Identification
- Summary
Diflorasone is a topical corticosteroid used to treat the symptoms of various inflammatory skin conditions that cause erythema, pruritus, and discomfort.
- Brand Names
- Apexicon, Florone, Psorcon
- Generic Name
- Diflorasone
- DrugBank Accession Number
- DB00223
- Background
Diflorasone is a topical corticosteroid used to treat itching and inflammation of the skin.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Diflorasone (DB00223)
- Weight
- Average: 410.4515
Monoisotopic: 410.190480416 - Chemical Formula
- C22H28F2O5
- Synonyms
- (6α,11β,16β)-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione
- Diflorasona
- Diflorasone
- Diflorasonum
Pharmacology
- Indication
For relief of the inflammatory and pruritic manifestations of corticosteroid responsive dermatoses.
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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AGlucocorticoid receptor agonistHumans - 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
- Adverse Effects
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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).
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose The risk or severity of hyperglycemia can be increased when Diflorasone is combined with Acarbose. Acetohexamide The risk or severity of hyperglycemia can be increased when Diflorasone is combined with Acetohexamide. Acetyldigitoxin The risk or severity of adverse effects can be increased when Diflorasone is combined with Acetyldigitoxin. Albiglutide The risk or severity of hyperglycemia can be increased when Diflorasone is combined with Albiglutide. Allogeneic processed thymus tissue The therapeutic efficacy of Allogeneic processed thymus tissue can be decreased when used in combination with Diflorasone. Alogliptin The risk or severity of hyperglycemia can be increased when Diflorasone is combined with Alogliptin. Aminoglutethimide The therapeutic efficacy of Diflorasone can be decreased when used in combination with Aminoglutethimide. Bendroflumethiazide The risk or severity of electrolyte imbalance can be increased when Diflorasone is combined with Bendroflumethiazide. Benzthiazide The risk or severity of electrolyte imbalance can be increased when Diflorasone is combined with Benzthiazide. Bromocriptine The risk or severity of hyperglycemia can be increased when Diflorasone is combined with Bromocriptine. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Diflorasone diacetate 7W2J09SCWX 33564-31-7 BOBLHFUVNSFZPJ-JOYXJVLSSA-N - International/Other Brands
- Florone E / Maxiflor
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Florone Cream 0.5 mg/1g Topical Pharmacia and Upjohn Division of Pfizer 2006-02-06 Not applicable US 
Florone Crm 0.05% Cream .05 % Topical Upjohn 1980-12-31 1998-08-12 Canada 
Florone Ont 0.05% Ointment .05 % Topical Upjohn 1980-12-31 1998-08-12 Canada Psorcon Cream 0.5 mg/60g Topical Dermik Laboratories, Inc. 2009-01-16 Not applicable US Psorcon Ointment 0.5 mg/1g Topical Physicians Total Care, Inc. 1985-08-28 2002-06-30 US Psorcon Ointment 0.5 mg/1g Topical Dermik Laboratories, Inc. 2006-02-06 Not applicable US Psorcon E Cream 0.5 mg/1g Topical Dermik Laboratories, Inc. 2007-08-04 Not applicable US Psorcon E Ointment 0.5 mg/1g Topical Dermik Laboratories, Inc. 2006-02-06 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image ApexiCon Ointment 0.5 mg/1g Topical Fougera Pharmaceuticals Inc. 2009-09-30 2014-05-31 US ApexiCon E Cream 0.5 mg/1g Topical Pharma Derm, A Division Of Fougera Pharmaceuticals Inc. 2009-09-30 2014-06-30 US ApexiCon E Cream 0.5 mg/1g Topical PharmaDerm a division of Fougera Pharmaceuticals Inc. 2002-12-20 2023-04-28 US ApexiCon E Cream 0.5 mg/1g Topical ANI Pharmaceuticals, Inc. 2022-10-20 Not applicable US Diflorasone Diacetate Ointment 0.5 mg/1g Topical E. Fougera & CO., A division of Fougera Pharmaceuticals Inc. 1999-04-27 Not applicable US Diflorasone Diacetate Cream 0.5 mg/1g Topical Emerald Therapeutics, LLC 2000-04-24 Not applicable US Diflorasone Diacetate Ointment 0.5 mg/1g Topical Innovida Pharmaceutique Corporation 2018-08-15 Not applicable US Diflorasone Diacetate Ointment 0.5 mg/1g Topical Rising Pharmaceuticals, Inc. 2017-02-27 Not applicable US Diflorasone Diacetate Cream 0.5 mg/1g Topical E. Fougera & CO., A division of Fougera Pharmaceuticals Inc. 1998-03-30 Not applicable US Diflorasone Diacetate Ointment 0.5 mg/1g Topical Taro Pharmaceuticals U.S.A., Inc. 1999-05-14 Not applicable US
Categories
- ATC Codes
- D07AC10 — Diflorasone
- Drug Categories
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Corticosteroid Hormone Receptor Agonists
- Corticosteroids
- Corticosteroids, Dermatological Preparations
- Corticosteroids, Potent (Group III)
- Dermatologicals
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Immunosuppressive Agents
- Pregnadienes
- Pregnadienetriols
- Pregnanes
- Steroids
- Steroids, Fluorinated
- Chemical TaxonomyProvided by Classyfire
- 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
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / 6-halo-steroid / 9-halo-steroid / Alcohol 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)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- T2DHJ9645W
- CAS number
- 2557-49-5
- 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,3aS,3bS,5S,9aS,9bR,10S,11aS)-5,9b-difluoro-1,10-dihydroxy-1-(2-hydroxyacetyl)-2,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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
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
- FDA Approved Drug Products: PSORCON (diflorasone diacetate) ointment [Link]
- External Links
- Human Metabolome Database
- HMDB0014368
- KEGG Drug
- D07827
- PubChem Compound
- 71415
- PubChem Substance
- 46504519
- ChemSpider
- 64505
- 91311
- ChEBI
- 59750
- ChEMBL
- CHEMBL1201380
- ZINC
- ZINC000005752191
- Therapeutic Targets Database
- DAP001184
- PharmGKB
- PA164749408
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Diflorasone
- FDA label
- Download (26.8 KB)
- MSDS
- Download (81.9 KB)
Clinical Trials
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
Form Route Strength Cream Topical 0.5 mg/1g Cream Topical .05 % Ointment Topical .05 % Cream Topical 0.5 mg/60g Cream Topical 5 mg/1g Ointment Topical 0.5 mg/1g Cream Topical Ointment Topical - Prices
Unit description Cost Unit Psorcon 0.05% Ointment 60 gm Tube 145.75USD tube Psorcon 0.05% Cream 60 gm Tube 137.58USD tube Diflorasone Diacetate 0.05% Cream 60 gm Tube 101.11USD tube Diflorasone Diacetate 0.05% Ointment 60 gm Tube 100.5USD tube Diflorasone Diacetate 0.05% Cream 30 gm Tube 52.81USD tube Diflorasone Diacetate 0.05% Ointment 30 gm Tube 52.29USD tube Diflorasone Diacetate 0.05% Cream 15 gm Tube 38.25USD tube Diflorasone Diacetate 0.05% Ointment 15 gm Tube 38.05USD tube Psorcon 0.05% cream 3.45USD g Diflorasone 0.05% cream 1.5USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0853 mg/mL ALOGPS logP 1.91 ALOGPS logP 1.34 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 12.42 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 94.83 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 102.32 m3·mol-1 Chemaxon Polarizability 40.92 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.9254 CYP450 2D6 inhibitor Non-inhibitor 0.939 CYP450 2C19 inhibitor Non-inhibitor 0.9234 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:18