Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H32F2O7 |
Molecular Weight | 494.5249 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
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
InChI
InChIKey=WJOHZNCJWYWUJD-IUGZLZTKSA-N
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
DescriptionSources: http://www.drugbank.ca/drugs/DB01047Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/fluocinonide.html
Sources: http://www.drugbank.ca/drugs/DB01047
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/fluocinonide.html
Fluocinonide 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. Fluocinonide is used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Fluocinonide is marketed under the names Fluonex, Lidex, Lidex-E, Lonide, Lyderm, and Vanos.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB01047 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Vanos Approved Useindicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Launch Date1.10799356E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
54 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1874579/ |
0.8 mg single, topical dose: 0.8 mg route of administration: Topical experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
43.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1874579/ |
0.8 mg single, transdermal dose: 0.8 mg route of administration: Transdermal experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
354.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1874579/ |
0.8 mg single, topical dose: 0.8 mg route of administration: Topical experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
363.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1874579/ |
0.8 mg single, transdermal dose: 0.8 mg route of administration: Transdermal experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1874579/ |
0.8 mg single, topical dose: 0.8 mg route of administration: Topical experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1874579/ |
0.8 mg single, transdermal dose: 0.8 mg route of administration: Transdermal experiment type: SINGLE co-administered: |
FLUOCINOLONE ACETONIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
---|---|---|
Contact allergies to topical corticosteroids. | 1993 Mar |
|
The effect of two skin cleansing systems on moderate xerotic eczema. | 2004 Jun |
|
Transient band-like keratopathy after treatment for seborrheic dermatitis. | 2005 Apr |
|
VANOS (fluocinonide cream, 0.1%). | 2005 Jul-Aug |
|
Food-induced acute generalized exanthematous pustulosis in a pregnant woman. | 2006 Jul-Aug |
|
Determination of imperatorin in rat plasma by reversed-phase high-performance liquid chromatography after oral administration of Radix Angelicae dahuricae extract. | 2006 Mar 18 |
|
German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version). | 2007 Jun |
|
The effect of ceramide-containing skin care products on eczema resolution duration. | 2008 Jan |
|
A case of disseminate and recurrent infundibulofolliculitis responsive to treatment with topical steroids. | 2008 Nov 15 |
|
Erythematous papules and pustules on the scalp. | 2009 Mar-Apr |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Crusted (Norwegian) scabies following systemic and topical corticosteroid therapy. | 2010 Jan |
|
"For export only" medicines come back to Europe: a RP-LC method for the screening of six glucocorticoids in illegal and counterfeit anti-inflammatory and lightening creams. | 2010 Oct 10 |
|
Urticarial hypersensitivity reaction caused by temozolomide. | 2010 Sep |
Patents
Sample Use Guides
0.05% cream, gel, ointment: Apply a thin layer to affected area two to four times a day 0.1% cream: Apply a thin layer to affected area once or twice a day
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/856468
Fluocinonide was found to be potent inhibitor of tumor promotion in
mouse skin when administered topically at 10 ug/0.2ml simultaneous with each exposure to TPA
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QC05AA11
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Fluocinonide
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ACTIVE MOIETY