U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of FLUOCINONIDE

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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Vanos

Approved Use

indicated for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.

Launch Date

2005
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
54 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
354.8 ng × h/mL
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
14.8 h
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
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Drugs for discoid lupus erythematosus.
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
Lack of effect of long-term octreotide therapy in severe thyroid-associated dermopathy.
2003 May
Determination of imperatorin in rat plasma by reversed-phase high-performance liquid chromatography after oral administration of Radix Angelicae dahuricae extract.
2006 Mar 18
Erythematous papular rash on the upper back area. Caterpillar dermatitis, or erucism.
2006 Nov
Occlusive irritant dermatitis: when is "allergic" contact dermatitis not allergic?
2007 Mar-Apr
The effect of ceramide-containing skin care products on eczema resolution duration.
2008 Jan
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 for discoid lupus erythematosus.
2009 Oct 7
Oral mucous membrane pemphigoid in a 6-year-old boy: diagnosis, treatment and 4 years follow-up.
2010 Jan
Unusual presentation of cactus spines in the flank of an elderly man: a case report.
2010 May 25
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
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
Name Type Language
FLUOCINONIDE
INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
FLUOCINONIDE [USAN]
Common Name English
fluocinonide [INN]
Common Name English
VANOS
Brand Name English
FLUOCINOLONE ACETONIDE IMPURITY M [EP IMPURITY]
Common Name English
FLUOCINONIDE [JAN]
Common Name English
Fluocinonide [WHO-DD]
Common Name English
FLUOCINONIDE [MI]
Common Name English
FLUOCINONIDE [MART.]
Common Name English
FLUOCINONIDE [ORANGE BOOK]
Common Name English
LIDEX
Brand Name English
PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-6,9-DIFLUORO-11-HYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-, (6.ALPHA.,11.BETA.,16.ALPHA.)-
Common Name English
6α,9-Difluoro-11β,16α,17,21-tetrahydroxypregna-1,4-diene-3,20-dione, cyclic 16,17-acetal with acetone, 21-acetate
Common Name English
FLUOCINONIDE [USP-RS]
Common Name English
FLUOCINOLIDE
Common Name English
FLUOCINONIDE [USP IMPURITY]
Common Name English
NSC-101791
Code English
FLUOCINONIDE [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC C05AA11
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
NDF-RT N0000175450
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WHO-VATC QD07AC08
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WHO-VATC QD07CC05
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WHO-ATC D07AC08
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
WHO-ATC D07CC05
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
NCI_THESAURUS C521
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WHO-VATC QC05AA11
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Code System Code Type Description
EVMPD
SUB07715MIG
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PRIMARY
PUBCHEM
9642
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PRIMARY
IUPHAR
7078
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PRIMARY
LACTMED
Fluocinonide
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PRIMARY
LACTMED
Fluocinolide
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PRIMARY
MESH
D005447
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PRIMARY
WIKIPEDIA
Fluocinonide
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PRIMARY
ECHA (EC/EINECS)
206-597-6
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PRIMARY
RS_ITEM_NUM
1276001
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PRIMARY
FDA UNII
2W4A77YPAN
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PRIMARY
SMS_ID
100000090286
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PRIMARY
RXCUI
4462
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PRIMARY RxNorm
CAS
356-12-7
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PRIMARY
MERCK INDEX
m5452
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PRIMARY Merck Index
DRUG CENTRAL
1205
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PRIMARY
INN
2578
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PRIMARY
EPA CompTox
DTXSID8045307
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PRIMARY
DRUG BANK
DB01047
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PRIMARY
NCI_THESAURUS
C29056
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
PRIMARY
NSC
101791
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL1501
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
PRIMARY
DAILYMED
2W4A77YPAN
Created by admin on Fri Dec 15 15:09:12 GMT 2023 , Edited by admin on Fri Dec 15 15:09:12 GMT 2023
PRIMARY