Deflazacort

Iupac Name：[2-[(1S,2S,4R,8S,9S,11S,12S,13R)-11-hydroxy-6,9,13-trimethyl-16-oxo-5-oxa-7-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-6,14,17-trien-8-yl]-2-oxoethyl] acetate

CAS No.: 14484-47-0

Molecular Weight：441.52

Modify Date.: 2022-11-25 02:23

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Deflazacort
1.2 Synonyms: (11b,16b)-21-(Acetyloxy)-11-hydroxy-2'-methyl-5'H-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione (5'β)-11β-Hydroxy-21-acetyloxy-2'-methyl-1,2,4,5-tetradehydropregnano[17,16-d]oxazole-3,20-dione (5'β)-21-Acetyloxy-11β-hydroxy-2'-methylpregnano[17,16-d]oxazole-1,4-diene-3,20-dione 11b,21-Dihydroxy-2'- 11b,21-Dihydroxy-2'-methyl-5'bH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione 21-acetate 16-d)oxazole-3,20-dione,11-beta,21-dihydroxy-2’-5’-beta-h-pregna-4-dieno(17 2-[(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-5-Hydroxy-4a,6a,8-trimethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]oxazol-6b-yl]-2-oxoethyl acetate 2H-Naphth[2',1':4,5]indeno[1,2-d]oxazol-2-one, 6b-[2-(acetyloxy)acetyl]-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-5-hydroxy-4a,6a,8-trimethyl-, (4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)- azacort calcort Cortax,Decortil,Deflanil deflan Denazacort Dezacor DL 458-IT EINECS 238-483-7 Flantadin Lantadin Pregna-1,4-diene-11b,21-diol-3,20-dione[17a,16a-d]-2'-methyloxazoline 21-Acetate

1.3 CAS No.: 14484-47-0

1.4 CID: 189821

1.5 EINECS(EC#): 238-483-7

1.6 Molecular Formula: C25H31NO6 (isomer)

1.7 Inchi: InChI=1S/C25H31NO6/c1-13-26-25(20(30)12-31-14(2)27)21(32-13)10-18-17-6-5-15-9-16(28)7-8-23(15,3)22(17)19(29)11-24(18,25)4/h7-9,17-19,21-22,29H,5-6,10-12H2,1-4H3/t17-,18-,19-,21+,22+,23-,24-,25+/m0/s1

1.8 InChkey: FBHSPRKOSMHSIF-GRMWVWQJSA-N

1.9 Canonical Smiles: CC1=NC2(C(O1)CC3C2(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)C(=O)COC(=O)C

1.10 Isomers 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

2. Properties

2.1 Density: 1.41

2.1 Melting point: 255-256.5°C

2.1 Boiling point: 544.2 °C at 760 mmHg

2.1 Refractive index: 1.675

2.1 Flash Point: 282.9 °C

2.1 Precise Quality: 383.21000

2.1 PSA: 75.96000

2.1 logP: 2.45560

2.1 Solubility: DMSO: ≥20mg/mL

2.2 Appearance: COA

2.3 Color/Form: Powder

2.4 pKa: 14.30±0.70(Predicted)

2.5 Water Solubility: DMSO: ≥20mg/mL

2.6 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Usage: A systemic corticosteroid. A derivative of prednisolone. Used for rheumatoid arthritis and lupus

4. Safety and Handling

4.1 Risk Statements: 24/25

4.1 Safety Statements: 24/25

4.1 Hazard Declaration: H360

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P201, P202, P260, P281, P308+P313, P314, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: TU4157050

4.1 Toxicity: LD50 orally in mice: 5200 mg/kg (Schiatti)

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 1A

Specific target organ toxicity \u2013 repeated exposure, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H360 May damage fertility or the unborn child H373 May cause damage to organs through prolonged or repeated exposure
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention. P314 Get medical advice/attention if you feel unwell.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

14484-47-0Total: 11 Synthesis Route

19890-71-2

14484-47-0 276 Suppliers

Literatures:
Steroids, , vol. 13, p. 383 - 397
Yield: null

16119-56-5

14484-47-0 276 Suppliers

Literatures:
Steroids, , vol. 13, p. 383 - 397
Yield: null

19890-70-1

14484-47-0 276 Suppliers

Literatures:
Steroids, , vol. 13, p. 383 - 397
Yield: null

View all

8. Precursor and Product

precursor:

16119-50-9

13649-85-9

16119-56-5

13649-88-2

14927-19-6

19890-69-8

13649-86-0

19890-71-2

13649-87-1

19890-68-7

19890-70-1

product :

13649-57-5

9. Other Information

9.0 Dissociation Constants: 5.52

9.1 Mesh: Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)|Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

9.2 Absorption: Deflazacort is rapidly absorbed after oral administration with peak concentration occurring within 1-2 hours. One pharmacokinetic study determined an AUC (area under the curve) of 280 ng/ml · h. The bioavailability of both the oral suspension and tablet are similar. In clinical studies, coadministration of deflazacort crushed with food or applesauce did not affect absorption or bioavailability.|Urinary excretion is the major route of deflazacort elimination, accounting for about about 70% of the excreted dose. The remainder of the dose (about 30%) is excreted in the feces. Elimination is almost completed by 24 hours post-dose. 21-deflazacort makes up about 18% of the eliminated drug in the urine.|One study determined the volume of distribution to be 204 ± 84 L.|114 ±27 L/h, according to one noncompartmental pharmacokinetic study. The clearance of corticosteroids is enhanced in hypothyroid patients and increased in patients with hyperthyroidism. Dosing adjustments may be considered according to thyroid status. A study of corticosteroid clearance was performed in patients with a creatinine clearance of 15 mL/min or less, and determined that the active metabolite of deflazacort, 21-deflazacort was similar to that in patients with normal renal clearance.

9.3 Metabolism: After oral ingestion, deflazacort is deacetylated at position 21 by plasma esterases, producing the active metabolite 21-deflazacort. 21-deflazacort is then further metabolized by CYP3A4 to inactive metabolite products. Deflazacort 21-OH metabolism is extensive. The metabolite of deflazacort-21-OH is deflazacort 6-beta-OH.

9.4 Biological Half Life: The half-life of deflazacort ranges from 1.1 to 1.9 h

9.5 Mesh Entry Terms: Calcort

9.6 Use Classification: Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9.7 Merck: 14,2862

9.8 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.

9.9 Application: The third generation of corticosteroids, anti-inflammatory, anti-allergy, increased gluconeogenesis and so on. For the use of the primary and secondary adrenocortical insufficiency, rheumatism, collagen diseases, skin diseases, allergic diseases, eye diseases, and fulminant disseminated tuberculosis, hematopoietic system disorders, ulcerative colitis, idiopathic nephrotic syndrome, and other hematopoietic malignancies.

9.10 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.

9.11 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.

9.12 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.

9.13 References: https://en.wikipedia.org/wiki/Deflazacort
http://patient.info/medicine/deflazacort-tablets-calcort

9.14 Chemical Properties: Off-White to Pale Yellow Solid

9.15 Uses: antiinflammatory

9.16 Uses: A systemic corticosteroid. A derivative of prednisolone. Used for rheumatoid arthritis and lupus

9.17 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.

9.18 Description: 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.

9.19 Originator: Dow Lepetit (Italy)

9.20 Uses: Deflazacort-d3, is the labeled analogue of Deflazacort (D228975), a systemic corticosteroid, and a derivative of prednisolone. Used for rheumatoid arthritis and lupus.

9.21 Brand name: LANTADIN; DEFLAN

9.22 Biochem/physiol Actions: Deflazacort is an anti-inflammatory and immunosuppressant glucocorticoid.

10. Computational chemical data

Molecular Weight: 441.52g/mol
Molecular Formula: C₂₅H₃₁NO₆
Compound Is Canonicalized: True
XLogP3-AA: 2
Exact Mass: 441.21513771
Monoisotopic Mass: 441.21513771
Complexity: 996
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 7
Topological Polar Surface Area: 102
Heavy Atom Count: 32
Defined Atom Stereocenter Count: 8
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB6OAAAAAAAAAAAAAAAAAAAAYIAAAAwYIAAAAAQAGDAAAAAHgAACAAAD5yhgAICCAIABgCoAqDyDAIAAAAgAAAICAHQAEgCEBYAgQQDQAAGoAAIAYP4/P3PgAAAAAAAAADAAAYAADAAAaAADQgAAA==

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