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
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 |
---|---|---|---|---|
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 |
---|---|---|
Corticosteroid-induced cutaneous atrophy and telangiectasia. Experimental production associated with weight loss in rats. | 1976 Aug |
|
Calcipotriol ointment. A review of its use in the management of psoriasis. | 2001 |
|
[Oral lichen planus. 2. Therapy possibilities and current treatment concepts]. | 2001 |
|
Oral lichen planus: patient profile, disease progression and treatment responses. | 2001 Jul |
|
Pyostomatitis vegetans as an early sign of reactivation of Crohn's disease: a case report. | 2002 Dec |
|
Iguana bite-induced hypersensitivity reaction. | 2003 Dec |
|
Peristomal lichen sclerosus developing posturostomy. | 2003 Mar |
|
Lack of effect of long-term octreotide therapy in severe thyroid-associated dermopathy. | 2003 May |
|
Desquamative gingivitis: early presenting symptom of mucocutaneous disease. | 2003 Sep |
|
Allergic contact dermatitis presenting in the emergency department. | 2005 Jan |
|
Fluocinonide. | 2005 Jan 4-10 |
|
Itchy shoulder with discoloration, pebbly appearance. Patient's only relief comes in form of vigorous back scratching. | 2006 Jul |
|
Food-induced acute generalized exanthematous pustulosis in a pregnant woman. | 2006 Jul-Aug |
|
Left-sided eruption on a child: case study. | 2007 Aug |
|
Suppression of the HPA axis in pediatric patients with atopic dermatitis. | 2007 Nov |
|
Reticulated phototoxic eruption in a patient on long-term diltiazem therapy. | 2008 Aug |
|
Subcorneal pustular dermatosis (Sneddon-Wilkinson disease) occurring in association with nodal marginal zone lymphoma: a case report. | 2008 Aug 15 |
|
Calcipotriol/betamethasone dipropionate in the treatment of psoriasis vulgaris. | 2008 Feb |
|
The effect of ceramide-containing skin care products on eczema resolution duration. | 2008 Jan |
|
CO2 laser evaporation of oral lichen planus. | 2008 Jul |
|
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 Jun |
|
A case of disseminate and recurrent infundibulofolliculitis responsive to treatment with topical steroids. | 2008 Nov 15 |
|
Tinea incognito. | 2008 Oct |
|
Bullous mastocytosis: report of a patient and a brief review of the literature. | 2008 Oct |
|
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 Aug |
|
Case report: Fluocinonide-induced perioral dermatitis in a patient with psoriasis. | 2009 Mar 15 |
|
Erythematous papules and pustules on the scalp. | 2009 Mar-Apr |
|
Effect of intracanal corticosteroids on healing of replanted dog teeth after extended dry times. | 2009 May |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
Drugs for discoid lupus erythematosus. | 2009 Oct 7 |
|
Daily application of fluocinonide 0.1% cream for the treatment of atopic dermatitis. | 2009 Sep |
|
Oral mucous membrane pemphigoid in a 6-year-old boy: diagnosis, treatment and 4 years follow-up. | 2010 Jan |
|
Crusted (Norwegian) scabies following systemic and topical corticosteroid therapy. | 2010 Jan |
|
Drug-target interaction prediction from chemical, genomic and pharmacological data in an integrated framework. | 2010 Jun 15 |
|
Unusual presentation of cactus spines in the flank of an elderly man: a case report. | 2010 May 25 |
|
Improvement in treatment adherence with a 3-day course of fluocinonide cream 0.1% for atopic dermatitis. | 2010 Oct |
|
"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 |
|
Downstream gene activation of the receptor ALX by the agonist annexin A1. | 2010 Sep 17 |
|
FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
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
Created
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on
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Record UNII |
2W4A77YPAN
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Validated (UNII)
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WHO-ATC |
C05AA11
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NDF-RT |
N0000175450
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QD07AC08
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QD07CC05
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WHO-ATC |
D07AC08
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D07CC05
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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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4462
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356-12-7
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m5452
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1205
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2578
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DTXSID8045307
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DB01047
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C29056
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101791
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CHEMBL1501
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2W4A77YPAN
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