Originator
Locacorten,Ciba,W. Germany,1964
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.
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.
References
[1] CLAUDIA GROSSMANN. Transactivation via the human glucocorticoid and mineralocorticoid receptor by therapeutically used steroids in CV-1 cells: a comparison of their glucocorticoid and mineralocorticoid properties.[J]. European Journal of Endocrinology, 2004, 151 3: 397-406. DOI:
10.1530/eje.0.1510397[2] HITOSHI ISHIGURO. Differential regulation of bladder cancer growth by various glucocorticoids: corticosterone and prednisone inhibit cell invasion without promoting cell proliferation or reducing cisplatin cytotoxicity.[J]. Cancer Chemotherapy and Pharmacology, 2014, 74 2: 249-255. DOI:
10.1007/s00280-014-2496-7[3] DARIUSZ BEDNAREK . The effect of steroidal and non-steroidal anti-inflammatory drugs on the cellular immunity of calves with experimentally-induced local lung inflammation[J]. Veterinary immunology and immunopathology, 1999, 71 1: Pages 1-15. DOI:
10.1016/s0165-2427(99)00076-8[4] ANNE-SOPHIE DE PREUX CHARLES. Distinct effects of inflammation on preconditioning and regeneration of the adult zebrafish heart.[J]. Open Biology, 2016, 6 7. DOI:
10.1098/rsob.160102
