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Identification
NameFluocinonide
Accession NumberDB01047  (APRD00978)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A topical glucocorticoid used in the treatment of eczema. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
FluocinonideNot AvailableINN, BAN, USAN, JAN
FluocinonidoSpanishINN
FluocinonidumLatinINN
LidexNot AvailableNot Available
VanosNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluocinonidesolution.5 mg/mLtopicalCounty Line Pharmaceuticals, LLC2014-02-28Not AvailableUs
Fluocinonidecream.5 mg/gtopicalLake Erie Medical DBA Quality Care Products LLC1984-06-26Not AvailableUs
Fluocinonidecream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1984-06-26Not AvailableUs
Fluocinonidecream.5 mg/gtopicalA S Medication Solutions Llc1984-06-26Not AvailableUs
Fluocinonidecream.5 mg/gtopicalA S Medication Solutions Llc1984-06-26Not AvailableUs
Fluocinonidecream.5 mg/gtopicalA S Medication Solutions Llc1984-06-26Not AvailableUs
Fluocinonidecream.5 mg/gtopicalPhysicians Total Care, Inc.1984-06-26Not AvailableUs
Vanoscream1 mg/gtopicalPhysicians Total Care, Inc.2010-11-30Not AvailableUs
Fluocinonidecream.5 mg/mLtopicalGolden State Medical Supply, Inc.1984-06-26Not AvailableUs
Fluocinonidecream1 mg/gtopicalOceanside Pharmaceuticals2014-01-06Not AvailableUs
Fluocinonidecream.5 mg/gtopicalPreferred Pharmaceuticals, Inc.2014-05-21Not AvailableUs
Vanoscream1 mg/gtopicalMedicis Pharmaceutical Corp2006-03-13Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Fluocinonidecream.5 mg/gtopicalTeva Pharmaceuticals USA Inc1990-09-30Not AvailableUs
Fluocinonidecream.5 mg/gtopicalTeva Pharmaceuticals USA Inc1990-09-30Not AvailableUs
Fluocinonideointment.5 mg/gtopicalTeva Pharmaceuticals USA Inc1992-05-01Not AvailableUs
Fluocinonidegel.5 mg/gtopicalTeva Pharmaceuticals USA Inc1990-09-30Not AvailableUs
Fluocinonidesolution.5 mg/mLtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.1995-02-27Not AvailableUs
Fluocinonidegel.5 mg/gtopicalE. Fougera & CO., A division of Fougera Pharmaceuticals Inc.1994-12-30Not AvailableUs
Fluocinonidecream.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.1994-10-17Not AvailableUs
Fluocinonideointment.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.1997-08-26Not AvailableUs
Fluocinonidecream.5 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2004-06-23Not AvailableUs
Fluocinonidecream1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2014-07-14Not AvailableUs
Fluocinonidesolution.5 mg/mLtopicalActavis Mid Atlantic LLC2013-07-22Not AvailableUs
Fluocinonidecream.5 mg/gtopicalActavis Mid Atlantic LLC2014-04-09Not AvailableUs
Fluocinonidecream.5 mg/gtopicalSTAT Rx USA LLC1994-10-17Not AvailableUs
Fluocinonidecream.5 mg/gtopicalRebel Distributors Corp1984-06-26Not AvailableUs
Fluocinonideointment.5 mg/gtopicalRebel Distributors Corp2011-01-20Not AvailableUs
Fluocinonidecream1 mg/gtopicalPerrigo New York Inc2014-01-14Not AvailableUs
Fluocinonidecream.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1989-01-19Not AvailableUs
Fluocinonideointment.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1999-06-30Not AvailableUs
Fluocinonidesolution.5 mg/mLtopicalTaro Pharmaceuticals U.S.A., Inc.1996-12-31Not AvailableUs
Fluocinonidegel.5 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1997-07-29Not AvailableUs
Fluocinonidecream1 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.2014-07-14Not AvailableUs
Fluocinonidegel.5 mg/gtopicalH.J. Harkins Company, Inc.2011-01-20Not AvailableUs
Fluocinonideointment.5 mg/gtopicalA S Medication Solutions Llc1999-06-30Not AvailableUs
Fluocinonidecream.5 mg/gtopicalPhysicians Total Care, Inc.1993-12-08Not AvailableUs
Fluocinonidesolution.5 mg/mLtopicalPhysicians Total Care, Inc.1993-05-28Not AvailableUs
Fluocinonidegel.5 mg/gtopicalPhysicians Total Care, Inc.2004-05-20Not AvailableUs
Fluocinonideointment.5 mg/gtopicalPhysicians Total Care, Inc.1994-11-22Not AvailableUs
Fluocinonideointment.5 mg/mLtopicalGolden State Medical Supply, Inc.1997-07-29Not AvailableUs
Fluocinonidesolution.5 mg/mLtopicalGolden State Medical Supply, Inc.1996-12-31Not AvailableUs
Fluocinonidecream.5 mg/gtopicalProficient Rx LP1984-06-26Not AvailableUs
Fluocinonidecream.5 mg/gtopicalMed Vantx, Inc.1990-09-30Not AvailableUs
Fluocinonidecream1 mg/gtopicalGlenmark Generics Inc., USA2014-07-14Not AvailableUs
Fluocinonidecream.5 mg/gtopicalPreferred Pharmaceuticals, Inc.2014-07-30Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
FluonexNot Available
LidexMedicis
Lidex-EMedicis
LonideNot Available
LydermTaro
MetosynBioglan
TopsyminNot Available
TopsynSyntex
Brand mixtures
Brand NameIngredients
Lidecomb CreamFluocinonide + Gramicidin + Neomycin Sulfate + Nystatin
TrisynCiprocinonide + Fluocinonide + Procinonide
SaltsNot Available
Categories
CAS number356-12-7
WeightAverage: 494.5249
Monoisotopic: 494.211609788
Chemical FormulaC26H32F2O7
InChI KeyWJOHZNCJWYWUJD-IUGZLZTKSA-N
InChI
InChI=1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1
IUPAC Name
2-[(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
SMILES
[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@]([H])(F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)COC(C)=O
Taxonomy
DescriptionThis compound 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
  • 20-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Halo-steroid
  • 6-halo-steroid
  • 9-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Alpha-acyloxy ketone
  • Acetate salt
  • Cyclic alcohol
  • Meta-dioxolane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Halohydrin
  • Fluorohydrin
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationA topical anti-inflammatory product for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
PharmacodynamicsFluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. [Wikipedia]
Mechanism of actionFluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort. Fluocinonide binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. Cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In another words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Like other glucocorticoid agents Fluocinolone acetonide acts as a physiological antagonist to insulin by decreasing glycogenesis (formation of glycogen). It also promotes the breakdown of lipids (lipolysis), and proteins, leading to the mobilization of extrahepatic amino acids and ketone bodies. This leads to increased circulating glucose concentrations (in the blood). There is also decreased glycogen formation in the liver.
AbsorptionThe extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle, the integrity of the epidermal barrier, and the use of occlusive dressings. In general, percutaneous absorption is minimal.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationCorticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects may include acne-like eruptions, burning, dryness, excessive hair growth, infection of the skin, irritation, itching, lack of skin color, prickly heat, skin inflammation, skin loss or softening, stretch marks
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+0.9823
Blood Brain Barrier+0.981
Caco-2 permeable-0.5804
P-glycoprotein substrateSubstrate0.7813
P-glycoprotein inhibitor IInhibitor0.8103
P-glycoprotein inhibitor IINon-inhibitor0.5782
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.8667
CYP450 2D6 substrateNon-substrate0.8951
CYP450 3A4 substrateSubstrate0.7219
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9482
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8455
Ames testNon AMES toxic0.7768
CarcinogenicityNon-carcinogens0.9166
BiodegradationNot ready biodegradable1.0
Rat acute toxicity3.1492 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9835
hERG inhibition (predictor II)Non-inhibitor0.6907
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Creamtopical.5 mg/g
Creamtopical.5 mg/mL
Creamtopical1 mg/g
Geltopical.5 mg/g
Ointmenttopical.5 mg/g
Ointmenttopical.5 mg/mL
Solutiontopical.5 mg/mL
Prices
Unit descriptionCostUnit
Vanos 0.1% Cream 60 gm Tube275.75USD tube
Fluocinonide powder176.0USD g
Vanos 0.1% Cream 30 gm Tube155.34USD tube
Fluocinonide 0.05% Ointment 60 gm Tube50.96USD tube
Fluocinonide 0.05% Gel 60 gm Tube50.78USD tube
Fluocinonide-E 0.05% Cream 60 gm Tube47.84USD tube
Fluocinonide 0.05% Gel 30 gm Tube30.1USD tube
Fluocinonide 0.05% Ointment 30 gm Tube28.61USD tube
Fluocinonide-E 0.05% Cream 30 gm Tube28.6USD tube
Fluocinonide 0.05% Solution 60ml Bottle27.23USD bottle
Fluocinonide 0.05% Cream 60 gm Tube22.71USD tube
Fluocinonide 0.05% Solution 20ml Bottle21.99USD bottle
Fluocinonide 0.05% Ointment 15 gm Tube21.88USD tube
Fluocinonide 0.05% Gel 15 gm Tube21.85USD tube
Fluocinonide-E 0.05% Cream 15 gm Tube20.18USD tube
Fluocinonide 0.05% Cream 30 gm Tube13.54USD tube
Fluocinonide 0.05% Cream 15 gm Tube11.99USD tube
Vanos 0.1% cream4.13USD g
Lidex 0.05% cream3.57USD g
Fluocinonide-e 0.05% cream1.33USD g
Fluocinonide 0.05% cream0.6USD g
Fluocinonide-emol 0.05% cream0.4USD g
Lyderm 0.05 % Gel0.38USD g
Lyderm 0.05 % Ointment0.37USD g
Lyderm 0.05 % Cream0.29USD g
Tiamol 0.05 % Emollient Cream0.27USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States67650012001-12-212021-12-21
United States72204242003-01-072023-01-07
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point309 °CPhysProp
water solubility4.74 mg/LNot Available
logP3.19HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0168 mg/mLALOGPS
logP2.93ALOGPS
logP2.05ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)13.55ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity120.56 m3·mol-1ChemAxon
Polarizability49.12 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

US. Patent 3,197,469.

General ReferenceNot Available
External Links
ATC CodesC05AA11D07AC08
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelDownload (818 KB)
MSDSDownload (75.1 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. Jessop S, Whitelaw D, Jordaan F: Drugs for discoid lupus erythematosus. Cochrane Database Syst Rev. 2001;(1):CD002954. Pubmed

2. Smoothened homolog

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Smoothened homolog Q99835 Details

References:

  1. Wang J, Lu J, Bond MC, Chen M, Ren XR, Lyerly HK, Barak LS, Chen W: Identification of select glucocorticoids as Smoothened agonists: potential utility for regenerative medicine. Proc Natl Acad Sci U S A. 2010 May 18;107(20):9323-8. Epub 2010 May 3. Pubmed

Carriers

1. Corticosteroid-binding globulin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Corticosteroid-binding globulin P08185 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments
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Drug created on June 13, 2005 07:24 / Updated on April 23, 2014 15:47