drug Product Database481807
RxListhttp://www.rxlist.com/cgi/generic/diflorasone.htm
Drugs.comhttp://www.drugs.com/cdi/diflorasone-diacetate-cream.html
WikipediaDiflorasone
ATC CodesD07AC10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(26.8 KB)
MSDSshow(81.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

References:

  1. Pearce DJ, Spencer L, Hu J, Balkrishnan R, Fleischer AB Jr, Feldman SR: Class I topical corticosteroid use by psoriasis patients in an academic practice. J Dermatolog Treat. 2004 Jul;15(4):235-8. Pubmed

Comments
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Drug created on June 13, 2005 07:24 / Updated on April 14, 2014 11:06