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: 2024-11-01 13:17:44
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) |
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 |
Abamectin manufacturer
Avik Pharmaceutical Limited
Symbiotec Pharma Lab Pvt Ltd
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