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HomeProduct name listFlumethasone

Flumethasone

Synonym(s):6α,9α-Difluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione;6α,9α-Difluoro-16α-methylprednisolone;6α-Fluorodexamethasone

  • CAS NO.:2135-17-3
  • Empirical Formula: C22H28F2O5
  • Molecular Weight: 410.45
  • MDL number: MFCD00056464
  • EINECS: 218-370-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-21 15:02:05
Flumethasone Structural

What is Flumethasone?

Absorption

Minimal if applied topically

Toxicity

Can lead to signs of irritation such as burning sensation, itching or skin rash at the site of application; hypersensitivity reactions.

Description

Flumethasone is an agonist of glucocorticoid and mineralocorticoid receptors with EC50 values of 0.26 and 0.494 nM, respectively, in CV-1 cells expressing human receptors. In vitro, it inhibits the growth of UM-UC-3, TCC-SUP, and 5637 urothelial carcinoma cell lines at a concentration of 100 nM. Flumethasone (5 mg per animal) decreases tumor necrosis factor (TNF) production ex vivo in blood cells collected by bronchoalveolar lavage (BAL) from calves with experimentally-induced local lung inflammation. It also inhibits phytohemagglutinin-induced delayed hypersensitivity in calf skin. In vivo, flumethasone (5 μM) impairs cell cycle re-entry of cardiac cells seven days post cryo-injury to the heart and impairs cardiac regeneration in zebrafish.

Chemical properties

White Solid

Originator

Locacorten,Ciba,W. Germany,1964

The Uses of Flumethasone

A glucocorticoid. An anti-inflammatory

The Uses of Flumethasone

topical anti-inflammatory corticosteroid

The Uses of Flumethasone

A glucocorticoid. An anti-inflammatory.

Background

Flumethasone is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.

What are the applications of Application

Flumethasone is A glucocorticoid. An anti-inflammatory.

Indications

For the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin conditions

Definition

ChEBI: Flumethasone is a fluorinated steroid, a glucocorticoid, an 11beta-hydroxy steroid, a 17alpha-hydroxy steroid, a 21-hydroxy steroid, a 20-oxo steroid, a 3-oxo-Delta(1),Delta(4)-steroid, a primary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It has a role as an anti-inflammatory drug. It derives from a hydride of a pregnane.

Manufacturing Process

To approximately 1.3 g of hydrogen fluoride contained in a polyethylene bottle and maintained at -60°C was added 2.3 ml of tetrahydrofuran and then a solution of 500 mg (0.0012 mol) of 6α-fluoro-9β,11β-epoxy-16α-methyl- 17α,21-dihydroxy-1,4-pregnadiene-3,20-dione-21-acetate in 2 ml of methylenechloride. The steroid solution was rinsed in with an additional 1 ml of methylene chloride. The light red colored solution was then kept at approximately -30°C for 1 hour and at -10°C for 2 hours. At the end of this period it was mixed cautiously with an excess of cold sodium bicarbonate solution and the organic material extracted with the aid of additional methylene chloride. The combined extracts were washed with water, dried over anhydrous sodium sulfate and concentrated to approximately 35 ml. The solution was chromatographed over 130 g of Florisil anhydrous magnesium silicate. The column was developed with 260 ml portions of hexanes (Skellysolve B) containing increasing proportions of acetone. There was thus eluted 6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methyl-1,4-pregnadiene- 3,20-dione 21-acetate which was freed of solvent by evaporation of the eluate fractions.

brand name

Locorten (Novartis).

Therapeutic Function

Glucocorticoid, Antiinflammatory

Pharmacokinetics

Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.

Veterinary Drugs and Treatments

Flumethasone injection (Flucort?) is labeled in horses as indicated for: 1) Musculoskeletal conditions due to inflammation, where permanent structural changes do not exist, such as bursitis, carpitis, osselets and myositis. Following therapy an appropriate period of rest should be instituted to allow a more normal return to function of the affected part. 2) In allergic states such as hives, urticaria and insect bites.
Flumethasone injection (Flucort?) is labeled in dogs as indicated for: 1) Musculoskeletal conditions due to inflammation of muscles or joints and accessory structures, where permanent structural changes do not exist, such as arthritis, osteoarthritis, the disc syndrome and myositis. In septic arthritis appropriate antibacterial therapy should be concurrently administered. 2) In certain acute and chronic dermatoses of varying etiology to help control the pruritus, irritation and inflammation associated with these conditions. The drug has proven useful in otitis externa in conjunction with topical medication for similar reasons. 3) In allergic states such as hives, urticaria and insect bites. 4) Shock and shock-like states, by intravenous administration.
Flumethasone injection (Flucort?) is labeled in cats as indicated for certain acute and chronic dermatoses of varying etiology to help control the pruritus, irritation and inflammation associated with these conditions.
Glucocorticoids have been used in an attempt to treat practically every malady that afflicts man or animal, but there are three broad uses and dosage ranges for use of these agents. 1) Replacement of glucocorticoid activity in patients with adrenal insufficiency, 2) as an antiinflammatory agent, and 3) as an immunosuppressive. Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases (e.g., rheumatoid arthritis), collagen diseases (e.g., systemic lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic diseases (e.g., pemphigus, allergic dermatoses), hematologic disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias), neoplasias, nervous system disorders (increased CSF pressure), GI diseases (e.g., ulcerative colitis exacerbations), and renal diseases (e.g., nephrotic syndrome). Some glucocorticoids are used topically in the eye and skin for various conditions or are injected intra-articularly or intra-lesionally. The above listing is certainly not complete.

Metabolism

Primarily hepatic

Properties of Flumethasone

Melting point: 237-240°C
Boiling point: 569.8±50.0 °C(Predicted)
Density  1.1621 (estimate)
storage temp.  2-8°C
solubility  acetic acid: soluble10mg/mL
form  solid
pka 11.98±0.70(Predicted)
color  white
optical activity [α]25/D 67.0 to 71.0°, c = 1 in dioxane
Water Solubility  1mg/L(20 ºC)
Merck  14,4138
CAS DataBase Reference 2135-17-3(CAS DataBase Reference)

Safety information for Flumethasone

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H351:Carcinogenicity
Precautionary Statement Codes P281:Use personal protective equipment as required.

Computed Descriptors for Flumethasone

InChIKey WXURHACBFYSXBI-GQKYHHCASA-N

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