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
CC(=O)OCC(=O)[C@@]12OC(C)(C)O[C@@H]1C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4(F)[C@@H](O)C[C@]23C
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
| Molecular Formula | C26H32F2O7 |
| Molecular Weight | 494.5249 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 9 / 9 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 Date2005 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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 |
|
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013-09-05 |
|
| "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. | 2010-10-10 |
|
| Improvement in treatment adherence with a 3-day course of fluocinonide cream 0.1% for atopic dermatitis. | 2010-10 |
|
| Downstream gene activation of the receptor ALX by the agonist annexin A1. | 2010-09-17 |
|
| Urticarial hypersensitivity reaction caused by temozolomide. | 2010-09 |
|
| Update on the management of chronic eczema: new approaches and emerging treatment options. | 2010-07-28 |
|
| Drug-target interaction prediction from chemical, genomic and pharmacological data in an integrated framework. | 2010-06-15 |
|
| Unusual presentation of cactus spines in the flank of an elderly man: a case report. | 2010-05-25 |
|
| Oral mucous membrane pemphigoid in a 6-year-old boy: diagnosis, treatment and 4 years follow-up. | 2010-01 |
|
| Crusted (Norwegian) scabies following systemic and topical corticosteroid therapy. | 2010-01 |
|
| Drugs for discoid lupus erythematosus. | 2009-10-07 |
|
| Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009-10-02 |
|
| Daily application of fluocinonide 0.1% cream for the treatment of atopic dermatitis. | 2009-09 |
|
| The efficacy of three class I topical synthetic corticosteroids, fluocinonide 0.1% cream, clobetasol 0.05% cream and halobetasol 0.05% cream: a Scholtz-Dumas bioassay comparison. | 2009-08 |
|
| Erythematous papules and pustules on the scalp. | 2009-05-08 |
|
| Effect of intracanal corticosteroids on healing of replanted dog teeth after extended dry times. | 2009-05 |
|
| Case report: Fluocinonide-induced perioral dermatitis in a patient with psoriasis. | 2009-03-15 |
|
| A case of disseminate and recurrent infundibulofolliculitis responsive to treatment with topical steroids. | 2008-11-15 |
|
| Tinea incognito. | 2008-10 |
|
| Bullous mastocytosis: report of a patient and a brief review of the literature. | 2008-10 |
|
| Subcorneal pustular dermatosis (Sneddon-Wilkinson disease) occurring in association with nodal marginal zone lymphoma: a case report. | 2008-08-15 |
|
| Reticulated phototoxic eruption in a patient on long-term diltiazem therapy. | 2008-08 |
|
| CO2 laser evaporation of oral lichen planus. | 2008-07 |
|
| A single-center, double-blind, randomized trial of the atrophogenic effects of fluocinonide cream 0.1% versus clobetasol propionate cream 0.05% in participants with corticosteroid-responsive dermatoses. | 2008-06 |
|
| Calcipotriol/betamethasone dipropionate in the treatment of psoriasis vulgaris. | 2008-02 |
|
| The effect of ceramide-containing skin care products on eczema resolution duration. | 2008-01 |
|
| In vivo determination of the skin atrophy potential of the super-high-potency topical corticosteroid fluocinonide 0.1% cream compared with clobetasol propionate 0.05% cream and foam, and a vehicle. | 2008-01 |
|
| Suppression of the HPA axis in pediatric patients with atopic dermatitis. | 2007-11 |
|
| Left-sided eruption on a child: case study. | 2007-08 |
|
| Guidelines for diagnosis and management of aphthous stomatitis. | 2007-08 |
|
| German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version). | 2007-06 |
|
| Occlusive irritant dermatitis: when is "allergic" contact dermatitis not allergic? | 2007-03-21 |
|
| Successful treatment of inflammatory linear verrucous epidermal nevus with tacrolimus and fluocinonide. | 2007-01-24 |
|
| An open-label adrenal suppression study of 0.1% fluocinonide cream in pediatric patients with atopic dermatitis. | 2006-12 |
|
| Erythematous papular rash on the upper back area. Caterpillar dermatitis, or erucism. | 2006-11 |
|
| Food-induced acute generalized exanthematous pustulosis in a pregnant woman. | 2006-07-21 |
|
| Itchy shoulder with discoloration, pebbly appearance. Patient's only relief comes in form of vigorous back scratching. | 2006-07 |
|
| Oral lichen planus and malignant transformation: a retrospective follow-up study of clinical and histopathologic data. | 2006-04 |
|
| Determination of imperatorin in rat plasma by reversed-phase high-performance liquid chromatography after oral administration of Radix Angelicae dahuricae extract. | 2006-03-18 |
|
| HPLC determination and pharmacokinetics of osthole in rat plasma after oral administration of Fructus Cnidii extract. | 2005-09 |
|
| VANOS (fluocinonide cream, 0.1%). | 2005-07-15 |
|
| Transient band-like keratopathy after treatment for seborrheic dermatitis. | 2005-04 |
|
| Congenital alopecia areata. | 2005-02 |
|
| Fluocinonide. | 2005-01-26 |
|
| Allergic contact dermatitis presenting in the emergency department. | 2005-01 |
|
| Topical tazarotene: a review of its use in the treatment of plaque psoriasis. | 2005 |
|
| Contact allergies to topical corticosteroids. | 1993-03 |
|
| Comparison of amcinonide ointment 0.1 percent twice daily and fluocinonide ointment 0.05 percent three times daily in the treatment of psoriasis. | 1983-05 |
|
| Treatment of psoriasis with amcinonide 0.1 percent and fluocinonide 0.05 percent ointments. A comparative double-blind study. | 1982-06 |
|
| Corticosteroid-induced cutaneous atrophy and telangiectasia. Experimental production associated with weight loss in rats. | 1976-08 |
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
| Substance Class |
Chemical
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2W4A77YPAN
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Validated (UNII)
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N0000175450
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QD07AC08
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QD07CC05
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N0000175576
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NCI_THESAURUS |
C521
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WHO-VATC |
QC05AA11
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Fluocinonide
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Fluocinolide
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D005447
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Fluocinonide
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2W4A77YPAN
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100000090286
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4462
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356-12-7
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m5452
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DB01047
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C29056
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