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Chemistry

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Also known as: Alvesco, Omnaris, 126544-47-6, Zetonna, Rpr251526, Rpr-251526
Molecular Formula
C32H44O7
Molecular Weight
540.7  g/mol
InChI Key
LUKZNWIVRBCLON-GXOBDPJESA-N
FDA UNII
S59502J185

Ciclesonide
Ciclesonide is a nonhalogenated, synthetic, inhaled corticosteroid (ICS) with anti-inflammatory and potential antiviral activities. Upon administration by oral inhalation into the lungs, ciclesonide (CIC) is converted by local esterases to its active metabolite desisobutyryl-ciclesonide (des-CIC), which binds to intracellular glucocorticoid receptors (GRs). The ligand-bound GRs regulate gene expressions, which lead to inhibitory activities against multiple cell types, such as mast cells, eosinophils, basophils, lymphocytes, macrophages and neutrophils, and various mediators associated with inflammation, such as histamine, eicosanoids, leukotrienes and cytokines. In addition, ciclesonide may suppress the replication of human coronavirus by targeting viral nonstructural protein 15 (NSP15).
1 2D Structure

Ciclesonide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(1S,2S,4R,6R,8S,9S,11S,12S,13R)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 2-methylpropanoate
2.1.2 InChI
InChI=1S/C32H44O7/c1-18(2)28(36)37-17-25(35)32-26(38-29(39-32)19-8-6-5-7-9-19)15-23-22-11-10-20-14-21(33)12-13-30(20,3)27(22)24(34)16-31(23,32)4/h12-14,18-19,22-24,26-27,29,34H,5-11,15-17H2,1-4H3/t22-,23-,24-,26+,27+,29+,30-,31-,32+/m0/s1
2.1.3 InChI Key
LUKZNWIVRBCLON-GXOBDPJESA-N
2.1.4 Canonical SMILES
CC(C)C(=O)OCC(=O)C12C(CC3C1(CC(C4C3CCC5=CC(=O)C=CC45C)O)C)OC(O2)C6CCCCC6
2.1.5 Isomeric SMILES
CC(C)C(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@H]4[C@H]3CCC5=CC(=O)C=C[C@]45C)O)C)O[C@H](O2)C6CCCCC6
2.2 Other Identifiers
2.2.1 UNII
S59502J185
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (r)-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Cyclohexanecarboxaldehyde, 21-isobutyrate

2. Alvesco

3. Omnaris

2.3.2 Depositor-Supplied Synonyms

1. Alvesco

2. Omnaris

3. 126544-47-6

4. Zetonna

5. Rpr251526

6. Rpr-251526

7. Ciclesonide [inn]

8. 141845-82-1

9. Bi54903

10. S59502j185

11. [2-[(1s,2s,4r,6r,8s,9s,11s,12s,13r)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 2-methylpropanoate

12. [2-[(1s,2s,4r,8s,9s,11s,12s,13r)-6-cyclohexyl-11-hydroxy-9,13-dimethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl] 2-methylpropanoate

13. Osonase

14. Osonide

15. Omnair

16. Rpr 251526

17. Alvesco Hfa

18. Omnaris Hfa

19. Alvesco (tn)

20. Omnaris (tn)

21. Ciclesonide [usan:inn]

22. Btr-15k

23. Ciclesonide (jan/usan/inn)

24. Btr-15

25. Tbn-15

26. (r)-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Cyclohexanecarboxaldehyde, 21-isobutyrate

27. Unii-s59502j185

28. Ncgc00167484-01

29. (11?,16?)-16,17-[[(r)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-pregna-1,4-diene-3,20-dione

30. Alvesco 80

31. Zetonna (tn)

32. Alvesco, Ciclesonide

33. Byk-20426

34. Alvesco 160

35. By-9010

36. Ks-1165

37. Ac1miwnr

38. Ciclesonide [mi]

39. Ciclesonide [jan]

40. Ciclesonide [usan]

41. Ciclesonide [vandf]

42. Schembl3688

43. Ciclesonide [mart.]

44. Dsstox_cid_26659

45. Dsstox_rid_81802

46. Dsstox_gsid_46659

47. Ciclesonide [who-dd]

48. B-9207-015

49. Gtpl7469

50. El-87-6

51. Chembl2040682

52. Dtxsid9046659

53. Chebi:31397

54. Ciclesonide, >=98% (hplc)

55. Ciclesonide [orange Book]

56. Ciclesonide [ep Monograph]

57. Hms3714n07

58. Ex-a4195

59. Hy-b0625

60. Zinc3915154

61. Tox21_112486

62. Bdbm50247997

63. S4646

64. Akos015994702

65. Ac-1330

66. Ccg-269962

67. Db01410

68. Ncgc00167972-01

69. Pregna-1,4-diene-3,20-dione, 16,17-(((r)-cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha)-

70. Pregna-1,4-diene-3,20-dione, 16,17-((cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11beta,16alpha(r))-

71. Ciclesonide 100 Microg/ml In Acetonitrile

72. C3701

73. Cas-141845-82-1

74. C72110

75. D01703

76. 544c476

77. A899067

78. Sr-01000942227

79. Q5119448

80. Sr-01000942227-1

81. Ciclesonide, European Pharmacopoeia (ep) Reference Standard

82. (11?,16?)-16,17-[[(r)-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)pregna-1,4-diene-3,20-dione

83. 2-((6ar,6bs,7s,8as,8bs,10r,11ar,12as,12bs)-10-cyclohexyl-7-hydroxy-6a,8a-dimethyl-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][1,3]dioxol-8b-yl)-2-oxoethyl Isobutyrate

84. 2h-naphth (2',1':4,5) Indeno (1,2-d) (1,3) Dioxole, Pregna-1,4-diene-3,20-dione Deriv.

85. Pregna-1,4-diene-3,20-dione, 16,17-(((r)-cyclohexylmethylene)bis(oxy))-11-hydroxy-21-(2-methyl-1-oxopropoxy)-, (11.beta.,16.alpha.)

2.3.3 Other Synonyms

1. Desisobutyrylciclesonide

2. Desisobuytyryl Ciclesonide

3. Desisobutyryl Ciclesonide

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 540.7 g/mol
Molecular Formula C32H44O7
XLogP35.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Exact Mass540.30870374 g/mol
Monoisotopic Mass540.30870374 g/mol
Topological Polar Surface Area99.1 Ų
Heavy Atom Count39
Formal Charge0
Complexity1100
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameAlvesco
PubMed HealthCiclesonide
Drug ClassesAnti-Inflammatory, Endocrine-Metabolic Agent
Drug LabelThe active component of ALVESCO 80 mcg Inhalation Aerosol, and ALVESCO 160 mcg Inhalation Aerosol is ciclesonide, a non-halogenated glucocorticoid having the chemical name pregna-1,4-diene-3,20-dione, 16,17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydr...
Active IngredientCiclesonide
Dosage FormAerosol, metered
RouteInhalation
Strength0.08mg/inh; 0.16mg/inh
Market StatusPrescription
CompanyTakeda Gmbh

2 of 6  
Drug NameOmnaris
PubMed HealthCiclesonide
Drug ClassesAnti-Inflammatory, Endocrine-Metabolic Agent
Drug LabelThe active component of OMNARIS Nasal Spray is ciclesonide, a non-halogenated glucocorticoid having the chemical name pregna -1,4-diene-3,20-dione, 16,17-[[R-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-,(11,16)-. Ciclesoni...
Active IngredientCiclesonide
Dosage FormSpray, metered; Spray
Routenasal; Nasal
Strength50mcg; 0.05mg/inh
Market StatusPrescription
CompanyNycomed Us; Takeda Gmbh

3 of 6  
Drug NameZetonna
PubMed HealthCiclesonide
Drug ClassesAnti-Inflammatory, Endocrine-Metabolic Agent
Drug LabelThe active component of ZETONNA Nasal Aerosol is ciclesonide, a non-halogenated glucocorticoid having the chemical name pregna -1,4-diene-3,20-dione, 16,17-[[R-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-,(11,16)-. Cicleso...
Active IngredientCiclesonide
Dosage FormAerosol, metered
RouteNasal
Strength0.037mg/inh
Market StatusPrescription
CompanyTakeda Gmbh

4 of 6  
Drug NameAlvesco
PubMed HealthCiclesonide
Drug ClassesAnti-Inflammatory, Endocrine-Metabolic Agent
Drug LabelThe active component of ALVESCO 80 mcg Inhalation Aerosol, and ALVESCO 160 mcg Inhalation Aerosol is ciclesonide, a non-halogenated glucocorticoid having the chemical name pregna-1,4-diene-3,20-dione, 16,17-[[(R)-cyclohexylmethylene]bis(oxy)]-11-hydr...
Active IngredientCiclesonide
Dosage FormAerosol, metered
RouteInhalation
Strength0.08mg/inh; 0.16mg/inh
Market StatusPrescription
CompanyTakeda Gmbh

5 of 6  
Drug NameOmnaris
PubMed HealthCiclesonide
Drug ClassesAnti-Inflammatory, Endocrine-Metabolic Agent
Drug LabelThe active component of OMNARIS Nasal Spray is ciclesonide, a non-halogenated glucocorticoid having the chemical name pregna -1,4-diene-3,20-dione, 16,17-[[R-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-,(11,16)-. Ciclesoni...
Active IngredientCiclesonide
Dosage FormSpray, metered; Spray
Routenasal; Nasal
Strength50mcg; 0.05mg/inh
Market StatusPrescription
CompanyNycomed Us; Takeda Gmbh

6 of 6  
Drug NameZetonna
PubMed HealthCiclesonide
Drug ClassesAnti-Inflammatory, Endocrine-Metabolic Agent
Drug LabelThe active component of ZETONNA Nasal Aerosol is ciclesonide, a non-halogenated glucocorticoid having the chemical name pregna -1,4-diene-3,20-dione, 16,17-[[R-cyclohexylmethylene]bis(oxy)]-11-hydroxy-21-(2-methyl-1-oxopropoxy)-,(11,16)-. Cicleso...
Active IngredientCiclesonide
Dosage FormAerosol, metered
RouteNasal
Strength0.037mg/inh
Market StatusPrescription
CompanyTakeda Gmbh

4.2 Drug Indication

For the treatment of nasal symptoms associated with seasonal and perennial allergic rhinitis in adults and adolescents 12 years of age and older.


For the alleviation of clinical signs of severe equine asthma (formerly known as Recurrent Airway Obstruction (RAO), Summer Pasture Associated Recurrent Airway Obstruction (SPA-RAO)).


5 Pharmacology and Biochemistry
5.1 Pharmacology

Ciclesonide is a pro-drug that is enzymatically hydrolyzed to a pharmacologically active metabolite, C21-desisobutyryl-ciclesonide (des-ciclesonide or RM1) following intranasal application. Des-ciclesonide has anti-inflammatory activity with affinity for the glucocorticoid receptor that is 120 times higher than the parent compound. The precise mechanism through which ciclesonide affects allergic rhinitis symptoms is not known. Corticosteroids have been shown to have a wide range of effects on multiple cell types (e.g., mast cells, eosinophils, neutrophils, macrophages, and lymphocytes) and mediators (e.g., histamine, eicosanoids, leukotrienes, and cytokines) involved in allergic inflammation.


5.2 MeSH Pharmacological Classification

Anti-Allergic Agents

Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)


Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)


5.3 ATC Code

QR03BA08


R - Respiratory system

R01 - Nasal preparations

R01A - Decongestants and other nasal preparations for topical use

R01AD - Corticosteroids

R01AD13 - Ciclesonide


R - Respiratory system

R03 - Drugs for obstructive airway diseases

R03B - Other drugs for obstructive airway diseases, inhalants

R03BA - Glucocorticoids

R03BA08 - Ciclesonide


5.4 Absorption, Distribution and Excretion

Absorption

Ciclesonide and des-ciclesonide have negligible oral bioavailability (both less than 1%) due to low gastrointestinal absorption and high first-pass metabolism. The intranasal administration of ciclesonide at recommended doses results in negligible serum concentrations of ciclesonide.


Clearance

152 L/hr [Following IV administration of 800 mcg of ciclesonide]


5.5 Metabolism/Metabolites

Des-ciclesonide undergoes metabolism in the liver to additional metabolites mainly by the cytochrome P450 (CYP) 3A4 isozyme and to a lesser extent by CYP 2D6.


5.6 Mechanism of Action

Glucocorticoids such as ciclesonide can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of glucocorticoids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. Ciclesonide reduces inflammatory reaction by limiting the capillary dilatation and permeability of the vascular structures. These compounds restrict the accumulation of polymorphonuclear leukocytes and macrophages and reduce the release of vasoactive kinins. Recent research suggests that corticosteroids may inhibit the release of arachidonic acid from phospholipids, thereby reducing the formation of prostaglandins. Ciclesonide is a glucocorticoid receptor agonist. On binding, the corticoreceptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing an increase or decrease in expression of specific target genes, including suppression of IL2 (interleukin 2) expression.