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Home > Encyclopedia > Fluocinonide

Fluocinonide

pharmaceutical raw materials
Fluocinonide structure

Fluocinonide 

structure
  • CAS No:

    356-12-7

  • Formula:

    C26H32F2O7

  • Chemical Name:

    Fluocinonide

  • Synonyms:

    Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-,(6α,11β,16α)-;Pregna-1,4-diene-3,20-dione,6α,9-difluoro-11β,16α,17,21-tetrahydroxy-,cyclic 16,17-acetal with acetone,21-acetate;2H-Naphth[2′,1′:4,5]indeno[1,2-d][1,3]dioxole,pregna-1,4-diene-3,20-dione deriv.;(6α,11β,16α)-21-(Acetyloxy)-6,9-difluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione;Fluocinolone acetonide acetate;Fluocinolide;Fluocinonide;Fluocinolone acetonide 21-acetate;Metosyn;Lidex E;Fluocinolide acetate;Flucinar;Topsym;Lidex;Topsymin;NSC 101791;Topsyne;Straderm;Dermaplus;Topsyn;Biscosal;Flucetonide;Vanos

  • Categories:

    Active Pharmaceutical Ingredients  >  Hormones and the Endocrine System

Description

Fluocinonide (Vanos) is a potent glucocorticoid steroid used topically as anti-inflammatory agent for the treatment of skin disorders.Target: Glucocorticoid ReceptorFluocinonide 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 adver


Solid


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.

Fluocinonide Basic Attributes

494.52

494.52

206-597-6

2W4A77YPAN

DTXSID8045307

C29056

C - Cardiovascular system|D - Dermatologicals

2937210000

Characteristics

99.13000

3.36

white to tan

1.3±0.1 g/cm3

309 °C

591.1±50.0 °C at 760 mmHg

311.3±30.1 °C

1.560

DMSO: ≥19mg/mL

Refrigerator

D +83° (chloroform)

229.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

I

6.1(a)

UN 2811 6.1/PG 2

3

28-63

22-25-28-36/37/39-45

TU3831000

T+

Missing Phrase - N15.00950417-P280

H300-H361

Toxicity

Side effects may include acne-like eruptions, burning, dryness, excessive hair growth, infection of the skin, irritation, itching, lack of skin colour, prickly heat, skin inflammation, skin loss or softening, stretch marks.

Drug Information

A topical anti-inflammatory product for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.|FDA Label

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.

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)|Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)|A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)

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.

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.

Acetonide 21-Acetate, Fluocinolone

Fluocinonide Use and Manufacturing

Uses

Glucocorticoid; anti-inflammatory.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:494.5
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:4
Exact Mass:494.21160968
Monoisotopic Mass:494.21160968
Topological Polar Surface Area:99.1
Heavy Atom Count:35
Complexity:1070
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Adrenal cortical hormones have anti-inflammatory and anti-allergic effects, can inhibit the proliferation of connective tissue, reduce the permeability of capillaries and cell membranes, reduce inflammatory exudates, and inhibit the formation and release of histamine and other inflammatory mediators.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Registered Holders

  • FARMABIOS S.P.A.

    Italy Italy
    Active
  • TAPI NL B.V.

    France France
    Active
  • Taipei (Beijing) Pharmaceutical Technology Co., Ltd.

    China China
    Active

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