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    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
    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 Weight 508.5 g/mol
    Molecular Formula C27H34F2O7
    XLogP33.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count8
    Exact Mass508.22725974 g/mol
    Monoisotopic Mass508.22725974 g/mol
    Topological Polar Surface Area107 Ų
    Heavy Atom Count36
    Formal Charge0
    Complexity1050
    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 Information
    1 of 2  
    Drug NameDurezol
    PubMed HealthDifluprednate (Into the eye)
    Drug ClassesAnti-Inflammatory
    Drug LabelDurezol (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 IngredientDifluprednate
    Dosage FormEmulsion
    RouteOphthalmic
    Strength0.05%
    Market StatusPrescription
    CompanyAlcon Pharms

    2 of 2  
    Drug NameDurezol
    PubMed HealthDifluprednate (Into the eye)
    Drug ClassesAnti-Inflammatory
    Drug LabelDurezol (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 IngredientDifluprednate
    Dosage FormEmulsion
    RouteOphthalmic
    Strength0.05%
    Market StatusPrescription
    CompanyAlcon 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.

    API Reference Price

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    11-Jan-2021
    26-Mar-2024
    KGS
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    (USD/KGS)    		 Number of Transactions

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