2135-17-3 Usage
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
-
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.
A 17, 21 - double-hydroxy steroid derivatives of synthetic method
-
, (2018/04/02)
The invention relates to a method of preparing 17, 21-double-hydroxyl steroid derivatives by using 6, 9-substituted silyl steroid enol ether compound I as an initiator.
Ring opening and fluoridation method and device of steroidal epoxy compound
-
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.
PROCESS FOR THE PREPARATION OF 17-DESOXY-CORTICOSTEROIDS
-
Page/Page column 20, (2012/02/05)
The present invention provides an improved process for the preparation of 17-desoxy corticosteroid derivatives in a single chemical step by reacting the 17-hydroxy starting material with an excess of Trimethylsilyl Iodide. The present invention is specifically advantageous in preparing 17-desoxy corticosteroid derivatives having one or more halogen groups at positions 2, 6, 7 or 9 of the corticosteroid such as Clocortolone or Desoximetasone.
Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor
-
, (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.
Application of Curvularia sp to the hydrolysis of steroid pivalates
Kruszewska,Chmielowiec,Uszycka-Horawa
, p. 809 - 810 (2007/10/03)
As glucocorticoids have alkali - sensitive hydroxyacetylic side chain, conventional methods of removing of 21 - pivalates groups are risky. In this paper we described the hydrolysis of pivalates of some glucocorticoids by fungi imperfecti: Curvularia lunata, Curvularia tuberculata, Cylindrocladium simplex Meyer and Cunninghamella elegans. The highest yield of hydrolysis was found in the case of hydrocortisone and prednisolone pivalates with Curvularia lunata and Curvularia tuberculata. The other two tested enzymes gave in all studied cases null or extremely poor results.
Process and intermediates for the preparation of 17 alphahydroxyprogesterones and corticoids from an enol steroid
-
, (2008/06/13)
This invention discloses an improved process for the production of corticoids from 17α-hydroxy steroids utilizing peroxymonosulfate.
Water-soluble steroid compounds
-
, (2008/06/13)
Beta-cyclodextrin forms a water-soluble complex or inclusion compound with steroid compounds having a molecular structure smaller than the interior cavity in the doughnut-shaped molecular structure of beta-cyclodextrin. The resulting inclusion compounds can be used for a variety of applications including aqueous topical ophthalmic preparations and topical dermatological ointments.
17 Beta-thiocarboxylic acid esters of 4-halo-3-oxoandrost-4-enes
-
, (2008/06/13)
Certain 3-oxoandrost-4-ene and 3-oxoandrosta-1,4-diene 17 beta-thiocarboxylic acid esters substituted at the 4-position with a fluoro, chloro or bromo and optionally substituted at the six position with fluoro or chloro are useful as anti-inflammatory steroids. These compounds are optionally substituted at the 9 alpha position with fluoro, chloro or bromo; substituted at the 11 with a keto, a beta-hydroxy or a beta-chloro (the latter only when there is a 9 alpha-chloro); substituted at 16 alpha,-17 alpha-positions with isopropylidenedioxy; and substituted at 16 alpha (or 16 beta) with methyl or hydrogen when there is a 17 alpha-hydroxy (or an ester).
