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Chemistry

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Also known as: 14484-47-0, Azacort, Calcort, Oxazacort, Flantadin, Emflaza
Molecular Formula
C25H31NO6
Molecular Weight
441.5  g/mol
InChI Key
FBHSPRKOSMHSIF-GRMWVWQJSA-N
FDA UNII
KR5YZ6AE4B

Deflazacort
Deflazacort is a synthetic glucocorticoid prodrug, with anti-inflammatory and immunomodulating properties. Upon administration, the active metabolite of deflazacort, 21-desacetyl deflazacort, binds to and activates tissue glucocorticoid receptors. This results in the inhibition of specific leukocyte functions and the inhibition of proinflammatory cytokine production.
Deflazacort is a Corticosteroid. The mechanism of action of deflazacort is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

Deflazacort

2 Identification
2.1 Computed Descriptors
2.1.1 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
2.1.2 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
2.1.3 InChI Key
FBHSPRKOSMHSIF-GRMWVWQJSA-N
2.1.4 Canonical SMILES
CC1=NC2(C(O1)CC3C2(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)C(=O)COC(=O)C
2.1.5 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
2.2 Other Identifiers
2.2.1 UNII
KR5YZ6AE4B
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Calcort

2. Dezacor

3. Emflaza

4. Zamene

2.3.2 Depositor-Supplied Synonyms

1. 14484-47-0

2. Azacort

3. Calcort

4. Oxazacort

5. Flantadin

6. Emflaza

7. Cortax

8. Deflan

9. Mdl 458

10. Mdl-458

11. L-5458

12. Kr5yz6ae4b

13. Mdl458

14. Dezacor

15. Lantadin

16. Dsstox_cid_378

17. Dsstox_rid_75552

18. Dsstox_gsid_20378

19. 2-((6ar,6bs,7s,8as,8bs,11ar,12as,12bs)-7-hydroxy-6a,8a,10-trimethyl-4-oxo-1,2,4,6a,6b,7,8,8a,11a,12,12a,12b-dodecahydro-8bh-naphtho[2',1':4,5]indeno[1,2-d]oxazol-8b-yl)-2-oxoethyl Acetate

20. Deflazacortum

21. Decortil

22. Deflanil

23. Enzocort

24. Deflazacort (calcort)

25. 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

26. Cas-14484-47-0

27. Dl-458-it

28. Unii-kr5yz6ae4b

29. Deflazacortum [inn-latin]

30. Deflazacort [usan:inn:ban]

31. Einecs 238-483-7

32. Emflaza (tn)

33. Mfcd00866106

34. Deflazacort [mi]

35. Deflazacort [inn]

36. Deflazacort (usan/inn)

37. Deflazacort [usan]

38. Schembl4018

39. Deflazacort [mart.]

40. Deflazacort [usp-rs]

41. Deflazacort [who-dd]

42. Dl-458it

43. Gtpl9477

44. Chembl1201891

45. Dtxsid9020378

46. Deflazacort, >=98% (hplc)

47. Deflazacort [orange Book]

48. Chebi:135720

49. Hms3714d15

50. Bcp08474

51. Zinc4212809

52. Tox21_112506

53. Tox21_301415

54. Bbl036672

55. S1888

56. Stl559051

57. Akos015895199

58. Tox21_112506_1

59. Ccg-220817

60. Db11921

61. Ks-1158

62. Ncgc00255189-01

63. Ncgc00263521-01

64. 11beta,21-dihydroxy-2'-methyl-5'betah-pregna-1,4-dieno(17,16-d)oxazole-3,20-dione 21-acetate

65. Hy-13609

66. Deflazacort 100 Microg/ml In Acetonitrile

67. D4523

68. D03671

69. T70289

70. Ab01274724-01

71. Ab01274724_02

72. 484d470

73. Q779118

74. Q-101371

75. 3-amino-3-(4-chloro-3-nitro-phenyl)-propionicacid

76. Deflazacort, United States Pharmacopeia (usp) Reference Standard

77. 11b,21-dihydroxy-2'-methyl-5'bh-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione 21-acetate

78. (11beta,16beta)-21-(acetyloxy)-11-hydroxy-2'-methyl-5'h-pregna-1,4-dieno(17,16-d)oxazole-3,20-dione

79. [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

80. 11.beta.,21-dihydroxy-2'-methyl-5'.beta.h-pregna-1,4-dieno(17,16-d)oxazole-3,20-dione 21-acetate

81. 2-((6ar,6bs,7s,8as,8bs,11ar,12as,12bs)-7-hydroxy-6a,8a,10-trimethyl-4-oxo-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1h-naphtho[2',1':4,5]indeno[1,2-d]oxazol-8b-yl)-2-oxoethyl Acetate

82. 5'-beta-h-pregna-1,4-dieno(17,16-d)oxazole-3,20-dione, 11-beta,21-dihydroxy-2'-methyl-, 21-acetate

83. 5'h-pregna-1,4-dieno(17,16-d)oxazole-3,20-dione, 21-(acetyloxy)-11-hydroxy-2'-methyl-, (11.beta.,16.beta.)-

84. 5'h-pregna-1,4-dieno(17,16-d)oxazole-3,20-dione, 21-(acetyloxy)-11-hydroxy-2'-methyl-, (11beta,16beta)-

2.4 Create Date
2005-08-09
3 Chemical and Physical Properties
Molecular Weight 441.5 g/mol
Molecular Formula C25H31NO6
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass441.21513771 g/mol
Monoisotopic Mass441.21513771 g/mol
Topological Polar Surface Area102 Ų
Heavy Atom Count32
Formal Charge0
Complexity996
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

Deflazacort is indicated for the treatment of Duchenne Muscular Dystrophy (DMD) in patients 2 years of age and older.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Deflazacort exerts anti-inflammatory activity in DMD, likely improving various symptoms, including muscle weakness and cardiorespiratory symptoms in addition to delaying their onset. This allows for an increased quality of life and prevents the necessity for surgical procedures, such as those for scoliosis, which is associated with DMD. Studies showed significant preservation of muscle mass in patients generally treated with 0.9 mg/kg/day of deflazacort compared to a control group. The following findings are based on clinical studies using deflazacort on a long term basis: **Effects on muscle strength** At age 16, individuals treated with long-term deflazacort had 63 4% score in muscle strength compared to a mean muscle strength score of 31 3% for control patients. Significant improvements in climbing stairs and rising from a supine position were also seen in patients taking deflazacort. **Effects on ambulation** Ambulation was significantly higher by 12 years of age and 18 years of age in patients taking deflazacort when compared with the control group. The control group showed a mean loss of ambulation of 2 years sooner than with deflazacort treatment. **Effects on cardiac function** Mean left ventricular ejection fraction (a measure of cardiac function) was higher in patients treated with deflazacort over the long term. Preservation of cardiac function was demonstrated by a mean difference in ejection fraction of about 7%, favoring study groups taking deflazacort over control groups. **Effects on spinal alignment** Children treated with deflazacort also significantly lowered the rate and severity of scoliosis and eliminated the need for scoliosis surgery after long-term treatment.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


Immunosuppressive 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DEFLAZACORT
5.3.2 FDA UNII
KR5YZ6AE4B
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

H02AB13

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


H - Systemic hormonal preparations, excl. sex hormones and insulins

H02 - Corticosteroids for systemic use

H02A - Corticosteroids for systemic use, plain

H02AB - Glucocorticoids

H02AB13 - Deflazacort


5.5 Absorption, Distribution and Excretion

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.


Route of Elimination

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.


Volume of Distribution

One study determined the volume of distribution to be 204 84 L.


Clearance

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.


5.6 Metabolism/Metabolites

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.


5.7 Biological Half-Life

The half-life of deflazacort ranges from 1.1 to 1.9 h


5.8 Mechanism of Action

Deflazacort is a corticosteroid prodrug with an active metabolite, 21-deflazacort, which binds to the glucocorticoid receptor to exert anti-inflammatory and immunosuppressive effects on the body. The exact mechanism by which deflazacort exerts its therapeutic effects in patients with DMD is unknown but likely occurs via its anti-inflammatory activities.


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Deflazacort (INH)

Date of Issue : 2022-09-30

Valid Till : 2025-07-02

Written Confirmation Number : WC-0161

Address of the Firm : 385/2, Pigdamber, Rau, Indore-453 331, MP, India

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DEFLAZACORT

NDC Package Code : 22552-0027

Start Marketing Date : 2011-08-24

End Marketing Date :