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Fluocinonide (Vanos)

Alias: Lidex, Lyderm, Metosyn, Topsyn,Fluocinolide, Vanos, Lonide
Cat No.:V1707 Purity: ≥98%
Fluocinonide (Lidex,Lyderm, Metosyn, Topsyn,Fluocinolide, Vanos, Lonide) is a potent glucocorticoid/corticosteroid that has been approved for use as a topical anti-inflammatory drug for the treatment of skin disorders such as seborrhoeic dermatitis and eczema.
Fluocinonide (Vanos)
Fluocinonide (Vanos) Chemical Structure CAS No.: 356-12-7
Product category: Calcium Channel
This product is for research use only, not for human use. We do not sell to patients.
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100mg
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500mg
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Fluocinonide (Lidex, Lyderm, Metosyn, Topsyn, Fluocinolide, Vanos, Lonide) is a potent glucocorticoid/corticosteroid that has been approved for use as a topical anti-inflammatory drug for the treatment of skin disorders such as seborrhoeic dermatitis and eczema.

Biological Activity I Assay Protocols (From Reference)
ln Vitro

In vitro activity: Fluocinonide cream has a lower potential to produce atrophic changes of the skin than either clobetasol cream or clobetasol propionate foam. Fluocinonide (Vanos) is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders. Target: Glucocorticoid Receptor Fluocinonide is a potent glucocorticoid steroid used topically as an anti-inflammatory agent for the treatment of skin disorders such as eczema and seborrhoeic dermatitis. Fluocinonide ranks as a high-potency topical corticosteroid. Minimal amounts should be used for a minimal length of time to avoid the occurrence of adverse effects. Fluocinonide should not be used if infection is present. Fluocinonide is used in veterinary medicine. It is a treatment for allergies in dogs. Natural systemic cortisol concentrations can be suppressed for weeks after one week of topical exposure.

ln Vivo
Fluocinonide causes prompt and sustains pituitary-adrenocortical suppression in healthy dogs. Fluocinonide results in significant reduction of plasma cortisol and iACTH concentrations by day 2 of treatment in healthy dog, and the lower concentrations continued to day 5. One week after the last application of Fluocinonide, plasma iACTH concentrations in the corticosteroid-treated dogs has returned to the range of values for the control dogs; however, pre- and post-ACTH cortisol concentrations remains suppressed in Fluocinonide treated dogs. Two weeks after the last treatment, the pre-ACTH plasma cortisol concentrations of corticosteroid-treated dogs returns to those of the control dogs, but the post-ACTH plasma cortisol concentrations remains suppressed.
Animal Protocol

Dogs
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle, the integrity of the epidermal barrier, and the use of occlusive dressings. In general, percutaneous absorption is minimal.
Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Fluocinonide has not been studied during breastfeeding. Since only extensive application of the most potent corticosteroids may cause systemic effects in the mother, it is unlikely that short-term application of topical corticosteroids would pose a risk to the breastfed infant by passage into breastmilk. However, it would be prudent to use the least potent drug on the smallest area of skin possible. It is particularly important to ensure that the infant's skin does not come into direct contact with the areas of skin that have been treated. Only the lower potency corticosteroids should be used on the nipple or areola where the infant could directly ingest the drugs from the skin; fluocinonide should be avoided on the nipple. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking. Any topical corticosteroid should be wiped off thoroughly prior to nursing if it is being applied to the breast or nipple area.
◉ Effects in Breastfed Infants
Topical application of a corticosteroid with relatively high mineralocorticoid activity (isofluprednone acetate) to the mother's nipples resulted in prolonged QT interval, cushingoid appearance, severe hypertension, decreased growth and electrolyte abnormalities in her 2-month-old breastfed infant. The mother had used the cream since birth for painful nipples.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
References
J Drugs Dermatol.2008 Jan;7(1):28-32;J Drugs Dermatol.2008 Jan;7(1):28-32.
Additional Infomation
Fluocinonide is an organic molecular entity.
A topical glucocorticoid used in the treatment of eczema.
Fluocinonide is a Corticosteroid. The mechanism of action of fluocinonide is as a Corticosteroid Hormone Receptor Agonist.
Fluocinonide is a synthetic glucocorticoid and derivative of fluocinolone acetonide with anti-inflammatory and antipruritic activities. Fluocinonide binds the glucocorticoid receptor, followed by translocation of the ligand-receptor complex to the nucleus and transcription activation of genes containing glucocorticoid-responsive elements. Lipocortin-1 is one factor induced by fluocinonide that interacts and inhibits cytosolic phospholipase 2 alpha, thereby preventing phospholipase translocation to the perinuclear membrane and subsequent release and conversion of arachidonic acid to inflammatory prostaglandins. In addition, MAPK phosphatase 1 is induced, thereby preventing the triggering of the MAPK cascade resulting in pro-inflammatory effects via Jun N-terminal kinase and c-Jun. Finally, fluocinonide binds to and inhibits nuclear factor kappa-B directly, resulting in inhibition of cyclooxygenase 2 transcription and subsequent prostaglandin synthesis.
A topical glucocorticoid used in the treatment of ECZEMA.
See also: Fluocinonide; hyaluronate sodium (component of).
Drug Indication
A topical anti-inflammatory product for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
FDA Label
Mechanism of Action
Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. 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.
Pharmacodynamics
Fluocinonide is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders such as eczema. It mediates its effects to relieve itching, redness, dryness, crusting, scaling, inflammation, and discomfort associated with inflammatory skin conditions.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C26H32F2O7
Molecular Weight
494.52
Exact Mass
494.211
CAS #
356-12-7
Related CAS #
356-12-7
PubChem CID
9642
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
591.1±50.0 °C at 760 mmHg
Melting Point
309ºC
Flash Point
311.3±30.1 °C
Vapour Pressure
0.0±3.8 mmHg at 25°C
Index of Refraction
1.560
LogP
3.36
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
4
Heavy Atom Count
35
Complexity
1070
Defined Atom Stereocenter Count
9
SMILES
CC(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@]4([C@H]3C[C@@H](C5=CC(=O)C=C[C@@]54C)F)F)O)C)OC(O2)(C)C
InChi Key
WJOHZNCJWYWUJD-IUGZLZTKSA-N
InChi Code
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
Chemical Name
2-((2S,6aS,6bR,7S,8aS,8bS,11aR,12aS,12bS)-2,6b-difluoro-7-hydroxy-6a,8a,10,10-tetramethyl-4-oxo-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2,1:4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoethyl acetate
Synonyms
Lidex, Lyderm, Metosyn, Topsyn,Fluocinolide, Vanos, Lonide
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO:99 mg/mL (200.2 mM)
Water:<1 mg/mL
Ethanol: N/A
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.0222 mL 10.1108 mL 20.2216 mL
5 mM 0.4044 mL 2.0222 mL 4.0443 mL
10 mM 0.2022 mL 1.0111 mL 2.0222 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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