Deflazacort

Base Information

• Chemical Name: Deflazacort
• CAS No.: 14484-47-0
• Deprecated CAS: 74712-90-6
• Molecular Formula: C25H31NO6
• Molecular Weight: 441.524
• Hs Code.: 29349990
• European Community (EC) Number: 238-483-7
• UNII: KR5YZ6AE4B
• DSSTox Substance ID: DTXSID9020378
• Nikkaji Number: J83.648F
• Wikipedia: Deflazacort
• Wikidata: Q779118
• NCI Thesaurus Code: C87230
• RXCUI: 22396
• Metabolomics Workbench ID: 153000
• ChEMBL ID: CHEMBL1201891
• Mol file: 14484-47-0.mol

Synonyms:Calcort;deflazacort;Dezacor;Emflaza;Zamene

Chemical Property of Deflazacort

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 4.13E-14mmHg at 25°C
• Melting Point: 255-256.5 °C
• Refractive Index: 1.675
• Boiling Point: 595.4 °C at 760 mmHg
• PKA: 14.30±0.70(Predicted)
• Flash Point: 313.9 °C
• PSA: 102.26000
• Density: 1.41 g/cm³
• LogP: 1.99880
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 441.21513771
• Heavy Atom Count: 32
• Complexity: 996

Purity/Quality:

99.00% ^*data from raw suppliers

Deflazacort-d3 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2(C(O1)CC3C2(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)C(=O)COC(=O)C
• Isomeric SMILES: CC1=N[C@@]2([C@H](O1)C[C@@H]3[C@@]2(C[C@@H]([C@H]4[C@H]3CCC5=CC(=O)C=C[C@]45C)O)C)C(=O)COC(=O)C
• Recent ClinicalTrials: Deflazacort vs. Prednisolone in Acute-stage ABPA
• Recent EU Clinical Trials: Deflazacort TREATment in LMNA related congenital muscular dystrophy: study of clinical effectiveness and search for reliable biomarkers.
• Description: Deflazacort (trade name Emflaza among others) is a glucocorticoid used as an anti-inflammatory and immunosuppressant. It belongs to a group of medicines called corticosteroids. It is sometimes referred to simply as an oral steroid. Deflazacort is an inactive prodrug which is metabolized rapidly to the active drug 21-desacetyldeflazacort.It is used to treat a wide variety of conditions. Some examples include autoimmune diseases (for example, systemic lupus erythematosus (SLE), autoimmune hepatitis, sarcoidosis), joint and muscle diseases (for example, rheumatoid arthritis), and allergies and asthma. Cardiff can be specially designed for the third generation of corticosteroids, anti-inflammatory, anti-allergy, and it increased gluconeogenesis and so on. It acts as prednisolone 10~20 times of the dragon, 40 times as hydrocortisone. This product has no mutagenic effect. This product, labeled with C14 study, shows that the product of the gastrointestinal tract rapidly absorbed, reaching the peak blood concentration after 1~2h, forming the active substance by hydrolysis, and the latter further metabolic processes is similar with other corticosteroids, as well as the active metabolite T1/2 is 2 h and the rats are mainly distributed in the kidney and hematopoietic system and other organizations. Figure 1 is a deflazacort formula. Deflazacort is an antiinflammatory treatment of rheumatoid arthritis. Its antirheumatic potency i s similar to that of prednisone, while its hyperglycernic and calcium depleting effects are reportedly less.
• 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. 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.
• Uses: Deflazacort-d3, is the labeled analogue of Deflazacort (D228975), a systemic corticosteroid, and a derivative of prednisolone. Used for rheumatoid arthritis and lupus. antiinflammatory A systemic corticosteroid. A derivative of prednisolone. Used for rheumatoid arthritis and lupus
• Clinical Use: Glucocorticoid:Suppression of inflammatory and allergic disorders

Technology Process of Deflazacort

There total 34 articles about Deflazacort which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

C28H37N3O7 → deflazacort (14484-47-0)

Guidance literature:

With hydrogenchloride; water; In acetone; at 20 ℃; for 24h;

DOI:10.1039/c9ra03673c

Reference yield:

21-Deacetyldeflazacort (13649-57-5,94158-00-6) + acetyl chloride (75-36-5) → deflazacort (14484-47-0)

Guidance literature:

With pyridine; In chloroform; at 40 - 45 ℃; for 2h; Green chemistry;

Reference yield:

acetic anhydride (108-24-7) + 21-Deacetyldeflazacort (13649-57-5,94158-00-6) → deflazacort (14484-47-0)

Guidance literature:

With toluene-4-sulfonic acid; at 40 - 45 ℃; for 2h; Temperature; Green chemistry;

upstream raw materials:

21-Acetoxy-3.11.20-trioxo-Δ^1.4-pregnadien[17α.16α-d](2'-methyl-oxazolin)

21-acetoxy-2'-methyl-(16β)-pregna-1,4,9(11)-trieno[17,16-d]oxazole-3,20-dione

acetic acid

3β-hydroxy-2'-methyl-(5α,16β)-pregn-9(11)-eno[17,16-d]oxazol-20-one

Downstream raw materials:

21-Deacetyldeflazacort

21-acetoxy-2'-methyl-(16β)-pregna-1,4,9(11)-trieno[17,16-d]oxazole-3,20-dione

Refernces

• 1、 -. "Preparation method of deflazacort". . . Retrieved 2017/08/27.
• 2、 -. "Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor". . . Retrieved 2008/06/13.