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Difluprednate

Difluprednate

Synopsis, Chemistry

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Also known as: 23674-86-4, Durezol, Dfba, Myser, Epitopic, [(6s,8s,9r,10s,11s,13s,14s,17r)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate

Molecular Formula

C₂₇H₃₄F₂O₇

Molecular Weight

508.5 g/mol

InChI Key

WYQPLTPSGFELIB-JTQPXKBDSA-N

FDA UNII

S8A06QG2QE

Difluprednate is a topical corticosteroid and prednisolone acetate derivative, with anti-inflammatory activity. Upon instillation into the eye, difluprednate binds to and activates the glucocorticoid receptor (GR). The receptor-ligand complex binds to promoter regions of certain genes and initiates RNA transcription. This results in an induction of synthesis of phospholipase A2 inhibitory proteins, thereby inhibiting the synthesis of arachidonic acid and preventing the synthesis of certain inflammatory mediators, such as prostaglandins and leukotrienes. This reduces ocular inflammation and pain.

1 2D Structure

Difluprednate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate

2.1.2 InChI

InChI=1S/C27H34F2O7/c1-5-6-23(34)36-26(22(33)14-35-15(2)30)10-8-17-18-12-20(28)19-11-16(31)7-9-24(19,3)27(18,29)21(32)13-25(17,26)4/h7,9,11,17-18,20-21,32H,5-6,8,10,12-14H2,1-4H3/t17-,18-,20-,21-,24-,25-,26-,27-/m0/s1

2.1.3 InChI Key

WYQPLTPSGFELIB-JTQPXKBDSA-N

2.1.4 Canonical SMILES

CCCC(=O)OC1(CCC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C(=O)COC(=O)C

2.1.5 Isomeric SMILES

CCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2C[C@@H](C4=CC(=O)C=C[C@@]43C)F)F)O)C)C(=O)COC(=O)C

2.2 Other Identifiers

2.2.1 UNII

S8A06QG2QE

2.3 Synonyms

2.3.1 MeSH Synonyms

1. C.m.9155

2. Env905

3. Epitopic

2.3.2 Depositor-Supplied Synonyms

1. 23674-86-4

2. Durezol

3. Dfba

4. Myser

5. Epitopic

6. [(6s,8s,9r,10s,11s,13s,14s,17r)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] Butanoate

7. Difluoroprednisolone Butyrate Acetate

8. W 6309

9. Cm 9155

10. S8a06qg2qe

11. Difluprednatum

12. Mls000028663

13. Mls001148580

14. Chebi:31485

15. W-6309

16. Smr000058924

17. (6alpha,11beta)-21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dion

18. Difluprednato

19. 6alpha,9alpha-difluoroprednisolone 21-acetate 17-butyrate

20. Durezol (tn)

21. Unii-s8a06qg2qe

22. Difluprednatum [inn-latin]

23. Difluprednato [inn-spanish]

24. Difluprednate [usan:inn:jan]

25. Ncgc00168749-01

26. Einecs 245-815-4

27. Mfcd00214273

28. Opera_id_1287

29. Difluprednate [mi]

30. Difluprednate [inn]

31. Difluprednate [jan]

32. Schembl4580

33. Difluprednate [usan]

34. Dsstox_cid_26773

35. Dsstox_rid_81894

36. Dsstox_gsid_46773

37. Difluprednate [vandf]

38. Mls001333701

39. St60-1

40. Difluprednate [mart.]

41. Difluprednate [who-dd]

42. Gtpl7474

43. Chembl1201749

44. Difluprednate (jan/usan/inn)

45. Dtxsid0046773

46. 6-alpha,9-alpha-difluoroprednisolone 17-butyrate 21-acetate

47. Hms2231d18

48. Difluprednate [orange Book]

49. (6s,8s,9r,10s,11s,13s,14s,17r)-17-(2-acetoxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl Butyrate

50. Act03289

51. Zinc4212945

52. Tox21_112628

53. S4095

54. Ccg-269762

55. Db06781

56. 6alpha,9-difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate

57. 21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)pregna-1,4-diene-3,20-dione (6alpha,11beta)-

58. As-15800

59. Hy-17569

60. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)-, (6.alpha.,11.beta.)-

61. Cas-23674-86-4

62. D5579

63. D01266

64. Ab00383058_10

65. 674d864

66. A932746

67. Q736113

68. Sr-01000000265

69. Q-101389

70. Sr-01000000265-4

71. 6alpha-9-difluoroprednisolone 21-acetate 17-butyrate

72. 6 Alpha ,9 Alpha -difluoroprednisolone 21-acetate 17-butyrate

73. 6alpha,9alpha-difluoroprednisolone 21-acetate 17-butyrate, >=98%

74. (1r,2s,8s,10s,11s,14r,15s,17s)-14-[2-(acetyloxy)acetyl]-1,8-difluoro-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl Butanoate

75. 6.alpha.,9-difluoro-11.beta.,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate

76. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)-, (6alpha,11beta)-

77. Pregna-1,4-diene-3,20-dione, 6-alpha,9-difluoro-11-beta,17,21-trihydroxy-, 21-acetate, 17-butyrate

78. Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-6,9-difluoro-11-hydroxy-17-(1-oxobutoxy)-, (6a,11b)-

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₄F₂O₇
Molecular Weight	508.5 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	9
Rotatable Bond Count	8
Exact Mass	508.22725974 g/mol
Monoisotopic Mass	508.22725974 g/mol
Topological Polar Surface Area	107 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	1050
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Durezol
PubMed Health	Difluprednate (Into the eye)
Drug Classes	Anti-Inflammatory
Drug Label	Durezol (difluprednate ophthalmic emulsion) 0.05% is a sterile, topical anti-inflammatory corticosteroid for ophthalmic use. The chemical name is 6,9difluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate (CAS number 23674-...
Active Ingredient	Difluprednate
Dosage Form	Emulsion
Route	Ophthalmic
Strength	0.05%
Market Status	Prescription
Company	Alcon Pharms

2 of 2
Drug Name	Durezol
PubMed Health	Difluprednate (Into the eye)
Drug Classes	Anti-Inflammatory
Drug Label	Durezol (difluprednate ophthalmic emulsion) 0.05% is a sterile, topical anti-inflammatory corticosteroid for ophthalmic use. The chemical name is 6,9difluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate 17-butyrate (CAS number 23674-...
Active Ingredient	Difluprednate
Dosage Form	Emulsion
Route	Ophthalmic
Strength	0.05%
Market Status	Prescription
Company	Alcon Pharms

4.2 Drug Indication

For the treatment of inflammation and pain associated with ocular surgery.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Difluprednate is a corticosteroid used as an anti-inflammatory steroidal drug used primarily in ocular surgery.

5.2 MeSH Pharmacological Classification

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

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC19 - Difluprednate

5.4 Absorption, Distribution and Excretion

Absorption

Difluprednate penetrates the corneal epithelium rapidly and effectively. Low systemic absorption.

Route of Elimination

78.5% of radioactivity was excreted aftert 24 hours, and 99.5% by 7 days after a single dose of labeled difluprednate instilled in the right eyes of pigmented rabbits.

5.5 Metabolism/Metabolites

Difluprednate is rapidly deacetylated in the aqueous humor to difluoroprednisolone butyrate (DFB), the drugs active metabolite. Endogenous tissue esterases then metabolize DFB to the inert metabolite hydroxyfluoroprednisolone butyrate (HFB), which limits systemic exposure to the active compound.

5.6 Mechanism of Action

Corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins (lipocortins). It is postulated that these proteins control the biosynthesis of potent mediators of infammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2.