14484-47-0 Usage
Description
Deflazacort, also known as Emflaza, is a glucocorticoid used as an anti-inflammatory and immunosuppressant. It belongs to a group of medicines called corticosteroids and is sometimes referred to as an oral steroid. Deflazacort is an inactive prodrug that is rapidly metabolized to the active drug 21-desacetyldeflazacort. It is used to treat a wide variety of conditions, including autoimmune diseases, joint and muscle diseases, allergies, and asthma.
Uses
Used in Pharmaceutical Industry:
Deflazacort is used as an anti-inflammatory and immunosuppressant for the treatment of various conditions such as autoimmune diseases (e.g., systemic lupus erythematosus, autoimmune hepatitis, sarcoidosis), joint and muscle diseases (e.g., rheumatoid arthritis), and allergies and asthma.
Used in Rheumatology:
Deflazacort is used as an antirheumatic agent for the treatment of rheumatoid arthritis. Its antirheumatic potency is similar to that of prednisone, while its hyperglycemic and calcium-depleting effects are reportedly less.
Used in Corticosteroid Therapy:
Deflazacort is used as a third-generation corticosteroid for the treatment of primary and secondary adrenocortical insufficiency, rheumatism, collagen diseases, skin diseases, allergic diseases, eye diseases, fulminant disseminated tuberculosis, hematopoietic system disorders, ulcerative colitis, idiopathic nephrotic syndrome, and other hematopoietic malignancies.
Used in Research:
Deflazacort-d3 is the labeled analogue of Deflazacort, used for research purposes in the study of its effects and mechanisms of action, particularly in the context of rheumatoid arthritis and lupus.
Adverse effects
Deflazacort carries the risks common to all corticosteroids, including immune suppression, decreased bone density, and endocrine insufficiency. In clinical trials, the most common side effects (>10% above placebo) were Cushing's-like appearance, weight gain, and
increased appetite.
Long-term medication can affect the normal growth of children, induced peptic ulcer perforation, which can cause euphoria, depression, insomnia and other psychiatric symptoms. Sudden withdrawal after long-term use can cause secondary adrenal insufficiency withdrawal reactions, which should gradually decrease until disabled.
Precautions
Like other glucocorticoids, it is general contraindicated in systemic infections.
Used with caution in diverticulitis, recent gastrointestinal surgery, renal failure, hypertension, diabetes, osteoporosis, myasthenia gravis embolism. Pregnancy and lactation women should used with caution.
Drug interactions
Cardiff may have unique row potassium, and it should pay more attention when combined with diuretics.
When combined with the drug having enzymatic action (rifampicin, phenobarbital, etc.), the corticosteroids should be properly increment.
Erythromycin, estrogen can inhibit the activity of this product and the metabolism, when combined with appropriate reductions.
Drug interactions
Potentially hazardous interactions with other drugsAldesleukin: avoid concomitant useAntibacterials: metabolism accelerated by rifamycins;
metabolism possibly inhibited by erythromycin;
concentration of isoniazid possibly reduced.Anticoagulants: efficacy of coumarins and
phenindione may be altered.Antiepileptics: metabolism accelerated by
carbamazepine, fosphenytoin, phenobarbital,
phenytoin and primidoneAntifungals: increased risk of hypokalaemia with
amphotericin - avoid; metabolism possibly inhibited
by itraconazole and ketoconazoleAntivirals: concentration possibly increased by
ritonavir.Ciclosporin: rare reports of convulsions in patients
on ciclosporin and high-dose corticosteroids;
increased half-life of deflazacort.Cobicistat: concentration increased by cobicistat -
avoid.Diuretics: enhanced hypokalaemic effects of
acetazolamide, loop diuretics and thiazide diuretics.Vaccines: high dose corticosteroids can impair
immune response to vaccines; avoid with live
vaccines.
Preparation
Compound 10g (1) was dissolved in 350ml methanol, and then added 8.3g of semicarbazide hydrochloride and 5.75ml of pyridine in 50ml of water, after the reaction. We can obtain compound 11g (Ⅱ). Compound 9g (Ⅱ) was dissolved 230ml 95% ethanol, the solution was added 3.6g of potassium carbonate and 2.34g of sodium borohydride in 36ml of water, which was refluxed for 30min and then added 2.34g of sodium borohydride. After the reaction, we can obtain compound 8.5g (Ⅲ). Compound 7.7g (Ⅲ) was dissolved in 154ml 10% hydrochloric acid in methanol, refluxed for 1h, to give Compound 6g (Ⅳ). Compound 12.5g (Ⅳ) was dissolved in 500ml of anhydrous toluene and 90ml of cyclohexanone. It was added 6.24g triisopropyl aluminum, 9g obtained by reacting the compound (V). 6.5g compound (V) was dissolved in 123ml dry dioxane, and 25% hydrogen bromide in acetic acid solution is heated, and then added 5.5g of bromine in dioxane; the reaction solution was poured into the water, collected by filtration after the crystals were carefully dried, redissolved in dimethylformamide. It? was added 7.5g of lithium bromide and lithium carbonate (1: 2) mixture. After heating the reaction, we can obtain the compound 5.1g (ⅵ). 2g compound (Ⅵ) was dissolved in tetrahydrofuran-methanol (1: 1), added to 3.9g calcium oxide and 0.1g of azobisisobutyronitrile. It was added 2g of iodine in tetrahydrofuran-methanol mixture; After the reaction was filtered off precipitate , which was dissolved in acetone,? it was then added triethylamine 20ml, 20ml and 12ml acetone, acetic acid, atter the reaction, we can obtain 1.6g deflazacort.
References
https://en.wikipedia.org/wiki/Deflazacort
http://patient.info/medicine/deflazacort-tablets-calcort
Originator
Dow Lepetit (Italy)
Biochem/physiol Actions
Deflazacort is an anti-inflammatory and immunosuppressant glucocorticoid.
Clinical Use
Glucocorticoid:Suppression of inflammatory and allergic disorders
Metabolism
Deflazacort is immediately converted by plasma
esterases to the pharmacologically active metabolite (D
21-OH). It is 40% protein-bound and has no affinity for
corticosteroid-binding-globulin (transcortin). Elimination
takes place primarily through the kidneys; 70% of the
administered dose is excreted in the urine. The remaining
30% is eliminated in the faeces. Metabolism of D 21-OH
is extensive; only 18% of urinary excretion represents
D 21-OH. The metabolite of D 21-OH, deflazacort
6-beta-OH, represents one third of the urinary
elimination.
Check Digit Verification of cas no
The CAS Registry Mumber 14484-47-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,4,8 and 4 respectively; the second part has 2 digits, 4 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 14484-47:
(7*1)+(6*4)+(5*4)+(4*8)+(3*4)+(2*4)+(1*7)=110
110 % 10 = 0
So 14484-47-0 is a valid CAS Registry Number.
InChI:InChI=1/C23H29NO4/c1-12(25)23-19(28-13(2)24-23)10-17-16-6-5-14-9-15(26)7-8-21(14,3)20(16)18(27)11-22(17,23)4/h7-9,16-20,27H,5-6,10-11H2,1-4H3/t16-,17-,18-,19+,20+,21-,22-,23?/m0/s1
14484-47-0Relevant articles and documents
Expeditious synthesis and preliminary antimicrobial activity of deflazacort and its precursors
, ()
The synthesis of deflazacort (DFZ) and a preliminary evaluation of its microbial activity against the human pathogens Acinetobacter baumannii and Staphylococcus aureus is herein reported. While DFZ is inactive, one of its synthetic precursors showed a strong antibacterial activity against both Gram-negative and -positive bacteria.
New process for reducing steroid 11-ketone group
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Paragraph 0117; 0118; 0119; 0120; 0121; 0122, (2016/10/09)
The invention discloses a method for preparing a steroid 11 beta-hydroxyl compound by reducing a steroid 11-ketone group compound. The method comprises that the steroid 11-ketone group compound and a reduction agent are subjected to a reaction in a non-ester solvent to obtain the steroid 11 beta-hydroxyl compound; the reduction agent is selected from one or more of sodium borohydride, potassium borohydride and lithium borohydride; a metal salt is also added in the reaction system and is selected from one or more of a divalent calcium salt, a divalent magnesium salt, a divalent zinc salt, a divalent copper salt, a divalent cobalt salt, a divalent chromium salt, a tetravalent titanium salt and a trivalent cerium salt; the non-ester solvent is a protic solvent or a mixed solvent of other non-ester organic solvents and the protic solvent. The method has the greatest advantages that the high-purity 11 beta-hydroxyl compound is obtained with high yield at room temperature, and the method is simple in operation, good in repeatability, and easy to industrialize.
Preparation of (11 beta ,16 beta )-21-(acetyloxy)-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione
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, (2008/06/13)
PCT No. PCT/EP96/05390 Sec. 371 Date Jun. 5, 1998 Sec. 102(e) Date Jun. 5, 1998 PCT Filed Dec. 4, 1996 PCT Pub. No. WO97/21722 PCT Pub. Date Jun. 19, 1997A process for preparing the compound (11 beta ,16 beta )-21-(acetyloxy)-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (INN deflazacort) which comprises reacting (11 beta ,16 beta )-11,21 -dihydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione with acetic anhydride in a suitable organic solvent in the presence of a basic catalyst and water.
