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    Chemistry

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    Also known as: 52-21-1, Prednisolone 21-acetate, Omnipred, Econopred, Pricortin, Cormalone
    Molecular Formula
    C23H30O6
    Molecular Weight
    402.5  g/mol
    InChI Key
    LRJOMUJRLNCICJ-JZYPGELDSA-N
    FDA UNII
    8B2807733D
    Prednisolone Acetate
    Prednisolone Acetate is the acetate salt form of prednisolone, a synthetic glucocorticoid with anti-inflammatory and immunomodulating properties. As a glucocorticoid receptor agonist, prednisolone acetate binds to specific intracellular glucocorticoid receptors, and causes the ligand-receptor complex to be translocated to the nucleus where it initiates the transcription of glucocorticoid-responsive genes such as various cytokines and lipocortins. Lipocortins inhibit phospholipase A2, thereby blocking the release of arachidonic acid from membrane phospholipids and preventing the synthesis of prostaglandins and leukotrienes, both potent mediators of inflammation. This agent also decreases the number of circulating lymphocytes, induces cell differentiation, and stimulates apoptosis in sensitive tumor cell populations.
    1 2D Structure

    Prednisolone Acetate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
    2.1.2 InChI
    InChI=1S/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h6,8,10,16-18,20,26,28H,4-5,7,9,11-12H2,1-3H3/t16-,17-,18-,20+,21-,22-,23-/m0/s1
    2.1.3 InChI Key
    LRJOMUJRLNCICJ-JZYPGELDSA-N
    2.1.4 Canonical SMILES
    CC(=O)OCC(=O)C1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)O
    2.1.5 Isomeric SMILES
    CC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    8B2807733D
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Pred Forte

    2. Prednisolone 21-acetate

    3. Scherisolone-kristall Suspension

    2.3.2 Depositor-Supplied Synonyms

    1. 52-21-1

    2. Prednisolone 21-acetate

    3. Omnipred

    4. Econopred

    5. Pricortin

    6. Cormalone

    7. Cortipred

    8. Deltilen

    9. Durapred

    10. Predicort

    11. Prednidoren

    12. Supercortyl

    13. Prenema

    14. Meticortelone Acetate

    15. Prednelan-n

    16. Delcort-e

    17. Pred Mild

    18. Pred Forte

    19. Flo-pred

    20. Prediacortine

    21. Nisolone

    22. Prednisolone-21-acetate

    23. Predalone 50

    24. Predonine Injection

    25. Nsc-10966

    26. Mls000028512

    27. Chebi:8380

    28. [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Acetate

    29. Prednisolone (21-acetate)

    30. Smr000058326

    31. Econopred Plus

    32. 8b2807733d

    33. Nsc 10966

    34. Dsstox_cid_3502

    35. Dsstox_rid_77056

    36. Dsstox_gsid_23502

    37. Prednisoloneacetate

    38. 21-acetoxy-1,4-pregnadiene-11beta,17alpha-diol-3,20-dione

    39. Pred-forte

    40. Cetapred Ointment

    41. Pred-g Liquifilm

    42. Vasocidin Ointment

    43. Cas-52-21-1

    44. Blephamide Liquifilm

    45. Einecs 200-134-1

    46. Prednisolone Acetate (omnipred)

    47. Brn 3111798

    48. Prednisolone Acetate [usp:jan]

    49. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11.beta.)-

    50. Econopred (tn)

    51. Prednisoloni Acetas

    52. Unii-8b2807733d

    53. Ncgc00094765-01

    54. Prednisolone-acetate

    55. Pred Forte (tn)

    56. Component Of Metimyd

    57. Mfcd00037710

    58. Sterane Im And Ia

    59. Blephamide S.o.p.

    60. Component Of Composone

    61. Pred Forte Tm 1%

    62. Opera_id_332

    63. Pred-g S.o.p.

    64. 11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

    65. Schembl7999

    66. Chembl1152

    67. Component Of Isopto Cetapred

    68. 4-08-00-03468 (beilstein Handbook Reference)

    69. Mls001148097

    70. Mls002207146

    71. Mls002548870

    72. Component Of Neo-delta-cortef

    73. Dtxsid3023502

    74. Hms2234f18

    75. Hms3259o07

    76. Prednisolone Acetate [jan]

    77. Prednisolone 21-acetate, >=97%

    78. Prednisone Impurity L [ep]

    79. 2-((8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl Acetate

    80. Bcp18958

    81. Hy-b1214

    82. Nsc10966

    83. Zinc3875348

    84. Prednisolone Acetate [vandf]

    85. Tox21_111328

    86. Prednisolone Acetate [mart.]

    87. Pregna-1,4-diene-3,20-dione, 11beta,17,21-trihydroxy-, 21-acetate

    88. S2570

    89. Prednisolone Acetate [usp-rs]

    90. Prednisolone Acetate [who-dd]

    91. Prednisolone Acetate [who-ip]

    92. Akos007930677

    93. Akos015960469

    94. Prednisolone 21-acetate [mi]

    95. Pregna-1,4-diene-3,20-dione, 11-beta,17,21-trihydroxy-, 21-acetate

    96. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11beta)-

    97. Tox21_111328_1

    98. Ac-2176

    99. Ccg-268673

    100. Cs-4642

    101. Db15566

    102. Nc00470

    103. Prednisolone Acetate (jp17/usp/inn)

    104. Ncgc00021925-03

    105. Ncgc00021925-05

    106. Prednisolone Acetate [green Book]

    107. 2-((1s,10s,11s,15s,17s,2r,14r)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8 .7.0.0<2,7>.0<11,15>]heptadeca-3,6-dien-14-yl)-2-oxoethyl Acetate

    108. As-11673

    109. Prednisolone Acetate [orange Book]

    110. Prednisolone Acetate [ep Monograph]

    111. Prednisolone Acetate [usp Impurity]

    112. Prednisoloni Acetas [who-ip Latin]

    113. Prednisolone Acetate [usp Monograph]

    114. Prednisolone Acetate For Peak Identification

    115. Metimyd Component Prednisolone Acetate

    116. P1283

    117. Pred-g Component Prednisolone Acetate

    118. Prednisolone Impurity C [ep Impurity]

    119. Cetapred Component Prednisolone Acetate

    120. Sulphrin Component Prednisolone Acetate

    121. Blephamide Component Prednisolone Acetate

    122. C08180

    123. D00980

    124. Poly-pred Component Prednisolone Acetate

    125. Predamide Component Prednisolone Acetate

    126. Prednisolone Acetate 100 Microg/ml In Methanol

    127. Prednisolone Acetate Component Of Pred-g

    128. Ab00443788-11

    129. Ab00443788_13

    130. Prednisolone Acetate 1000 Microg/ml In Methanol

    131. Prednisolone Acetate Component Of Cetapred

    132. Prednisolone Acetate Component Of Metimyd

    133. Prednisolone Acetate Component Of Sulphrin

    134. Predsulfair Component Prednisolone Acetate

    135. 037p710

    136. A828982

    137. Prednisolone Acetate Component Of Blephamide

    138. Prednisolone Acetate Component Of Poly-pred

    139. Prednisolone Acetate Component Of Predamide

    140. Prednisolone Acetate Component Of Predsulfair

    141. Q-201614

    142. Hydrocortisone Acetate Impurity C [ep Impurity]

    143. Isopto Cetapred Component Prednisolone Acetate

    144. Neo-delta-cortef Component Prednisolone Acetate

    145. Q27108063

    146. Blephamide S.o.p. Component Prednisolone Acetate

    147. Prednisolone Acetate Component Of Isopto Cetapred

    148. Prednisolone Acetate Component Of Neo-delta-cortef

    149. Methylprednisolone Acetate Impurity E [ep Impurity]

    150. Prednisolone 21-acetate, Vetranal(tm), Analytical Standard

    151. Prednisolone Acetate Component Of Blephamide S.o.p.

    152. 11b,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

    153. Pregna-1,20-dione, 11.beta.,17,21-trihydroxy-, 21-acetate

    154. Prednisolone Acetate, British Pharmacopoeia (bp) Reference Standard

    155. Prednisolone Acetate, European Pharmacopoeia (ep) Reference Standard

    156. (11beta)-11,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl Acetate

    157. 11.beta.,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-acetate

    158. 11.beta.,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl Acetate

    159. Prednisolone Acetate, United States Pharmacopeia (usp) Reference Standard

    160. Pregna-1,20-dione, 21-(acetyloxy)-11,17-dihydroxy-, (11.beta.)-

    161. Prednisolone Acetate For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    162. Prednisolone Acetate, Pharmaceutical Secondary Standard; Certified Reference Material

    163. [2-[(8s,9s,10r,11s,13s,14s,17r)-10,13-dimethyl-11,17-bis(oxidanyl)-3-oxidanylidene-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxidanylidene-ethyl] Ethanoate

    164. Acetic Acid [2-[(8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] Ester

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 402.5 g/mol
    Molecular Formula C23H30O6
    XLogP32.4
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count4
    Exact Mass402.20423867 g/mol
    Monoisotopic Mass402.20423867 g/mol
    Topological Polar Surface Area101 Ų
    Heavy Atom Count29
    Formal Charge0
    Complexity827
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    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 10  
    Drug NameBlephamide s.o.p.
    PubMed HealthPrednisolone
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
    Drug LabelFlo-Pred (prednisolone acetate oral suspension) contains prednisolone which is the acetate ester of the glucocorticoid prednisolone. Glucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from...
    Active Ingredientsulfacetamide sodium; Prednisolone acetate
    Dosage FormOintment
    RouteOphthalmic
    Strength0.2%; 10%
    Market StatusPrescription
    CompanyAllergan

    2 of 10  
    Drug NameFlo-pred
    PubMed HealthPrednisolone
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
    Drug LabelOMNIPRED (prednisolone acetate ophthalmic suspension) is an adrenocortical steroid product prepared as sterile ophthalmic suspension. The active ingredient is represented by the chemical structure:Established name: Prednisolone AcetateChemical name...
    Active IngredientPrednisolone acetate
    Dosage FormSuspension
    RouteOral
    Strengtheq 15mg base/5ml
    Market StatusPrescription
    CompanyTaro

    3 of 10  
    Drug NameOmnipred
    PubMed HealthPrednisolone (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelPRED FORTE (prednisolone acetate ophthalmic suspension, USP) 1% is a topical anti-inflammatory agent for ophthalmic use....
    Active IngredientPrednisolone acetate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength1%
    Market StatusPrescription
    CompanyAlcon

    4 of 10  
    Drug NamePred forte
    Drug LabelPRED MILD (prednisolone acetate ophthalmic suspension, USP) 0.12% is a topical anti-inflammatory agent for ophthalmic use. Structural Formula:...
    Active IngredientPrednisolone acetate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength1%
    Market StatusPrescription
    CompanyAllergan

    5 of 10  
    Drug NamePred mild
    Active IngredientPrednisolone acetate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength0.12%
    Market StatusPrescription
    CompanyAllergan

    6 of 10  
    Drug NameBlephamide s.o.p.
    PubMed HealthPrednisolone
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
    Drug LabelFlo-Pred (prednisolone acetate oral suspension) contains prednisolone which is the acetate ester of the glucocorticoid prednisolone. Glucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from...
    Active Ingredientsulfacetamide sodium; Prednisolone acetate
    Dosage FormOintment
    RouteOphthalmic
    Strength0.2%; 10%
    Market StatusPrescription
    CompanyAllergan

    7 of 10  
    Drug NameFlo-pred
    PubMed HealthPrednisolone
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppressant, Ophthalmologic Agent
    Drug LabelOMNIPRED (prednisolone acetate ophthalmic suspension) is an adrenocortical steroid product prepared as sterile ophthalmic suspension. The active ingredient is represented by the chemical structure:Established name: Prednisolone AcetateChemical name...
    Active IngredientPrednisolone acetate
    Dosage FormSuspension
    RouteOral
    Strengtheq 15mg base/5ml
    Market StatusPrescription
    CompanyTaro

    8 of 10  
    Drug NameOmnipred
    PubMed HealthPrednisolone (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelPRED FORTE (prednisolone acetate ophthalmic suspension, USP) 1% is a topical anti-inflammatory agent for ophthalmic use....
    Active IngredientPrednisolone acetate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength1%
    Market StatusPrescription
    CompanyAlcon

    9 of 10  
    Drug NamePred forte
    Drug LabelPRED MILD (prednisolone acetate ophthalmic suspension, USP) 0.12% is a topical anti-inflammatory agent for ophthalmic use. Structural Formula:...
    Active IngredientPrednisolone acetate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength1%
    Market StatusPrescription
    CompanyAllergan

    10 of 10  
    Drug NamePred mild
    Active IngredientPrednisolone acetate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength0.12%
    Market StatusPrescription
    CompanyAllergan

    4.2 Drug Indication

    Prednisolone acetate is indicated as an anti-inflammatory or immunosuppressive agent for allergic, dermatologic, gastrointestinal, hematologic, ophthalmologic, nervous system, renal, respiratory, rheumatologic, or infectious conditions. Prednisolone acetate is also indicated in organ transplant patients, as well as endocrine or neoplastic conditions.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Prednisolone acetate has a short duration of action as the half life is 2-3 hours. Corticosteroids have a wide therapeutic window as patients make require doses that are multiples of what the body naturally produces. Patients taking corticosteroids should be counselled regarding the risk of hypothalamic-pituitary-adrenal axis suppression and increased susceptibility to infections.

    5.2 MeSH Pharmacological Classification

    Anti-Inflammatory Agents

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

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.4 Absorption, Distribution and Excretion

    Absorption

    Prednisolone acetate oral suspension given at a dose equivalent to 15mg prednisolone has a Cmax of 321.1ng/hr, a Tmaxof 1-2 hours, and an AUC of 1999.4ng\*hr/mL. The absorption pharmacokinetics of prednisolone acetate are not significantly different from a comparable dose of prednisolone.

    Route of Elimination

    Prednisolone acetate is predominantly excreted in the urine.

    Volume of Distribution

    The volume of distribution of the active metabolite, prednisolone, is 0.22/0.7L/kg.

    Clearance

    Data regarding the clearance of prednisolone acetate is not readily available.

    5.5 Metabolism/Metabolites

    Prednisolone acetate undergoes ester hydrolysis to [prednisolone]. After this step, the drug undergoes the normal metabolism of prednisolone. Prednisolone can be reversibly metabolized to [prednisone] which is then metabolized to 17,21-dihydroxy-pregnan-1,4,6-trien-3,11,30-trione (M-XVII), 20-dihydro-prednisone (M-V), 6hydroxy-prednisone (M-XII), 6-hydroxy-prednisone (M-XIII), or 20-dihydro-prednisone (M-IV). 20-dihydro-prednisone is metabolized to 17,20,21-trihydroxy-5-pregn-1-en-3,11-dione(M-XVIII). Prednisolone is metabolized to 6-prednisolone (M-XI), 20-dihydro-prednisolone (M-III), 20-dihydro-prednisolone (M-II), 6hydroxy-prednisolone (M-VII), or 6hydroxy-prednisolone(M-VI). 6hydroxy-prednisolone is metabolized to 6,11,17,20,21-pentahydroxypregnan-1,4-diene-3-one (M-X). 6hydroxy-prednisolone is metabolized to 6,11,17,20,21-pentahydroxypregnan-1,4-diene-3-one (M-VIII), 6,11,17,20,21-pentahydroxypregnan-1,4-diene-3-one (M-IX), and 6,11,17,21-tetrahydroxy-5-pregn-1-en-3,20-dione (M-XIV). MVIII is metabolized to 6,11,17,20,21-pentahydroxy-5-pregn-1-en-3-one (M-XV) and then to MXIV, while MIX is metabolized to 6,11,17,20,21-pentahydroxy-5-pregn-1-en-3-one (M-XVI) and then to MXIV. These metabolites and their glucuronide conjugates are excreted predominantly in the urine.

    5.6 Biological Half-Life

    Oral prednisolone acetate has a plasma half life of 2-3 hours.

    5.7 Mechanism of Action

    The short term effects of corticosteroids are decreased vasodilation and permeability of capillaries, as well as decreased leukocyte migration to sites of inflammation. Corticosteroids binding to the glucocorticoid receptor mediates changes in gene expression that lead to multiple downstream effects over hours to days. Glucocorticoids inhibit neutrophil apoptosis and demargination; they inhibit phospholipase A2, which decreases the formation of arachidonic acid derivatives; they inhibit NF-Kappa B and other inflammatory transcription factors; they promote anti-inflammatory genes like interleukin-10. Lower doses of corticosteroids provide an anti-inflammatory effect, while higher doses are immunosuppressive. High doses of glucocorticoids for an extended period bind to the mineralocorticoid receptor, raising sodium levels and decreasing potassium levels.

    API Reference Price

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    20-Jan-2021
    20-Nov-2024
    KGS
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    Average Price (USD/KGS)

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - SUSPENSION;OPHTHALMIC - 0.2%;10%

    USFDA APPLICATION NUMBER - 12813

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    DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 1%

    USFDA APPLICATION NUMBER - 17011

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    DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 0.12%

    USFDA APPLICATION NUMBER - 17100

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    DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - 1%

    USFDA APPLICATION NUMBER - 17469

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    DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - EQ 0.3...DOSAGE - SUSPENSION/DROPS;OPHTHALMIC - EQ 0.3% BASE;1%

    USFDA APPLICATION NUMBER - 50586

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    DOSAGE - OINTMENT;OPHTHALMIC - EQ 0.3% BASE;0...DOSAGE - OINTMENT;OPHTHALMIC - EQ 0.3% BASE;0.6%

    USFDA APPLICATION NUMBER - 50612

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