2135-17-3 Usage
Description
Flumethasone is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic, and vasoconstrictive properties. It functions as an agonist of glucocorticoid and mineralocorticoid receptors, exhibiting significant anti-inflammatory activity. Flumethasone is a white solid that is insoluble in water, and its mechanism of action involves inhibiting arachidonic acid's role in the biosynthesis of prostaglandins and leukotrienes.
Used in Veterinary Practice:
Flumethasone is used as an anti-inflammatory glucocorticoid for a variety of animals, helping to combat inflammatory symptoms caused by pathogens and aiding in the understanding of inflammatory mechanisms. It is also utilized to investigate novel techniques for detecting and quantifying steroid compounds within muscles.
Used in Skin Condition Treatment:
Flumethasone is used as a topical anti-inflammatory corticosteroid for the treatment of various skin conditions, including contact dermatitis, atopic dermatitis, eczema, psoriasis, diaper rash, bug bites, and other inflammation-related skin disorders.
Used in Otitis Externa and Otomycosis Treatment:
In combination with Clioquinol, Flumethasone is used as a corticosteroid for the treatment of otitis externa and otomycosis, showing a potency 420 times that of cortisone in an animal model for anti-inflammatory activity.
Used in Cortisol Assays:
Flumethasone pivalate, a topical difluorinated corticosteroid ester, is used in cortisol assays to study early porcine conceptus development, providing insights into the role of corticosteroids in early embryonic development.
Used in Cardiac Regeneration Research:
Flumethasone has been shown to impair cell cycle re-entry of cardiac cells and cardiac regeneration in zebrafish, indicating its potential use in research related to cardiac regeneration and the study of the effects of corticosteroids on heart tissue recovery post-injury.
Biological Activity
Flumethasone pivalate is a glucocorticoid receptor agonist used in studies on plasma transcortin binding. It binds to the nucleus causing a variety of genetic activations and repressions. The anti-inflammatory action of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system 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.
Originator
Locacorten,Ciba,W. Germany,1964
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.
Therapeutic Function
Glucocorticoid, Antiinflammatory
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.
Check Digit Verification of cas no
The CAS Registry Mumber 2135-17-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,1,3 and 5 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2135-17:
(6*2)+(5*1)+(4*3)+(3*5)+(2*1)+(1*7)=53
53 % 10 = 3
So 2135-17-3 is a valid CAS Registry Number.
InChI:InChI=1/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13?,14?,16+,17+,19+,20+,21+,22+/m1/s1
2135-17-3Relevant articles and documents
Synthesis method of steroid corticosteroid 21-hydroxyl side chain
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Paragraph 0042-0044, (2020/03/06)
The invention belongs to the technical field of steroid hormone preparation, and particularly relates to a synthesis method of a steroid corticosteroid 21-hydroxyl side chain. The synthesis method comprises the step that a compound I reacts with a peroxide to obtain a compound II. The reaction route is as follows. (Please see the specification for the reaction route.) According to the synthesis method, the 21-hydroxysteroid compound is obtained from a 20-alkenyl steroid compound substrate by a one-pot method. Compared with a previous construction method, the step is the shortest, conditions are simpler, and the highest efficiency is achieved.
Ring opening and fluoridation method and device of steroidal epoxy compound
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Paragraph 0038; 0039; 0041, (2017/07/22)
The invention discloses a method of preparing a compound II, which is as shown as the following reaction formula as shown in the specification. A 9 alpha-fluorine-11 beta -hydroxyl steroidal compound II is prepared via epoxy compound ring opening and fluoridation of a steroidal epoxy compound I by taking hydrogen fluoride as a fluorination reagent in a solvent consisting of arene and water. In the formula, R is CH3, CH2OH or CH2OAc; R1 is OH; R2 is alpha-CH3 or beta-CH3; and R3 is F or H. A continuous reaction device as shown in Figure 1 can be used in the method.
Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
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, (2008/06/13)
Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.
