127-31-1 Usage
Uses
Used in Pharmaceutical Industry:
Fludrocortisone is used as a medication for adrenal insufficiency, a condition where the adrenal glands do not produce enough hormones. It helps to replace the missing hormone aldosterone, which is responsible for maintaining the balance of sodium and potassium in the body.
Used in Electrolyte Regulation:
Fludrocortisone is used as an electrolyte-regulating agent to manage conditions where there is an imbalance of sodium and potassium levels in the body. This can occur due to various reasons, such as certain diseases, medications, or dietary factors.
Used in Autoimmune Diseases:
In some cases, Fludrocortisone is used as an adjunct therapy for autoimmune diseases, such as systemic lupus erythematosus, where it can help to reduce inflammation and manage symptoms.
Used in Orthostatic Hypotension:
Fludrocortisone is used as a treatment for orthostatic hypotension, a condition where blood pressure drops significantly upon standing, causing dizziness or fainting. It helps to increase blood volume and improve blood pressure regulation.
Overall, Fludrocortisone is a versatile medication with various applications in the pharmaceutical industry, primarily focusing on hormone replacement, electrolyte regulation, and managing symptoms of certain diseases.
Originator
Alflorone Acetate,MSD,US,1954
Manufacturing Process
Hydrocortisone acetate is first reacted with phosphorus oxychloride in pyridine
to give the corresponding olefin. Then a sequence consisting of hypobromous
acid addition, ring closure to the epoxide and ring opening with hydrogen
fluoride gives fludrocortisone acetate. Preparation of a crystalline product is
described then in US Patent 2,957,013.
Therapeutic Function
9-Fluoro-11β,17,21-trihydroxy-pregn-4-ene-3,20-dione
acetate
Clinical Use
Fludrocortisone acetate is used
orally for mineralocorticoid replacement therapy in patients with adrenocortical insufficiency, such as Addison's
disease. This drug, introduced in 1954, helped to provide the impetus for the synthesis and biological
evaluation of newer halogenated analogues.
Synthesis
Fludrocortisone, 9α-fluoro-11β,17α,21-trihydroxypregn-4-en-3,20-
dione (27.2.14), is synthesized from hydrocortisone acetate (27.1.17). In the first stage of
synthesis, dehydration of the hydrocortisone molecules is accomplished using phosphorous
chloride in pyridine, which forms a product with a double bond at C9–C11 27.2.11. The
resulting double bond is synthesized into an epoxide by an initial transformation to a bromohydrine
using N-bromoacetamide and subsequent dehydrobromination using sodium
acetate, which forms 21-O-acetoxy-9d-11β-epoxy-17α-hydroxy-4-pregnen-3,20-dione
(27.2.12). As described above, the epoxide ring is opened by hydrofluoric acid, which results
in the formation of the 21-O-acetate of fludrocortisone 27.2.13. Hydrolysis of the acetyl
group of Fludrocortisone using potassium acetate gives fludrocortisone (27.2.14).
Check Digit Verification of cas no
The CAS Registry Mumber 127-31-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 7 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 127-31:
(5*1)+(4*2)+(3*7)+(2*3)+(1*1)=41
41 % 10 = 1
So 127-31-1 is a valid CAS Registry Number.
InChI:InChI=1/C23H31FO6/c1-13(25)30-12-19(28)22(29)9-7-16-17-5-4-14-10-15(26)6-8-20(14,2)23(17,24)18(27)11-21(16,22)3/h10,16-18,27,29H,4-9,11-12H2,1-3H3/t16?,17?,18-,20-,21-,22-,23-/m0/s1
127-31-1Relevant academic research and scientific papers
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.
Cytotoxic nucleoside-corticosteroid phosphodiesters
-
, (2008/06/13)
Nucleotides of nucleosides or bases having known cytotoxic activity are reacted with steroids, preferably corticosteroids, to form corresponding cytotoxic nucleoside-corticosteroid phosphodiester analogues of the formula: STR1 wherein: steroid is the residue formed by removal of a hydroxyl hydrogen atom from a natural or synthetic adrenal corticosteroid containing the characteristic cyclopentanophenanthrene nucleus which is esterified to the phosphate moiety at the 21-position; sugar is a naturally occurring pentose or deoxypentose in the furanose form, preferably ribose, deoxyribose, lyxose, xylose or arabinose and especially ribose, deoxyribose or arabinose, which is esterified to the phosphate moiety at the 5'-position and covalently bonded to the heterocycle moiety at the 1'-position to form a nucleoside; and heterocycle is a purine, pyrimidine, hydrogenated pyrimidine, triazolopurine or similar nucleoside base. The conjugates exhibit an enhanced therapeutic index as compared to the parent nucleoside or base compounds, and are thus useful cytotoxic, antiviral and antineoplastic agents.
