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    Chemistry

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    Also known as: 50-24-8, Metacortandralone, Hydroretrocortine, Predonine, Delta-cortef, Deltacortril
    Molecular Formula
    C21H28O5
    Molecular Weight
    360.4  g/mol
    InChI Key
    OIGNJSKKLXVSLS-VWUMJDOOSA-N
    FDA UNII
    9PHQ9Y1OLM
    Prednisolone
    A glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated, except adrenal deficiency states.
    Prednisolone is a Corticosteroid. The mechanism of action of prednisolone is as a Corticosteroid Hormone Receptor Agonist.
    1 2D Structure

    Prednisolone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
    2.1.2 InChI
    InChI=1S/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-16,18,22,24,26H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
    2.1.3 InChI Key
    OIGNJSKKLXVSLS-VWUMJDOOSA-N
    2.1.4 Canonical SMILES
    CC12CC(C3C(C1CCC2(C(=O)CO)O)CCC4=CC(=O)C=CC34C)O
    2.1.5 Isomeric SMILES
    C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1CC[C@@]2(C(=O)CO)O)CCC4=CC(=O)C=C[C@]34C)O
    2.2 Other Identifiers
    2.2.1 UNII
    9PHQ9Y1OLM
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Di Adreson F

    2. Di-adreson-f

    3. Diadresonf

    4. Predate

    5. Predonine

    2.3.2 Depositor-Supplied Synonyms

    1. 50-24-8

    2. Metacortandralone

    3. Hydroretrocortine

    4. Predonine

    5. Delta-cortef

    6. Deltacortril

    7. Meticortelone

    8. Deltahydrocortisone

    9. Codelcortone

    10. Cortalone

    11. Prenolone

    12. Sterane

    13. Hydroretrocortin

    14. Meti-derm

    15. Prdl

    16. Deltacortenol

    17. Hydrodeltalone

    18. Hydrodeltisone

    19. Cotogesic

    20. Decaprednil

    21. Delcortol

    22. Deltisilone

    23. Dicortol

    24. Donisolone

    25. Dydeltrone

    26. Erbacort

    27. Erbasona

    28. Estilsona

    29. Fernisolone

    30. Hydeltra

    31. Hydeltrone

    32. Lentosone

    33. Paracortol

    34. Paracotol

    35. Precortancyl

    36. Precortilon

    37. Precortisyl

    38. Prednelan

    39. Prednicen

    40. Predniliderm

    41. Predonin

    42. Rolisone

    43. Scherisolon

    44. Sterolone

    45. Cordrol

    46. Prednis

    47. Prelone

    48. Steran

    49. Ulacort

    50. Fernisolone P

    51. Hostacortin H

    52. Ultracorten H

    53. Ultracortene-h

    54. Delta-stab

    55. Predne-dome

    56. Decortin H

    57. Co-hydeltra

    58. Eazolin D

    59. Di-adreson F

    60. Delta F

    61. Derpo Pd

    62. 1-dehydrohydrocortisone

    63. Solone

    64. Delta(1)-hydrocortisone

    65. Fernisolone-p

    66. Delta(1)-dehydrocortisol

    67. Delta-ef-cortelan

    68. Dexa-cortidelt Hostacortin H

    69. 1,2-dehydrohydrocortisone

    70. Panafcortelone

    71. Prednisolona

    72. Prednisolonum

    73. Prednisolonum [inn-latin]

    74. Prednisolona [inn-spanish]

    75. 1,4-pregnadiene-11beta,17alpha,21-triol-3,20-dione

    76. (11beta)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione

    77. Ultracortene-hydrogen

    78. Delta(1)-dehydrohydrocortisone

    79. 1,4-pregnadiene-3,20-dione-11beta,17alpha,21-triol

    80. 3,20-dioxo-11beta,17alpha,21-trihydroxy-1,4-pregnadiene

    81. 11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

    82. K 1557

    83. .delta.1-cortisol

    84. Nsc-9120

    85. Nsc-9900

    86. .delta.1-hydrocortisone

    87. 9phq9y1olm

    88. (8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one

    89. .delta.1-dehydrocortisol

    90. Chembl131

    91. Chebi:8378

    92. .delta.1-dehydrohydrocortisone

    93. 11beta,17alpha,21-trihydroxypregna-1,4-diene-3,20-dione

    94. Predniretard

    95. Poly-pred

    96. .delta.-cortef

    97. Neo-delta-cortef

    98. .delta.-stab

    99. Component Of Ataraxoid

    100. Cotolone

    101. Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11b)-

    102. Dsstox_cid_1184

    103. Component Of K-predne-dome

    104. Dsstox_rid_75996

    105. Dsstox_gsid_21184

    106. (1s,2r,10s,11s,14r,15s,17s)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

    107. (8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3h-cyclopenta[a]phenanthren-3-one

    108. Delta(1)-cortisol

    109. Deltasolone

    110. Klismacort

    111. Supercortisol

    112. Delta(sup 1)-cortisol

    113. Bubbli-pred

    114. Delta(sup 1)-hydrocortisone

    115. Delta(sup 1)-dehydrocortisol

    116. Smr000718761

    117. Ccris 980

    118. Prednisolone [inn:ban:jan]

    119. Hsdb 3385

    120. Delta(sup 1)-dehydrohydrocortisone

    121. Mls002638110

    122. Nsc 9120

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

    124. Einecs 200-021-7

    125. Unii-9phq9y1olm

    126. Mfcd00003649

    127. Predisolone Sodium Phosphate

    128. Brn 1354103

    129. Prednisolon

    130. Preflam

    131. Pregna-1,20-dione, 11,17,21-trihydroxy-, (11.beta.)-

    132. Cas-50-24-8

    133. Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11beta)-

    134. Ncgc00094764-01

    135. Prednisolone Powder

    136. Delta-hydrocortisone

    137. Prestwick_404

    138. Delta-dehydrocortisol

    139. Delta.1-cortisol

    140. Aprednislon

    141. Equisolon

    142. Vetsolone

    143. Delta-cortef (tn)

    144. 11-beta,17,21-trihydroxypregna-1,4-diene-3,20-dione

    145. T-pred (salt/mix)

    146. 1,4-pregnadien-11-beta,17-alpha,21-triol-3,20-dione

    147. 1,4-pregnadiene-11-beta,17-alpha,21-triol-3,20-dione

    148. 1,4-pregnadiene-3,20-dione-11-beta,17-alpha,21-triol

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

    150. Prednisolone, >=99%

    151. Prestwick0_000274

    152. Prestwick1_000274

    153. Prestwick2_000274

    154. Prestwick3_000274

    155. Delta-dehydrohydrocortisone

    156. Prednisolone [ep]

    157. Prednisolone [mi]

    158. (+)-prednisolone

    159. Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11.beta.)-

    160. Prednisolone [inn]

    161. Prednisolone [jan]

    162. Ec 200-021-7

    163. Prednisolone [hsdb]

    164. Schembl3233

    165. K-predne-dome (salt/mix)

    166. Prednisolone [vandf]

    167. Prednisolone Anhydrous

    168. .delta.(sup 1)-cortisol

    169. Bspbio_000148

    170. Prednisolone [mart.]

    171. (11alpha)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione

    172. 4-08-00-03467 (beilstein Handbook Reference)

    173. Mls001304083

    174. Mls002154250

    175. Mls002207037

    176. Mls002548883

    177. Prednisolone [usp-rs]

    178. Prednisolone [who-dd]

    179. Prednisolone [who-ip]

    180. Spbio_002367

    181. Bpbio1_000164

    182. Gtpl2866

    183. Dtxsid9021184

    184. .delta.(sup 1)-hydrocortisone

    185. Bdbm19190

    186. Prednisolone (jp17/usp/inn)

    187. Nsc9120

    188. Nsc9900

    189. Prednisolone [green Book]

    190. .delta.(sup 1)-dehydrocortisol

    191. Hms1568h10

    192. Hms2090j05

    193. Hms2095h10

    194. Hms2230p10

    195. Hms3259e09

    196. Hms3712h10

    197. Prednisolone [orange Book]

    198. Prednisolone [ep Monograph]

    199. Prednisone Impurity B [ep]

    200. Bcp09053

    201. Zinc3833821

    202. Prednisolone [usp Monograph]

    203. Tox21_111327

    204. Tox21_201673

    205. Tox21_302987

    206. Lmst02030179

    207. Prednisolonum [who-ip Latin]

    208. S1737

    209. .delta.(sup 1)-dehydrohydrocortisone

    210. Akos015894935

    211. Tox21_111327_1

    212. Ac-1773

    213. Ccg-220274

    214. Db00860

    215. Nc00473

    216. Ncgc00179649-01

    217. Ncgc00179649-02

    218. Ncgc00179649-03

    219. Ncgc00179649-04

    220. Ncgc00179649-06

    221. Ncgc00256577-01

    222. Ncgc00259222-01

    223. As-13665

    224. Hy-17463

    225. Prednisolone 1000 Microg/ml In Methanol

    226. Prednisolone (ema Epar: Veterinary)

    227. Prednisolone 100 Microg/ml In Acetonitrile

    228. P0637

    229. En300-53017

    230. Prednicarbate Impurity A [ep Impurity]

    231. C07369

    232. D00472

    233. D91990

    234. Hydrocortisone Impurity A [ep Impurity]

    235. Prednisolone, Vetranal(tm), Analytical Standard

    236. 003p649

    237. A929791

    238. Chloroptic-p S.o.p. Component Prednisolone

    239. Methylprednisolone Impurity K [ep Impurity]

    240. Sr-01000837502

    241. Q-201616

    242. Sr-01000837502-2

    243. 11b,17,21-trihydroxypregna-1,4-diene-3,20-dione

    244. Brd-k98039984-001-03-0

    245. Brd-k98039984-001-06-3

    246. Prednisolone Acetate Impurity B [ep Impurity]

    247. Prednisolone Component Of Chloroptic-p S.o.p.

    248. Q11426176

    249. 11beta,17,21-trihydroxy-1,4-pregnadiene-3,20-dione

    250. Delta-1-cortisol; Prednicarbate Ep Imp A; Supercortisol

    251. Prednisolone, British Pharmacopoeia (bp) Assay Standard

    252. Z1245633279

    253. 11-.beta.,17,21-trihydroxypregna-1,4-diene-3,20-dione

    254. 1,4-pregnadien-11-.beta.,17-.alpha.,21-triol-3,20-dione

    255. 1,4-pregnadiene-11-.beta.,17-.alpha.,21-triol-3,20-dione

    256. 1,4-pregnadiene-3,20-dione-11-.beta.,17-.alpha.,21-triol

    257. Prednisolone, European Pharmacopoeia (ep) Reference Standard

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

    259. 11,17,21-trihydroxypregna-1,4-diene-3,20-dione, (11.beta.)-

    260. 11-.beta.,17-.alpha.,21-trihydroxy-1,4-pregnadiene-3,20-dione

    261. 11-.beta.,17-.alpha.,21-trihydroxypregna-1,4-diene-3,20-dione

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

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

    264. 11.beta.,17.alpha.,21-trihydroxypregna-1,4-diene-3,20-dione

    265. Prednisolone, United States Pharmacopeia (usp) Reference Standard

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

    267. Prednisolone For System Suitability, European Pharmacopoeia (ep) Reference Standard

    268. Prednisolone, Pharmaceutical Secondary Standard; Certified Reference Material

    269. Pregna-1,4-diene-3,20-dione, 11,17,21-trihydroxy-, (11.beta)-

    270. (1s,2r,10s,11s,14r,15s,17s)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0;{2,7}.0;{11,15}]heptadeca-3,6-dien-5-one

    271. (8s,9s,10r,11s,13s,14s,17r)-11,17-dihydroxy-8,10,13-trimethyl-3-oxo-6,7,9,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic Acid;prednisolone

    272. 8056-11-9

    273. Prednisolone Solution, 100 Mug/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

    274. Tua

    2.3.3 Other Synonyms

    1. Hydeltra-t.b.a.

    2. Prednisolone Tebutate

    3. Prednisolone Trimethylacetate

    4. Prednisolone Pivalate

    5. Sintisone

    6. Prednisolone Steaglate

    7. Prednisolone Succinate

    8. Prednisolone Sodium Succinate

    9. Prednisolone Hemisuccinate

    10. Prednisolone Hydrogen Succinate

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 360.4 g/mol
    Molecular Formula C21H28O5
    XLogP31.6
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count2
    Exact Mass360.19367399 g/mol
    Monoisotopic Mass360.19367399 g/mol
    Topological Polar Surface Area94.8 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity724
    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 12  
    Drug NameBlephamide
    PubMed HealthSulfacetamide/Prednisolone (Into the eye)
    Drug ClassesSulfonamide/Corticosteroid Combination
    Active Ingredientsulfacetamide sodium; Prednisolone acetate
    Dosage FormSuspension
    RouteOphthalmic
    Strength0.2%; 10%
    Market StatusPrescription
    CompanyAllergan

    2 of 12  
    Drug NameOrapred
    PubMed HealthPrednisolone (By mouth)
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppreant
    Active IngredientPrednisolone sodium phosphate
    Dosage FormSolution
    RouteOral
    Strengtheq 15mg base/5ml
    Market StatusPrescription
    CompanyConcordia Pharms

    3 of 12  
    Drug NamePediapred
    PubMed HealthPrednisolone
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
    Active IngredientPrednisolone sodium phosphate
    Dosage FormSolution
    RouteOral
    Strengtheq 5mg base/5ml
    Market StatusPrescription
    CompanySeton Pharm

    4 of 12  
    Drug NamePred-g
    Active Ingredientprednisolone acetate; Gentamicin sulfate
    Dosage FormOintment; Suspension/drops
    RouteOphthalmic
    Strength1%; 0.6%; eq 0.3% base
    Market StatusPrescription
    CompanyAllergan

    5 of 12  
    Drug NamePrednisolone
    Drug LabelDESCRIPTIONPrednisolone Oral Solution contains prednisolone which is a glucocorticoid. Glucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from the gastrointestinal tract. Prednisolone is a...
    Active IngredientPrednisolone
    Dosage FormTablet; Syrup
    RouteOral
    Strength15mg/5ml; 5mg
    Market StatusPrescription
    CompanyWockhardt; Alpharma; Pharm Aoc; Watson Labs; Hi Tech Pharma; Vintage

    6 of 12  
    Drug NamePrelone
    Active IngredientPrednisolone
    Dosage FormSyrup
    RouteOral
    Strength15mg/5ml
    Market StatusPrescription
    CompanyTeva

    7 of 12  
    Drug NameBlephamide
    PubMed HealthSulfacetamide/Prednisolone (Into the eye)
    Drug ClassesSulfonamide/Corticosteroid Combination
    Active Ingredientsulfacetamide sodium; Prednisolone acetate
    Dosage FormSuspension
    RouteOphthalmic
    Strength0.2%; 10%
    Market StatusPrescription
    CompanyAllergan

    8 of 12  
    Drug NameOrapred
    PubMed HealthPrednisolone (By mouth)
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppreant
    Active IngredientPrednisolone sodium phosphate
    Dosage FormSolution
    RouteOral
    Strengtheq 15mg base/5ml
    Market StatusPrescription
    CompanyConcordia Pharms

    9 of 12  
    Drug NamePediapred
    PubMed HealthPrednisolone
    Drug ClassesEndocrine-Metabolic Agent, Immune Suppreant, Ophthalmologic Agent
    Active IngredientPrednisolone sodium phosphate
    Dosage FormSolution
    RouteOral
    Strengtheq 5mg base/5ml
    Market StatusPrescription
    CompanySeton Pharm

    10 of 12  
    Drug NamePred-g
    Active Ingredientprednisolone acetate; Gentamicin sulfate
    Dosage FormOintment; Suspension/drops
    RouteOphthalmic
    Strength1%; 0.6%; eq 0.3% base
    Market StatusPrescription
    CompanyAllergan

    11 of 12  
    Drug NamePrednisolone
    Drug LabelDESCRIPTIONPrednisolone Oral Solution contains prednisolone which is a glucocorticoid. Glucocorticoids are adrenocortical steroids, both naturally occurring and synthetic, which are readily absorbed from the gastrointestinal tract. Prednisolone is a...
    Active IngredientPrednisolone
    Dosage FormTablet; Syrup
    RouteOral
    Strength15mg/5ml; 5mg
    Market StatusPrescription
    CompanyWockhardt; Alpharma; Pharm Aoc; Watson Labs; Hi Tech Pharma; Vintage

    12 of 12  
    Drug NamePrelone
    Active IngredientPrednisolone
    Dosage FormSyrup
    RouteOral
    Strength15mg/5ml
    Market StatusPrescription
    CompanyTeva

    4.2 Therapeutic Uses

    Anti-Inflammatory Agents, Steroidal; Antineoplastic Agents, Hormonal; Glucocorticoids, Synthetic

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    Ophthalmic corticosteroids are indicated in the treatment of corticosteroid-responsive allergic and inflammatory conditions of the palpebral and bulbar conjunctiva, cornea, and anterior segment of the globe. /Corticosteroids (Ophthalmic); Included in US product labeling/

    Thomson/Micromedex. Drug Information for the Health Care Professional. Volume 1, Greenwood Village, CO. 2007., p. 906

    VET: Hormonal therapy for neoplasia commonly involves the use of glucocorticoids. Direct antitumor effects are related to their lympholytic properties; glucocorticoids can inhibit mitosis, RNA synthesis, and protein synthesis in sensitive lymphocytes. Glucocorticoids are considered cell-cycle nonspecific and are often used in chemotherapeutic protocols after induction by another agent. Prednisolone /is/ commonly used to treat lymphoreticular neoplasms in combination with other drugs. Because /it/ readily enters the CSF, ... prednisolone /is/ especially useful in treatment of leukemias and lymphomas of the CNS.

    Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2150

    Indicated in a wide range of endocrine, rheumatic, allergic, dermatologic, respiratory, hematologic, neoplastic, and other disorders.

    Hussar, D.A. (ed.). Modell's Drugs in Current Use and New Drugs. 38th ed. New York, NY: Springer Publishing Co., 1992., p. 135

    For more Therapeutic Uses (Complete) data for PREDNISOLONE (28 total), please visit the HSDB record page.

    4.3 Drug Warning

    VET: IT OFTEN MAY BE CONTRAINDICATED IN CONGESTIVE HEART FAILURE, DIABETES OR OSTEOPOROSIS. EXCEPT FOR EMERGENCY LIFE SAVING USE, IT SHOULD BE OMITTED IN TUBERCULOSIS, CHRONIC NEPHRITIS, CUSHINGOID SYNDROMES, & PEPTIC ULCER CASES.

    Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 479

    Side effects and compliance were examined in 63 pediatric patients (ages 10 mo-14 yr) with acute asthma who received an oral dose of 1-2 mg/kg prednisolone (Solone; Panafcortelone) as a whole or crushed tablet or in liquid form for 7 days. Up to 44% of patients either refused to take or vomited the drug on the first day. Improved acceptability of prednisolone occurred with time, but prescribing practices indicated short-term treatment of 1 to 4 days was common. Abdominal pain and mood changes occurred in 19% and 80% of patients, respectively, at some stage of the study period. It was concluded that oral prednisolone is poorly tolerated in pediatric patients and its use may lead to suboptimal therapy.

    Dawson KP et al; Aust J Hosp Pharm 22 (Aug): 278-82 (1992)

    Glucocorticoid use in children is not only associated with the side effects which are seen in adults, but also with severe adverse effects on statural growth. As little as 2.5-5.0 mg prednisolone/day can cause a retardation in statural growth. A direct relationship exists between the dose of glucocorticoid used and statural growth. The use of knemometry, a sensitive technique for measuring the growth of long bones in children has increased the accuracy of growth rate measurements. Many factors, such as disease process, sex, daily vs alternate day therapy, ethnic variations or whether the patient has been immobilized must be considered when evaluating the effects on stature of a particular glucocorticoid.

    PMID:8495277 Avioli LV; Br J Rheumatol 32 (Suppl 2): 27-30 (1993)

    RESULTS FROM CONTROLLED TRIAL, INDICATE THAT PREDNISOLONE TREATMENT IS NOT BENEFICIAL & CAN BE DETRIMENTAL IN ACUTE NEUROPATHY OF UNDETERMINED ETIOLOGY.

    PMID:80682 HUGHES RAC ET AL; LANCET 2 (OCT 7): 750 (1978)

    For more Drug Warnings (Complete) data for PREDNISOLONE (48 total), please visit the HSDB record page.

    4.4 Drug Indication

    Prednisolone is indicated to treat endocrine, rheumatic, and hematologic disorders; collagen, dermatologic, ophthalmic, respiratory, and gastrointestinal diseases; allergic and edematous states; and other conditions like tuberculous meningitis.

    FDA Label

    Alleviation of inflammatory and clinical parameters associated with recurrent airway obstruction (RAO) in horses, in combination with environmental control.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Corticosteroids bind to the glucocorticoid receptor, inhibiting pro-inflammatory signals, and promoting anti-inflammatory signals. Prednisolone has a short duration of action as the half life is 2.1-3.5 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.)

    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.)

    Antineoplastic Agents, Hormonal

    Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079) (See all compounds classified as Antineoplastic Agents, Hormonal.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    PREDNISOLONE
    5.3.2 FDA UNII
    9PHQ9Y1OLM
    5.3.3 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.4 ATC Code

    QH02AB06

    S01BA04

    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

    A - Alimentary tract and metabolism

    A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

    A07E - Intestinal antiinflammatory agents

    A07EA - Corticosteroids acting locally

    A07EA01 - Prednisolone

    C - Cardiovascular system

    C05 - Vasoprotectives

    C05A - Agents for treatment of hemorrhoids and anal fissures for topical use

    C05AA - Corticosteroids

    C05AA04 - Prednisolone

    D - Dermatologicals

    D07 - Corticosteroids, dermatological preparations

    D07A - Corticosteroids, plain

    D07AA - Corticosteroids, weak (group i)

    D07AA03 - Prednisolone

    D - Dermatologicals

    D07 - Corticosteroids, dermatological preparations

    D07X - Corticosteroids, other combinations

    D07XA - Corticosteroids, weak, other combinations

    D07XA02 - Prednisolone

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

    H02 - Corticosteroids for systemic use

    H02A - Corticosteroids for systemic use, plain

    H02AB - Glucocorticoids

    H02AB06 - Prednisolone

    R - Respiratory system

    R01 - Nasal preparations

    R01A - Decongestants and other nasal preparations for topical use

    R01AD - Corticosteroids

    R01AD02 - Prednisolone

    S - Sensory organs

    S01 - Ophthalmologicals

    S01B - Antiinflammatory agents

    S01BA - Corticosteroids, plain

    S01BA04 - Prednisolone

    S - Sensory organs

    S01 - Ophthalmologicals

    S01C - Antiinflammatory agents and antiinfectives in combination

    S01CB - Corticosteroids/antiinfectives/mydriatics in combination

    S01CB02 - Prednisolone

    S - Sensory organs

    S02 - Otologicals

    S02B - Corticosteroids

    S02BA - Corticosteroids

    S02BA03 - Prednisolone

    S - Sensory organs

    S03 - Ophthalmological and otological preparations

    S03B - Corticosteroids

    S03BA - Corticosteroids

    S03BA02 - Prednisolone

    5.5 Absorption, Distribution and Excretion

    Absorption

    Oral prednisolone reaches a Cmax of 113-1343ng/mL with a Tmax of 1.0-2.6 hours. Oral prednisolone is approximately 70% bioavailable.

    Route of Elimination

    Prednisolone is over 98% eliminated in urine.

    Volume of Distribution

    A 0.15mg/kg dose of prednisolone has a volume of distribution of 29.3L, while a 0.30mg/kg dose has a volume of distribution of 44.2L.

    Clearance

    A 0.15mg/kg dose of prednisolone has a clearance of 0.09L/kg/h, while a 0.30mg/kg dose has a clearance of 0.12L/kg/h.

    A randomized crossover study was conducted to compare the pharmacokinetics and pharmacodynamics of 30 mg prednisolone in a plain oral tablet (Precortisyl) with those of an enteric coated tablet (Deltacortril) in 8 patients (ages 63-81 yr) with chronic obstructive pulmonary disease and in 8 healthy males (ages 22-44 yr). Although drug absorption was considerably slower from the enteric coated tablet, peak plasma levels and total area under the concn-time curve were equivalent for the formulations. Adrenal suppression was significantly less in volunteers after enteric coated than after plain tablets. This difference was not significant in patients. Plasma cortisol levels declined more slowly after enteric coated tablets in both groups. Blood glucose levels increased over 8 hr in both groups. It was concluded that in patients with chronic obstructive pulmonary disease, peak plasma levels and total area under the concn-time curve of plain and enteric coated prednisolone tablets are equivalent; enteric coated tablets result in a lag in the decline of plasma cortisol and, in volunteers, a less marked suppression of cortisol.

    PMID:1524961 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1381435 Adair CG et al; Br J Clin Pharmacol 33 (5): 495-9 (1992)

    The transfer of prednisolone to breast milk was studied in 3 nursing women (ages 28-37 yr) who received an intravenous injection of 50 mg prednisolone sodium phosphate (Hydeltrasol). Concn of prednisolone in milk declined more rapidly than in serum, but were similar to expected unbound serum levels. Milk levels ranged from about 15% to 40% of serum levels. The exchange between unbound drug in serum and breast milk appeared to be relatively rapid and bidirectional. An average of 0.025% (0.01-0.49%) of the prednisolone dose was recovered in milk. It was concluded that the transfer of prednisolone to breast milk does not appear to pose a clinically significant risk.

    PMID:8453851 Greenberger PA et al; Clin Pharmacol Ther 53 (3): 324-8 (1993)

    The pharmacokinetics of prednisolone after oral and intravenous administration of 10 and 20 mg have been studied. Serum protein binding of prednisolone was also measured after the iv injections. The bioavailability after oral administration was 84.5% after 10 mg and 77.6% after 20 mg (p>0.05). Dose dependent pharmacokinetics were found, the VDss and Clt being significantly larger (p<0.01) after 20 mg iv than after 10 mg iv. The protein binding of prednisolone in all subjects was non-linear, and is the most likely cause of the dose dependent pharmacokinetics, as there was no dose dependent variation in elimination half-time.

    PMID:6861855 Bergrem H et al; Eur J Clin Pharmacol 24 (3): 415-9 (1983)

    Doses of 16, 32, 48 and 64 mg prednisolone were administered intravenously to normal volunteers who also received 100 prednisolone orally. Plasma prednisolone concentrations were estimated by quantitative thin layer chromatography. The bioavailability fraction was 1.063 +/- 0.154 (s.d.) indicating complete availability of prednisolone following oral administration. The mean T 1/2 over all doses were 4.11 +/- 0.97 (s.d.) hr and there was no evidence of a dose-related change in its value. The mean systemic clearance over all doses was 0.104 +/- 0.034 (s.d) L/hr/kg. There was no evidence of a dose-related change in clearance or in the apparent volume of distribution (overall mean 0.588 +/- 0.152 L/kg). The area under the plasma concentration-time curve was linearly related to dose. Plasma concentration-time curves normalised for dose were superimposable. It was concluded that over the dose range investigated, non-linear pharmacokinetic behavior had not been demonstrated in this group of normal volunteers.

    PMID:7437263 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1430141 Al-Habet S, Rogers HJ; Br J Clin Pharmacol 10 (5): 503-8 (1980)

    For more Absorption, Distribution and Excretion (Complete) data for PREDNISOLONE (13 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    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.

    Reduction of the 4,5 double bond can occur at both hepatic and extrahepatic sites and yields an inactive substance. Subsequent reduction of the 3-ketone substituent to a 3-hydroxyl to form tetrahydrocortisol has been demonstrated only in liver. Most of the ring a - reduced metabolites are enzymatically coupled through the 3-hydroxyl with sulfate or with glucuronic acid to form water soluble sulfate esters or glucuronides, and they are excreted as such.

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1446

    Conjugated mostly in liver but also in kidney. /Human, oral/

    American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1963

    In the present study the metabolism of prednisolone in the isolated, perfused, dual recirculating human placental lobule was reexamined, using a perfusate based on tissue culture medium 199. Four metabolites were identified in both the maternal and fetal compartments in 6 hr perfusions by comparison of relative retention times measured by HPLC and capillary GC and of mass spectra recorded by capillary GC/MS with those of authentic reference standards. The steroids were derivatized as the MO-TMS ethers for mass spectral measurements. Analysis of samples from five perfusion experiments resulted in the following percentage conversions after 6 hr perfusion (mean + or - standard deviation, maternal and fetal perfusate, respectively): prednisone (49.1 + or - 7.8, 49.1 + or - 6.6), 20 alpha-dihydroprednisone (0.84 + or - 0.29, 0.81 + or - 0.35), 20 beta-dihydroprednisone (39.1 + or - 6.7, 39.2 + or - 5.9), 20 beta-dihydroprednisolone (6.8 + or - 2.7, 6.3 + or - 1.6) and unmetabolized prednisolone (4.1 + or - 1.8, 4.6 + or - 2.1). No evidence was found for metabolites formed by 6 beta-hydroxylation or cleavage of the C17-C20 bond.

    PMID:2069869 Addison RS et al; J Steroid Biochem Mol Biol 39 (1): 83-90 (1991)

    A randomized, four-way cross-over study was conducted in eight healthy male volunteers to determine the relative and absolute bioavailability of prednisone (PN) and prednisolone (PL). PN and PL were administered as single, oral 10-mg tablet doses and as 10-mg zero-order 0.5-hour intravenous infusions. Comparable mean PN and PL maximum plasma concentrations (Cmax), times for Cmax, areas under the plasma concentration-time curves (AUC), and apparent elimination rate constants between tablet treatments demonstrated that PN and PL tablets were bioequivalent. Absolute bioavailability (F) determinations based on plasma PL concentrations were independent of which IV treatment was used as reference and indicated complete systemic availability of PL from both PN and PL tablets. However, F based on plasma PN data was contradictory. Using IV PN as reference, approximately 70% systemic availability was observed from both tablets, whereas using IV PL as reference, systemic availability was greater than unity. PN and PL are model compounds that exemplify the difficulties involved in accurately determining the relative and absolute bioavailability of substances that undergo reversible metabolism.

    PMID:3350994 Ferry JJ et al; J Clin Pharmacol 28(1):81-7 (1988)

    Prednisone, prednisolone, and methylprednisolone are currently administered in association with cyclosporin A in the postoperative treatment of transplant patients. The aim of this work was to evaluate the effects of these corticosteroids on the expression of several forms of cytochromes p450, including p450 1A2, 2D6, 2E1, and 3A, and on cyclosporin A oxidase activity in human liver. For this purpose, human hepatocytes prepared from lobectomies were maintained in culture in a serum-free medium, in collagen-coated dishes, for 96-144 hr, in the absence or presence of 50-100 uM corticosteroids, rifampicin, or dexamethasone. To mimic more closely the current clinical protocol, hepatocyte cultures were also co-treated with corticosteroids and cyclosporin A or ketoconazole (a selective inhibitor of cytochromes p450 3A). Cyclosporin A oxidase activity, intracellular retention of cyclosporin A oxidized metabolites within hepatocytes, accumulation of cytochromes p450 proteins and corresponding messages, and de novo synthesis and half-lives of these cytochromes p450 were measured in parallel in these cultures. Our results, obtained from seven different hepatocyte cultures, showed that 1) dexamethasone and prednisone, but not prednisolone or methylprednisolone, were inducers of cytochrome p450 3A, at the level of protein and mRNA accumulation, as well as of cyclosporin A oxidase activity, known to be predominantly catalyzed by these cytochromes p450; 2) although corticosteroids are known to be metabolized in human liver, notably by cytochrome p450 3A, partial or total inhibition of this cytochromes p450 by cyclosporin or ketoconazole, respectively, did not affect the inducing efficiency of these molecules; 3) corticosteroids did not affect the half-life of cytochrome p450 3A or the accumulation of other forms of cytochromes p450, including 1A2, 2D6, and 2E1; 4) chronic treatment of cells with cyclosporin did not affect cytochrome p450 3A accumulation; 5) corticosteroids were all competitive inhibitors of cyclosporin A oxidase in human liver microsomes, with Ki values of 61 + or - 12, 125 + or - 25, 190 + or - 38, and 210 + or - 42 uM for dexamethasone, prednisolone, prednisone, and methylprednisolone, respectively; and 6) chronic treatment of cells with corticosteroids did not influence the excretion of oxidized metabolites of cyclosporin from the cells.

    PMID:1614409 Pichard L et al; Mol Pharmacol 41 (6): 1047-55 (1992)

    5.7 Biological Half-Life

    Prednisolone has a plasma half life of 2.1-3.5 hours. This half life is shorter in children and longer in those with liver disease.

    ...Prednisolone (60 mg/sq m/day in three divided doses) was administered both orally and intravenously /to 23 children with acute lymphoblastic leukemia (ALL) (aged 2-15 years)/, and samples were obtained on several days during the initial 5 weeks of remission induction therapy. ...The median unbound clearance (32 L/hr/sq m) was lower, and the half-life (3.6 hr) longer than previously reported in childhood ALL.

    PMID:12698270 Petersen KB et al; Cancer Chemother Pharmacol 51 (6): 465-73 (2003)

    Doses of 16, 32, 48 and 64 mg prednisolone were administered intravenously to normal volunteers who also received 100 prednisolone orally. ...The mean T 1/2 over all doses were 4.11 +/- 0.97 (s.d.) hr and there was no evidence of a dose-related change in its value.

    PMID:7437263 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1430141 Al-Habet S, Rogers HJ; Br J Clin Pharmacol 10 (5): 503-8 (1980)

    5.8 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.

    Although altered homeostatic regulation, including disturbance of 24-h rhythms, is often observed in the patients undergoing glucocorticoid therapy, the mechanisms underlying the disturbance remains poorly understood. We report here that chronic treatment with a synthetic glucocorticoid, prednisolone, can cause alteration of circadian clock function at molecular level. Treatment of cultured hepatic cells (HepG2) with prednisolone induced expression of Period1 (Per1), and the prednisolone treatment also attenuated the serum-induced oscillations in the expression of Period2 (Per2), Rev-erbalpha, and Bmal1 mRNA in HepG2 cells. Because the attenuation of clock gene oscillations was blocked by pretreating the cells with a Per1 antisense phosphothioate oligodeoxynucleotide, the extensive expression of Per1 induced by prednisolone may have resulted in the reduced amplitude of other clock gene oscillations. Continuous administration of prednisolone into mice constitutively increased the Per1 mRNA levels in liver and skeletal muscle, which seems to attenuate the oscillation in the expressions of Per2, Rev-erbalpha, and Bmal1. However, a single daily administration of prednisolone at the time of day corresponding to acrophase of endogenous glucocorticoid levels had little effect on the rhythmic expression of clock genes. These results suggest a possible pharmacological action by prednisolone on the core circadian oscillation mechanism and indicate the possibility that the alteration of clock function induced by prednisolone can be avoided by optimizing the dosing schedule.

    PMID:16269518 Koyanagi S et al; Mol Endocrinol 20 (3): 573-83 (2006)

    Glucocorticoids are capable of suppressing the inflammatory process through numerous pathways. They interact with specific intracellular receptor proteins in target tissues to alter the expression of corticosteroid-responsive genes. Glucocorticoid-specific receptors in the cell cytoplasm bind with steroid ligands to form hormone-receptor complexes that eventually translocate to the cell nucleus. There these complexes bind to specific DNA sequences and alter their expression. The complexes may induce the transcription of mRNA leading to synthesis of new proteins. Such proteins include lipocortin, a protein known to inhibit PLA2a and thereby block the synthesis of prostaglandins, leukotrienes, and PAF. Glucocorticoids also inhibit the production of other mediators including AA metabolites such as COX, cytokines, the interleukins, adhesion molecules, and enzymes such as collagenase. /Glucocorticoids/

    Kahn, C.M. (Ed.); The Merck Veterinary Manual 9th ed. Merck & Co. Whitehouse Station, NJ. 2005, p. 2128

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    02-Jan-2021
    28-Oct-2024
    KGS
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