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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
SaltsNot Available
Brand names
NameCompany
FluonexNot Available
LidexNot Available
Lidex-ENot Available
LonideNot Available
LydermNot Available
MetosynNot Available
TopsyminNot Available
TopsynNot Available
VanosNot Available
Brand mixtures
Brand NameIngredients
Lidecomb CreamFluocinonide + Gramicidin + Neomycin Sulfate + Nystatin
TrisynCiprocinonide + Fluocinonide + Procinonide
Categories
CAS number356-12-7
WeightAverage: 494.5249
Monoisotopic: 494.211609788
Chemical FormulaC26H32F2O7
InChI KeyInChIKey=WJOHZNCJWYWUJD-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[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHydroxysteroids; Halogenated Steroids; Ketosteroids; Cyclohexanols; 1,3-Dioxolanes; Fluorohydrins; Carboxylic Acid Esters; Cyclic Alcohols and Derivatives; Ketones; Enolates; Polyamines; Acetals; Aldehydes; Alkyl Fluorides; Organofluorides
Substituents20-keto-steroid; 3-keto-steroid; 11-hydroxy-steroid; 6-halo-steroid; 9-halo-steroid; cyclohexanol; meta-dioxolane; cyclic alcohol; secondary alcohol; carboxylic acid ester; ketone; halohydrin; fluorohydrin; enolate; acetal; ether; polyamine; carboxylic acid derivative; organofluoride; carbonyl group; alkyl halide; alkyl fluoride; organohalogen; alcohol; 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
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
Property Value Probability
Human Intestinal Absorption + 0.9823
Blood Brain Barrier + 0.981
Caco-2 permeable - 0.5804
P-glycoprotein substrate Substrate 0.7813
P-glycoprotein inhibitor I Inhibitor 0.8103
P-glycoprotein inhibitor II Non-inhibitor 0.5782
Renal organic cation transporter Non-inhibitor 0.8178
CYP450 2C9 substrate Non-substrate 0.8667
CYP450 2D6 substrate Non-substrate 0.8951
CYP450 3A4 substrate Substrate 0.7219
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9482
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8455
Ames test Non AMES toxic 0.7768
Carcinogenicity Non-carcinogens 0.9166
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 3.1492 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9835
hERG inhibition (predictor II) Non-inhibitor 0.6907
Pharmacoeconomics
Manufacturers
  • Actavis mid atlantic llc
  • E fougera div altana inc
  • Perrigo new york inc
  • Taro pharmaceuticals usa inc
  • Teva pharmaceuticals usa inc
  • Altana inc
  • Medicis pharmaceutical corp
  • Taro pharmaceuticals inc
  • Teva pharmaceuticals usa
Packagers
Dosage forms
FormRouteStrength
CreamTopical
GelTopical
OintmentTopical
Prices
Unit descriptionCostUnit
Vanos 0.1% Cream 60 gm Tube275.75USDtube
Fluocinonide powder176.0USDg
Vanos 0.1% Cream 30 gm Tube155.34USDtube
Fluocinonide 0.05% Ointment 60 gm Tube50.96USDtube
Fluocinonide 0.05% Gel 60 gm Tube50.78USDtube
Fluocinonide-E 0.05% Cream 60 gm Tube47.84USDtube
Fluocinonide 0.05% Gel 30 gm Tube30.1USDtube
Fluocinonide 0.05% Ointment 30 gm Tube28.61USDtube
Fluocinonide-E 0.05% Cream 30 gm Tube28.6USDtube
Fluocinonide 0.05% Solution 60ml Bottle27.23USDbottle
Fluocinonide 0.05% Cream 60 gm Tube22.71USDtube
Fluocinonide 0.05% Solution 20ml Bottle21.99USDbottle
Fluocinonide 0.05% Ointment 15 gm Tube21.88USDtube
Fluocinonide 0.05% Gel 15 gm Tube21.85USDtube
Fluocinonide-E 0.05% Cream 15 gm Tube20.18USDtube
Fluocinonide 0.05% Cream 30 gm Tube13.54USDtube
Fluocinonide 0.05% Cream 15 gm Tube11.99USDtube
Vanos 0.1% cream4.13USDg
Lidex 0.05% cream3.57USDg
Fluocinonide-e 0.05% cream1.33USDg
Fluocinonide 0.05% cream0.6USDg
Fluocinonide-emol 0.05% cream0.4USDg
Lyderm 0.05 % Gel0.38USDg
Lyderm 0.05 % Ointment0.37USDg
Lyderm 0.05 % Cream0.29USDg
Tiamol 0.05 % Emollient Cream0.27USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States72204242003-01-072023-01-07
United States67650012001-12-212021-12-21
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point309 °CPhysProp
water solubility4.74 mg/LNot Available
logP3.19HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.68e-02 g/lALOGPS
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 area99.13ChemAxon
rotatable bond count4ChemAxon
refractivity120.56ChemAxon
polarizability49.12ChemAxon
number of rings5ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00325
PubChem Compound9642
PubChem Substance46504523
ChemSpider9265
Therapeutic Targets DatabaseDAP000421
PharmGKBPA449664
Drug Product Database716863
RxListhttp://www.rxlist.com/cgi/generic2/fluocin.htm
Drugs.comhttp://www.drugs.com/cdi/fluocinonide-cream.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/lid1227.shtml
WikipediaFluocinonide
ATC CodesC05AA11D07AC08
AHFS Codes
  • 84:06.00
PDB EntriesNot Available
FDA labelshow(818 KB)
MSDSshow(75.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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

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
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13