| Version |
2.5 |
| Creation Date |
2005-06-13 13:24:05 |
| Update Date |
2009-02-19 16:04:32 |
| Primary Accession Number |
DB00860 |
| Secondary Accession Number |
|
| Name |
Prednisolone |
| Drug Type |
|
| Description |
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. [PubChem] |
| Synonyms |
- Deltahydrocortisone
- Methylprednisolone Acetate
- PRDL
- Predisolone Sodium Phosphate
- Prednisolona [INN-Spanish]
- Prednisolone Acetate
- Prednisolone Sodium Phosphate
- Prednisolone Tebutate
- Prednisolonum [INN-Latin]
|
| Brand Names |
- Ak-Pred
- Ak-Tate
- Alphadrol
- Articulose-50
- Co-Hydeltra
- Codelcortone
- Cordrol
- Cortalone
- Cotogesic
- Cotolone
- Decaprednil
- Decortin H
- Delcortol
- Delta F
- Delta-Cortef
- Delta-Stab
- Deltacortenol
- Deltacortril
- Deltacortril Enteric
- Deltasolone
- Deltisilone
- Depo-Medrol
- Derpo Pd
- Dexa-Cortidelt Hostacortin H
- Di-Adreson F
- Dicortol
- Donisolone
- Dydeltrone
- Eazolin D
- Econopred
- Econopred Plus
- Erbacort
- Erbasona
- Estilsona
- Fernisolone
- Fernisolone P
- Fernisolone-P
- Flamasone
- Hostacortin H
- Hydeltra
- Hydeltra-Tba
- Hydeltrasol
- Hydeltrone
- Hydrodeltalone
- Hydrodeltisone
- Hydroretrocortin
- Hydroretrocortine
- I-Pred
- Inflamase Forte
- Inflamase Mild
- Key-Pred
- Klismacort
- Lentosone
- Lite Pred
- M-Predrol
- Medrol
- Medrol Acetate
- Metacortandralone
- Meti-Derm
- Meticortelone
- Metreton
- Nisolone
- Nor-Pred T.B.A.
- Ocu-Pred
- Ocu-Pred Forte
- Ophtho-Tate
- Orapred
- Panafcortelone
- Paracortol
- Paracotol
- Pediapred
- Precortalon
- Precortancyl
- Precortilon
- Precortisyl
- Pred Forte
- Pred Mild
- Predair
- Predair A
- Predair Forte
- Predalone 50
- Predalone T.B.A.
- Predate Tba
- Predate-50
- Predcor-25
- Predcor-50
- Predcor-Tba
- Predne-Dome
- Prednelan
- Predni-Dome
- Prednicen
- Predniliderm
- Predniretard
- Prednis
- Predonin
- Predonine
- Prelone
- Prenolone
- Rolisone
- Scherisolon
- Solone
- Steran
- Sterane
- Sterolone
- Supercortisol
- Ulacort
- Ultra Pred
- Ultracorten H
- Ultracortene H
- Ultracortene-H
- Ultracortene-Hydrogen
|
| Brand Mixtures |
- Ak Cide Oph Soln (Prednisolone Acetate + Sulfacetamide Sodium)
- Blephamide Oph Ont (Prednisolone Acetate + Sulfacetamide Sodium)
- Blephamide Opht Suspension (Prednisolone Acetate + Sulfacetamide Sodium)
- Canaural (Diethanolamine Fusidate + Framycetin Sulfate + Nystatin + Prednisolone)
- Chlorasone (Chloramphenicol + Prednisolone Acetate)
- Delta-Albaplex Tablets (Novobiocin (Novobiocin Sodium) + Prednisolone + Tetracycline Hydrochloride)
- Dioptimyd Ointment (Prednisolone Acetate + Sulfacetamide Sodium)
- Dioptimyd Suspension (Prednisolone Acetate + Sulfacetamide Sodium)
- Liquichlor (Chloramphenicol + Prednisolone + Squalane + Tetracaine)
- Metimyd Oph Sus (Prednisolone Acetate + Sulfacetamide Sodium)
- Optisone (Neomycin + Prednisolone)
- Pred C Tab (Aluminum Hydroxide + Prednisolone + Salicylamide + Vitamin C)
- Prednisize Solution (Camphor + Chlorophenol + Cresyl Acetate + Prednisolone)
- Quiex-Pred Sus (Aminophylline + Guaifenesin + Prednisolone)
- Surolan Drops (Miconazole Nitrate + Polymyxin B Sulfate + Prednisolone Acetate)
- Vanectyl-P Tablets (Prednisolone + Trimeprazine Tartrate)
- Vasocidin Ophthalmic Solution (Prednisolone Sodium Phosphate + Sulfacetamide Sodium)
|
| Chemical 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 |
| Chemical Formula |
C21H28O5 |
| Chemical Structure |
 |
| CAS Registry Number |
50-24-8 |
| InChI Identifier |
InChI=1/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 |
| InChI Key |
OIGNJSKKLXVSLS-VWUMJDOOBF |
| KEGG Drug |
D00472  |
| KEGG Compound |
C07369  |
| PubChem Compound |
5755  |
| PubChem Substance |
148534  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA451096  |
| HET ID |
DEX  |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
02245532  |
| RxList Link |
http://www.rxlist.com/cgi/generic/prednisolone.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Prednisolone  |
| FDA Label |
|
| Material Safety Data Sheet (MSDS) |
|
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
360.4440 |
| Monoisotopic Molecular Weight |
360.1937 |
| State |
Solid |
| Melting Point |
235 oC |
| Experimental Water Solubility |
223 mg/L
Source: PhysProp
|
| Predicted Water Solubility |
2.39e-01 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
1
Source: PhysProp
|
| Predicted LogP |
1.66
Calculated using ALOGPS
|
| Experimental LogS |
-3.21 [ADME Research, USCD] |
| Predicted LogS |
-3.18
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
Not Available |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
C[C@]12C[C@H](O)[C@H]3[C@@H](CCC4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO |
| Canonical SMILES |
CC12CC(O)C3C(CCC4=CC(=O)C=CC34C)C1CCC2(O)C(=O)CO |
| Drug Category |
- Adrenergic Agents
- Anti-inflammatory Agents
- Antineoplastic Agents
- Antineoplastic Agents, Hormonal
- Glucocorticoids
|
| ATC Codes |
|
| AHFS Codes |
|
| Indication |
For the treatment of primary or secondary adrenocortical insufficiency, such as congenital adrenal hyperplasia, thyroiditis. Also used to treat psoriatic arthritis, rheumatoid arthritis, ankylosing spondylitis, bursitis, acute gouty arthritis and epicondylitis. Also indicated for treatment of systemic lupus erythematosus, pemphigus and acute rhematic carditis. Can be used in the treatment of leukemias, lymphomas, thrombocytopenia purpura and autoimmune hemolytic anemia. Can be used to treat celiac disease, insulin resistance, ulcerative colitis and liver disorders. |
| Pharmacology |
Prednisolone is a synthetic glucocorticoid used as antiinflammatory or immunosuppressive agent. Prednisolone is indicated in the treatment of various conditions, including congenital adrenal hyperplasia, psoriatic arthritis, systemic lupus erythematosus, bullous dermatitis herpetiformis, seasonal or perennial allergic rhinitis, allergic corneal marginal ulcers, symptomatic sarcoidosis, idiopathic thrombocytopenic purpura in adults, leukemias and lymphomas in adults, and ulcerative colitis. Glucocorticoids are adrenocortical steroids and cause profound and varied metabolic effects. In addition, they modify the body's immune responses to diverse stimuli. |
| Mechanism of Action |
Glucocorticoids such as Prednisolone 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. Prednisolone 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. Prednisolone 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. |
| Absorption |
Readily absorbed by gastrointestinal tract, peak plasma concentration is reached 1-2 hours after administration. |
| Toxicity |
LD50=500 mg/kg (oral, rat), short-term side effects include high blood glucose levels and fluid retention. Long term side effects include Cushing's syndrome, weight gain, osteoporosis, glaucoma, type II diabetes and adrenal suppression. |
| Protein Binding |
Very high (>90%) |
| Biotransformation |
Excreted in the urine as either free or glucoconjugate. |
| Half Life |
2-3 hours |
| Dosage Forms |
| Form |
Route |
| Liquid |
Oral |
| Solution |
Oral |
| Solution / drops |
Ophthalmic |
| Suspension |
Ophthalmic |
| Tablet |
Oral |
|
| Patient Information |
Show  |
| Contraindications |
Show  |
| Interactions |
Not Available |
| Drug Interactions |
| Drug |
Interaction |
| Acenocoumarol |
The corticosteroid alters the anticoagulant effect |
| Ambenonium |
The corticosteroid decreases the effect of anticholinesterases |
| Amobarbital |
The barbiturate decreases the effect of the corticosteroid |
| Anisindione |
The corticosteroid alters the anticoagulant effect |
| Aprobarbital |
The barbiturate decreases the effect of the corticosteroid |
| Aspirin |
The corticosteroid decreases the effect of salicylates |
| Bismuth Subsalicylate |
The corticosteroid decreases the effect of salicylates |
| Butabarbital |
The barbiturate decreases the effect of the corticosteroid |
| Butalbital |
The barbiturate decreases the effect of the corticosteroid |
| Butethal |
The barbiturate decreases the effect of the corticosteroid |
| Chlorotrianisene |
The estrogenic agent increases the effect of the corticosteroid |
| Clomifene |
The estrogenic agent increases the effect of the corticosteroid |
| Conjugated Estrogens |
The estrogenic agent increases the effect of the corticosteroid |
| Dicumarol |
The corticosteroid alters the anticoagulant effect |
| Diethylstilbestrol |
The estrogenic agent increases the effect of the corticosteroid |
| Dihydroquinidine barbiturate |
The barbiturate decreases the effect of the corticosteroid |
| Edrophonium |
The corticosteroid decreases the effect of anticholinesterases |
| Estradiol |
The estrogenic agent increases the effect of the corticosteroid |
| Estriol |
The estrogenic agent increases the effect of the corticosteroid |
| Estrone |
The estrogenic agent increases the effect of the corticosteroid |
| Estropipate |
The estrogenic agent increases the effect of the corticosteroid |
| Ethinyl Estradiol |
The estrogenic agent increases the effect of the corticosteroid |
| Ethotoin |
The enzyme inducer decreases the effect of the corticosteroid |
| Fosphenytoin |
The enzyme inducer decreases the effect of the corticosteroid |
| Heptabarbital |
The barbiturate decreases the effect of the corticosteroid |
| Hexobarbital |
The barbiturate decreases the effect of the corticosteroid |
| Itraconazole |
The imidazole increases the effect and toxicity of the corticosteroid |
| Ketoconazole |
The imidazole increases the effect and toxicity of the corticosteroid |
| Mephenytoin |
The enzyme inducer decreases the effect of the corticosteroid |
| Mestranol |
The estrogenic agent increases the effect of the corticosteroid |
| Methohexital |
The barbiturate decreases the effect of the corticosteroid |
| Methylphenobarbital |
The barbiturate decreases the effect of the corticosteroid |
| Midodrine |
Increased arterial pressure |
| Neostigmine |
The corticosteroid decreases the effect of anticholinesterases |
| Pentobarbital |
The barbiturate decreases the effect of the corticosteroid |
| Phenobarbital |
The barbiturate decreases the effect of the corticosteroid |
| Phenytoin |
The enzyme inducer decreases the effect of the corticosteroid |
| Primidone |
The barbiturate decreases the effect of the corticosteroid |
| Pyridostigmine |
The corticosteroid decreases the effect of anticholinesterases |
| Quinestrol |
The estrogenic agent increases the effect of the corticosteroid |
| Quinidine barbiturate |
The barbiturate decreases the effect of the corticosteroid |
| Rifampin |
The enzyme inducer decreases the effect of the corticosteroid |
| Salicylate-magnesium |
The corticosteroid decreases the effect of salicylates |
| Salicylate-sodium |
The corticosteroid decreases the effect of salicylates |
| Salsalate |
The corticosteroid decreases the effect of salicylates |
| Secobarbital |
The barbiturate decreases the effect of the corticosteroid |
| Talbutal |
The barbiturate decreases the effect of the corticosteroid |
| Trisalicylate-choline |
The corticosteroid decreases the effect of salicylates |
| Warfarin |
The corticosteroid alters the anticoagulant effect |
|
| Food Interactions |
- Avoid alcohol. Avoid caffeine.
- Take with food to reduce gastric irritation.
|
| Pathways |
Not Available
|
| General References |
- Drugs.com

- Wikipedia

- RxList

|
| Organisms Affected |
|
| Phase 1 Metabolizing Enzymes |
- Cytochrome P450 3A4 (CYP3A4)
|
| Targets |
- Corticosteroid-binding globulin
|
|
Drug Target 1
[top]
|
| Target 1 ID |
232 |
| Target 1 Name |
Corticosteroid-binding globulin |
| Target 1 Synonyms |
- CBG
- Corticosteroid-binding globulin precursor
- Serpin A6
- Transcortin
|
| Target 1 Gene Name |
SERPINA6 |
| Target 1 Protein Sequence |
>Corticosteroid-binding globulin precursor
MPLLLYTCLLWLPTSGLWTVQAMDPNAAYVNMSNHHRGLASANVDFAFSLYKHLVALSPK
KNIFISPVSISMALAMLSLGTCGHTRAQLLQGLGFNLTERSETEIHQGFQHLHQLFAKSD
TSLEMTMGNALFLDGSLELLESFSADIKHYYESEVLAMNFQDWATASRQINSYVKNKTQG
KIVDLFSGLDSPAILVLVNYIFFKGTWTQPFDLASTREENFYVDETTVVKVPMMLQSSTI
SYLHDSELPCQLVQMNYVGNGTVFFILPDKGKMNTVIAALSRDTINRWSAGLTSSQVDLY
IPKVTISGVYDLGDVLEEMGIADLFTNQANFSRITQDAQLKSSKVVHKAVLQLNEEGVDT
AGSTGVTLNLTSKPIILRFNQPFIIMIFDHFTWSSLFLARVMNPV
|
| Target 1 Number of Residues |
411 |
| Target 1 Molecular Weight |
45141 |
| Target 1 Theoretical pI |
5.94 |
| Target 1 GO Classification |
|
Function
|
enzyme regulator activity
enzyme inhibitor activity
protease inhibitor activity
endopeptidase inhibitor activity
serine-type endopeptidase inhibitor activity |
|
Process
|
| Not Available |
|
Component
|
| Not Available |
|
| Target 1 General Function |
Involved in serine-type endopeptidase inhibitor activity |
| Target 1 Specific Function |
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species |
| Target 1 Pathways |
Not Available
|
| Target 1 Reactions |
Not Available |
| Target 1 Pfam Domain Function |
|
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
|
| Target 1 Essentiality |
Non-Essential |
| Target 1 GenBank ID Protein |
179971  |
| Target 1 UniProtKB/Swiss-Prot ID |
P08185  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
CBG_HUMAN  |
| Target 1 PDB ID |
Not Available |
| Target 1 Cellular Location |
|
| Target 1 Gene Sequence |
>1218 bp
ATGCCACTCCTCCTGTACACCTGTCTTCTCTGGCTGCCCACCAGCGGCCTCTGGACCGTC
CAGGCCATGGATCCTAACGCTGCTTATGTGAACATGAGTAACCATCACCGGGGCCTGGCT
TCAGCCAACGTTGACTTTGCCTTCAGCCTGTATAAGCACCTAGTGGCCTTGAGTCCCAAA
AAGAACATTTTCATCTCCCCTGTGAGCATCTCCATGGCCTTAGCTATGCTGTCCCTGGGC
ACCTGTGGCCACACACGGGCCCAGCTTCTCCAGGGCCTGGGTTTCAACCTCACTGAGAGG
TCTGAGACTGAGATCCACCAGGGTTTCCAGCACCTGCACCAACTCTTTGCAAAGTCAGAC
ACCAGCTTAGAAATGACTATGGGCAATGCCTTGTTTCTTGATGGCAGCCTGGAGTTGCTG
GAGTCATTCTCAGCAGACATCAAGCACTACTATGAGTCAGAGGTCTTGGCTATGAATTTC
CAGGACTGGGCAACAGCCAGCAGACAGATCAACAGCTATGTCAAGAATAAGACACAGGGG
AAAATTGTCGACTTGTTTTCAGGGCTGGATAGCCCAGCCATCCTCGTCCTGGTCAACTAT
ATCTTCTTCAAAGGCACATGGACACAGCCCTTTGACCTGGCAAGCACCAGGGAGGAGAAC
TTCTATGTGGACGAGACAACTGTGGTGAAGGTGCCCATGATGTTGCAGTCGAGCACCATC
AGTTACCTTCATGACTCAGAGCTCCCCTGCCAGCTGGTGCAGATGAACTACGTGGGCAAT
GGGACTGTCTTCTTCATCCTTCCGGACAAGGGGAAGATGAACACAGTCATCGCTGCACTG
AGCCGGGACACGATTAACAGGTGGTCCGCAGGCCTGACCAGCAGCCAGGTGGACCTGTAC
ATTCCAAAGGTCACCATCTCTGGAGTCTATGACCTTGGAGATGTGCTGGAGGAAATGGGC
ATTGCAGACTTGTTCACCAACCAGGCAAATTTCTCACGCATCACCCAGGACGCCCAGCTG
AAGTCATCAAAGGTGGTCCATAAAGCTGTGCTGCAACTCAATGAGGAGGGTGTGGACACA
GCTGGCTCCACTGGGGTCACCCTAAACCTGACGTCCAAGCCTATCATCTTGCGTTTCAAC
CAGCCCTTCATCATCATGATCTTCGACCACTTCACCTGGAGCAGCCTTTTCCTGGCGAGG
GTTATGAACCCAGTGTAA
|
| Target 1 GenBank Gene ID |
|
| Target 1 GeneCard ID |
SERPINA6  |
| Target 1 GenAtlas ID |
SERPINA6  |
| Target 1 HGNC ID |
HGNC:1540  |
| Target 1 Chromosome Location |
14 |
| Target 1 Locus |
14q32.1 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- Emptoz-Bonneton A, Cousin P, Seguchi K, Avvakumov GV, Bully C, Hammond GL, Pugeat M: Novel human corticosteroid-binding globulin variant with low cortisol-binding affinity. J Clin Endocrinol Metab. 2000 Jan;85(1):361-7. [PubMed
]
- Smith CL, Power SG, Hammond GL: A Leu----His substitution at residue 93 in human corticosteroid binding globulin results in reduced affinity for cortisol. J Steroid Biochem Mol Biol. 1992 Aug;42(7):671-6. [PubMed
]
- Hammond GL, Smith CL, Goping IS, Underhill DA, Harley MJ, Reventos J, Musto NA, Gunsalus GL, Bardin CW: Primary structure of human corticosteroid binding globulin, deduced from hepatic and pulmonary cDNAs, exhibits homology with serine protease inhibitors. Proc Natl Acad Sci U S A. 1987 Aug;84(15):5153-7. [PubMed
]
- Kato EA, Hsu BR, Kuhn RW: Comparative structural analyses of corticosteroid binding globulin. J Steroid Biochem. 1988 Feb;29(2):213-20. [PubMed
]
- Bardin CW, Gunsalus GL, Musto NA, Cheng CY, Reventos J, Smith C, Underhill DA, Hammond G: Corticosteroid binding globulin, testosterone-estradiol binding globulin, and androgen binding protein belong to protein families distinct from steroid receptors. J Steroid Biochem. 1988;30(1-6):131-9. [PubMed
]
- Van Baelen H, Power SG, Hammond GL: Decreased cortisol-binding affinity of transcortin Leuven is associated with an amino acid substitution at residue-93. Steroids. 1993 Jun;58(6):275-7. [PubMed
]
|
| Target 1 Drug References |
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed
]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed
]
- Angeli A, Frajria R, De Paoli R, Fonzo D, Ceresa F: Diurnal variation of prednisolone binding to serum corticosteroid-binding globulin in man. Clin Pharmacol Ther. 1978 Jan;23(1):47-53. [PubMed
]
- Frey BM, Frey FJ: Estimation of transcortin concentration by measurements of plasma protein-binding of prednisolone and by electroimmunodiffusion. Br J Clin Pharmacol. 1982 Feb;13(2):245-9. [PubMed
]
- Ko HC, Almon RR, Jusko WJ: Effect of corticosteroid binding globulin on the pharmacokinetics of prednisolone in rats. Pharm Res. 1995 Jun;12(6):902-4. [PubMed
]
|