Identification

Name
Diflorasone
Accession Number
DB00223  (APRD00921)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • (6alpha,11beta,16beta)-6,9-Difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
  • (6α,11β,16β)-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
  • Diflorasona
  • Diflorasonum
Product Ingredients
IngredientUNIICASInChI Key
Diflorasone diacetate7W2J09SCWX33564-31-7BOBLHFUVNSFZPJ-JOYXJVLSSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Florone Crm 0.05%Cream.05 %TopicalUpjohn1980-12-311998-08-12Canada
Florone Ont 0.05%Ointment.05 %TopicalUpjohn1980-12-311998-08-12Canada
PsorconOintment0.5 mg/1gTopicalPhysicians Total Care, Inc.1985-08-282002-06-30Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
ApexiConOintment0.5 mg/1gTopicalPharma Derm, A Division Of Nycomed Us Inc.2009-09-30Not applicableUs
ApexiCon ECream0.5 mg/1gTopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2002-12-20Not applicableUs
ApexiCon ECream0.5 mg/1gTopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.2009-09-302014-06-30Us
Diflorasone DiacetateCream0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.2000-04-24Not applicableUs
Diflorasone DiacetateOintment0.5 mg/1gTopicalInnovida Pharmaceutique Corporation2018-08-15Not applicableUs
Diflorasone DiacetateOintment0.5 mg/1gTopicalTeligent Pharma, Inc.2018-06-13Not applicableUs
Diflorasone DiacetateOintment0.5 mg/1gTopicalVersa Pharm Incorporated2016-03-08Not applicableUs
Diflorasone DiacetateOintment0.5 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.1999-05-14Not applicableUs
Diflorasone DiacetateOintment0.5 mg/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1999-04-27Not applicableUs
Diflorasone DiacetateCream0.5 mg/1gTopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1998-03-30Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
FloroneDiflorasone diacetate (0.5 mg/1g)CreamTopicalPharmacia and Upjohn Division of Pfizer2006-02-06Not applicableUs
PsorconDiflorasone diacetate (0.5 mg/1g)OintmentTopicalDermik Laboratories, Inc.2006-02-06Not applicableUs
PsorconDiflorasone diacetate (0.5 mg/60g)CreamTopicalDermik Laboratories, Inc.2009-01-16Not applicableUs
Psorcon EDiflorasone diacetate (0.5 mg/1g)CreamTopicalDermik Laboratories, Inc.2007-08-04Not applicableUs
Psorcon EDiflorasone diacetate (0.5 mg/1g)OintmentTopicalDermik Laboratories, Inc.2006-02-06Not applicableUs
International/Other Brands
Florone (Galderma) / Florone E / Maxiflor
Categories
UNII
T2DHJ9645W
CAS number
2557-49-5
Weight
Average: 410.4515
Monoisotopic: 410.190480416
Chemical Formula
C22H28F2O5
InChI Key
WXURHACBFYSXBI-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

Pharmacology

Indication

For relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.

Associated Conditions
Pharmacodynamics

Like 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 action

The 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.

TargetActionsOrganism
AGlucocorticoid receptor
agonist
Human
Absorption

Topical 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 distribution
Not Available
Protein binding

Bound to plasma proteins in varying degrees.

Metabolism

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

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Topically 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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Diflorasone.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Diflorasone.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Diflorasone.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Diflorasone.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Diflorasone.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Diflorasone.
4-HydroxytestosteroneThe risk or severity of edema formation can be increased when 4-Hydroxytestosterone is combined with Diflorasone.
5-androstenedioneThe risk or severity of edema formation can be increased when 5-androstenedione is combined with Diflorasone.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when 9-(N-methyl-L-isoleucine)-cyclosporin A is combined with Diflorasone.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Diflorasone.
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0014368
KEGG Drug
D01327
PubChem Compound
71415
PubChem Substance
46504519
ChemSpider
64505
ChEBI
59750
ChEMBL
CHEMBL1201380
Therapeutic Targets Database
DAP001184
PharmGKB
PA164749408
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Diflorasone
ATC Codes
D07AC10 — Diflorasone
FDA label
Download (26.8 KB)
MSDS
Download (81.9 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Altana inc
  • Taro pharmaceuticals usa inc
  • Pharmacia and upjohn co
  • Sanofi aventis us llc
  • Taro pharmaceuticals inc
Packagers
  • Allergan Inc.
  • Dermik Labs
  • Dispensing Solutions
  • E. Fougera and Co.
  • Lake Erie Medical and Surgical Supply
  • Nycomed Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Taro Pharmaceuticals USA
Dosage forms
FormRouteStrength
CreamTopical0.5 mg/1g
CreamTopical.05 %
OintmentTopical.05 %
CreamTopical0.5 mg/60g
CreamTopical5 mg/1g
OintmentTopical0.5 mg/1g
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.
Patents
Not Available

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.9254
CYP450 2D6 inhibitorNon-inhibitor0.939
CYP450 2C19 inhibitorNon-inhibitor0.9234
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

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 molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-1,4-steroids / Halogenated steroids / Delta-1,4-steroids / Tertiary alcohols / Alpha-hydroxy ketones / Secondary alcohols
show 8 more
Substituents
Progestogin-skeleton / 21-hydroxysteroid / Pregnane-skeleton / 20-oxosteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 17-hydroxysteroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / 9-halo-steroid
show 24 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid, 20-oxo steroid, fluorinated steroid, 3-oxo-Delta(1),Delta(4)-steroid, 21-hydroxy steroid (CHEBI:59750)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
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:15764038]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2018 07:45