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 |
---|---|---|
Treatment of psoriasis with amcinonide 0.1 percent and fluocinonide 0.05 percent ointments. A comparative double-blind study. | 1982 Jun |
|
Comparison of amcinonide ointment 0.1 percent twice daily and fluocinonide ointment 0.05 percent three times daily in the treatment of psoriasis. | 1983 May |
|
Contact allergies to topical corticosteroids. | 1993 Mar |
|
[Oral lichen planus. 2. Therapy possibilities and current treatment concepts]. | 2001 |
|
What's your assessment? Psoriasis with steroid atrophy. | 2001 Aug |
|
Targeting keratinocyte apoptosis in the treatment of atopic dermatitis and allergic contact dermatitis. | 2001 Nov |
|
Cutaneous sarcoidosis of the scrotum: a rare manifestation of systemic disease. | 2002 |
|
Iguana bite-induced hypersensitivity reaction. | 2003 Dec |
|
Lack of effect of long-term octreotide therapy in severe thyroid-associated dermopathy. | 2003 May |
|
Fluocinonide. | 2005 Jan 4-10 |
|
HPLC determination and pharmacokinetics of osthole in rat plasma after oral administration of Fructus Cnidii extract. | 2005 Sep |
|
Erythematous papular rash on the upper back area. Caterpillar dermatitis, or erucism. | 2006 Nov |
|
Left-sided eruption on a child: case study. | 2007 Aug |
|
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 |
|
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 |
|
Drugs associated with more suicidal ideations are also associated with more suicide attempts. | 2009 Oct 2 |
|
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
by
admin
on
Edited
Mon Mar 31 17:48:15 GMT 2025
by
admin
on
Mon Mar 31 17:48:15 GMT 2025
|
Record UNII |
2W4A77YPAN
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Preferred Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
C05AA11
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
NDF-RT |
N0000175450
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
WHO-VATC |
QD07AC08
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
WHO-VATC |
QD07CC05
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
WHO-ATC |
D07AC08
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
WHO-ATC |
D07CC05
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
NDF-RT |
N0000175576
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
NCI_THESAURUS |
C521
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
||
|
WHO-VATC |
QC05AA11
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB07715MIG
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
9642
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
7078
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
Fluocinonide
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
Fluocinolide
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
D005447
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
Fluocinonide
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
206-597-6
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
1276001
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
2W4A77YPAN
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
100000090286
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
4462
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | RxNorm | ||
|
356-12-7
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
m5452
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | Merck Index | ||
|
1205
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
2578
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
DTXSID8045307
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
DB01047
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
C29056
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
101791
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
CHEMBL1501
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY | |||
|
2W4A77YPAN
Created by
admin on Mon Mar 31 17:48:15 GMT 2025 , Edited by admin on Mon Mar 31 17:48:15 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> IMPURITY |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|