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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
Prescription ProductsNot Available
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Diflorasone Diacetatecream.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1998-03-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Diflorasone Diacetateointment.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.1999-04-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Diflorasone Diacetatecream.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2002-12-20Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Apexiconointment.5 mg/gtopicalPharmaDerm, A division of Nycomed US Inc.2009-09-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Diflorasone Diacetateointment.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1999-05-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Diflorasone Diacetatecream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2000-04-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Psorconcream5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2014-08-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
FloroneGalderma
Florone ENot Available
MaxiflorNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Diflorasone diacetate
ThumbNot applicableDBSALT000887
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[8.7.0.0²,⁷.0¹¹,¹⁵]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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 17-hydroxysteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Halo-steroid
  • 6-halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Halohydrin
  • Fluorohydrin
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.971
Caco-2 permeable+0.747
P-glycoprotein substrateSubstrate0.7725
P-glycoprotein inhibitor INon-inhibitor0.7629
P-glycoprotein inhibitor IINon-inhibitor0.9002
Renal organic cation transporterNon-inhibitor0.8405
CYP450 2C9 substrateNon-substrate0.8789
CYP450 2D6 substrateNon-substrate0.9031
CYP450 3A4 substrateSubstrate0.6991
CYP450 1A2 substrateNon-inhibitor0.9313
CYP450 2C9 substrateNon-inhibitor0.9254
CYP450 2D6 substrateNon-inhibitor0.939
CYP450 2C19 substrateNon-inhibitor0.9234
CYP450 3A4 substrateNon-inhibitor0.7563
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8979
Ames testNon AMES toxic0.8509
CarcinogenicityNon-carcinogens0.9232
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.3293 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9794
hERG inhibition (predictor II)Non-inhibitor0.6022
Pharmacoeconomics
Manufacturers
  • Altana inc
  • Taro pharmaceuticals usa inc
  • Pharmacia and upjohn co
  • Sanofi aventis us llc
  • Taro pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical.5 mg/g
Creamtopical5 mg/g
Ointmenttopical.5 mg/g
Prices
Unit descriptionCostUnit
Psorcon 0.05% Ointment 60 gm Tube145.75USD tube
Psorcon 0.05% Cream 60 gm Tube137.58USD tube
Diflorasone Diacetate 0.05% Cream 60 gm Tube101.11USD tube
Diflorasone Diacetate 0.05% Ointment 60 gm Tube100.5USD tube
Diflorasone Diacetate 0.05% Cream 30 gm Tube52.81USD tube
Diflorasone Diacetate 0.05% Ointment 30 gm Tube52.29USD tube
Diflorasone Diacetate 0.05% Cream 15 gm Tube38.25USD tube
Diflorasone Diacetate 0.05% Ointment 15 gm Tube38.05USD tube
Psorcon 0.05% cream3.45USD g
Diflorasone 0.05% cream1.5USD g
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 Solubility0.0853 mg/mLALOGPS
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 Area94.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.32 m3·mol-1ChemAxon
Polarizability40.95 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
ATC CodesD07AC10
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (26.8 KB)
MSDSDownload (81.9 KB)
Interactions
Drug Interactions
Drug
AldesleukinCorticosteroids may diminish the antineoplastic effect of Aldesleukin.
DeferasiroxCorticosteroids may enhance the adverse/toxic effect of Deferasirox. Specifically, the risk for GI ulceration/irritation or GI bleeding may be increased.
HyaluronidaseCorticosteroids may diminish the therapeutic effect of Hyaluronidase.
TelaprevirCorticosteroids may decrease the serum concentration of Telaprevir. Telaprevir may increase the serum concentration of Corticosteroids.
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

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