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

1.10799356E12
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
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
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 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
NDF-RT N0000175450
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
WHO-VATC QD07AC08
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
WHO-VATC QD07CC05
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
WHO-ATC D07AC08
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
WHO-ATC D07CC05
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
NDF-RT N0000175576
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
NCI_THESAURUS C521
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
WHO-VATC QC05AA11
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
Code System Code Type Description
EVMPD
SUB07715MIG
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
PUBCHEM
9642
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
IUPHAR
7078
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
LACTMED
Fluocinonide
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
LACTMED
Fluocinolide
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
MESH
D005447
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
WIKIPEDIA
Fluocinonide
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-597-6
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
RS_ITEM_NUM
1276001
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
FDA UNII
2W4A77YPAN
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
SMS_ID
100000090286
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
RXCUI
4462
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY RxNorm
CAS
356-12-7
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
MERCK INDEX
m5452
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY Merck Index
DRUG CENTRAL
1205
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
INN
2578
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
EPA CompTox
DTXSID8045307
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
DRUG BANK
DB01047
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
NCI_THESAURUS
C29056
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
NSC
101791
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
ChEMBL
CHEMBL1501
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY
DAILYMED
2W4A77YPAN
Created by admin on Fri Dec 15 15:09:12 UTC 2023 , Edited by admin on Fri Dec 15 15:09:12 UTC 2023
PRIMARY