CAS 50-24-8|Prednisolone|11β, 17α, 21-Trihydroxypregna-1,4-diene-3,20-dione|(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...

General Information

Structure

Molecular Formula

C₂₁H₂₈O₅

Molecular Mass

360.44402

Exact Mass

360.193674

Charge

0

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

InChIKey

OIGNJSKKLXVSLS-VWUMJDOOSA-N

Canonic Smiles

OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C

Isomeric Smiles

O[C@]1([C@@]2([C@H]([C@H]3[C@H]([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)CC3)C)CC1)C)C(=O)CO

Calculated Properties

JChem

LogD (pH = 7.4)

1.27

LogD (pH = 5.5)

1.27

Log P

1.27

Rotatable Bonds

2

H Donor

3

H Acceptors

5

Lipinski's Rule of Five

true

Acid pKa

12.59

Polar Surface Area

94.83

Polarizability

38.74

Molar Refractivity

98.49

LOG S

-3.46

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

Prednisolone11β, 17α, 21-Trihydroxypregna-1,4-diene-3,20-dione1,4-Pregnadiene-11β,17α,21-triol-3,20-dione1-Dehydrohydrocortisone1-DehydrocortisolPrednisolonum [INN-Latin]Methylprednisolone AcetatePrednisolona [INN-Spanish]Prednisolone TebutatePredisolone Sodium PhosphatePrednisolone AcetatePrednisolone Sodium PhosphateDeltahydrocortisonePRDLHydroretrocortinePredonine1-去氢皮质醇Prednisolone(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-one1,4-孕甾二烯-11β,17α,21-三醇-3,20-二酮11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮泼尼松龙1-去氢氢化可的松Decaprednil1,4-Pregnadiene-11β,17α,21-triol-3,20-dione11β,17α,21-Trihydroxy-1,4-pregnadiene-3,20-dioneHydeltraDelta-Cortef(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-onemetacortandralonehydroretrocortineDelta(1)-dehydrohydrocortisone(11beta)-11,17,21-trihydroxypregna-1,4-diene-3,20-dioneprednisolone3,20-dioxo-11beta,17alpha,21-trihydroxy-1,4-pregnadiene1,4-pregnadiene-3,20-dione-11beta,17alpha,21-triolDelta(1)-dehydrocortisolDelta(1)-hydrocortisone1,4-pregnadiene-11beta,17alpha,21-triol-3,20-dione

IUPAC name

(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 (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one (1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one

IUPAC Traditional name

prednisolone (1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one

Brand Name

CotolonePred ForteAk-TatePrenoloneFlamasoneDydeltroneErbasonaPrednilidermArticulose-50DicortolDelta-CortefPredcor-50MetretonPediapredFernisoloneDecortin HDeltasoloneFernisolone PI-PredKlismacortAlphadrolUltra PredNor-Pred T.B.A.M-PredrolEconopredPrednicenHydeltraLite PredDeltacortril EntericFernisolone-PUltracortene HPredcor-25SteraneDeltacortenolHydroretrocortinKey-PredErbacortPrecortisylPredalone T.B.A.Inflamase ForteOphtho-TateEazolin DPredne-DomeParacotolPrecortilonPredalone 50Delta FDeltisilonePredate-50RolisonePrecortancylPrednelanHydrodeltaloneMedrol AcetateEstilsonaPredair FortePredoninDexa-Cortidelt Hostacortin HDi-Adreson FPredcor-TbaInflamase MildUlacortPrednisPred MildMeti-DermMeticorteloneNisoloneCordrolOrapredPreloneOcu-PredPredairHydeltroneLentosoneCo-HydeltraPredate TbaPredni-DomeMetacortandraloneOcu-Pred FortePanafcorteloneHydeltra-TbaPredonineHydeltrasolScherisolonParacortolPredniretardDepo-MedrolSteroloneDelta-StabHydrodeltisoneEconopred PlusCortaloneCotogesicDeltacortrilUltracorten HUltracortene-HSoloneSteranPrecortalonPredair AHydroretrocortineMedrolDecaprednilUltracortene-HydrogenAk-PredSupercortisolDelcortolHostacortin HDerpo PdDonisoloneCodelcortone

API Name

Prednisolone

International Nonproprietary Name (INN)

prednisolonaprednisoloneprednisolonum

Names and Identifiers

Registration numbers

PubChem SID

4650484716096420124870351248980792489872526697414

PubChem CID

CAS Number

EC Number

MDL Number

Beilstein Number

DrugBank ID

BKMS React Database

Patent number

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

BRENDA Database

1.1.1.1411.3.99.41.1.1.1461.3.1.34.2.1.21.1.1.501.1.1.2131.14.15.8

Reaxys Registry

1354103

ArrayExpress (Gene Expression Altlas)

E-MTAB-3671E-GEOD-21048E-MTAB-5235

MetaboLights Database

MTBLS2096MTBLS2145MTBLS3487MTBLS407MTBLS1918MTBLS136MTBLS3750MTBLS2406MTBLS220MTBLS205

MassBank Database

EA278302EA278311EA278314EA278305EA278310EA278303EA278312EA278307EA278309EA278313EA278304EA278306EA278301EA278308

BRENDA Ligand Database

SABIO-RK Database

CHEBI ID

HMDB Database

NURSA Database

10.1621/PJyuUZbBuO10.1621/kNaE74Iapu

Protein Data Bank

6w9k

PubMed Citation Links

243927642362598211294518

CHEMBL

CHEMBL131

Drug Central Database

Wikipedia Title

CompTox Database

KEGG ID

BindingDB Database

KEGG DRUG Database

SureChEMBL Database

VSDB Database

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... AR(367), ESR1(2099), NR3C1(2908), NR3C2(4306), PGR(5241), SERPINA6(866)mouse ... Nr3c1(14815)rat ... Ar(24208)

Mechanism of Action

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.

Glucocorticoid receptor agonist.

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.

Properties

Related Proteins

PDB Bank

6W9K

Related Proteins

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00860

Drug Groups

approved

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]

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.

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.

Affected Organisms

Humans and other mammals

Biotransformation

Excreted in the urine as either free or glucoconjugate.

Absorption

Readily absorbed by gastrointestinal tract, peak plasma concentration is reached 1-2 hours after administration.

Half Life

2-3 hours

Protein Binding

Very high (>90%)

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1737

Research Area: Inflammation
Biological Activity:
Prednisolone(Hydroretrocortine) is a synthetic glucocorticoid with anti-inflammatory and immunomodulating properties. After cell surface receptor attachment and cell entry, prednisolone enters the nucleus where it binds to and activates specific nuclear receptors, resulting in an altered gene expression and inhibition of proinflammatory cytokine production. This agent also decreases the number of circulating lymphocytes, induces cell differentiation, and stimulates apoptosis in sensitive tumor cells populations. [1,2]

MP Biomedicals

02102717

Crystalline

Sigma Aldrich

P0152

包装
Supplied in amber screw-cap vials

P6004

Analysis Note
Actual content given on label
Biochem/physiol Actions
Prednisolone is a glucocorticoid with anti-inflammatory and immunosuppressive activity.
包装
1, 5, 10, 25 g in poly bottle
100 mg in poly bottle

46656

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

ChEBI

CHEBI:8378

A glucocorticoid that is prednisone in which the oxo group at position 11 has been reduced to the corresponding beta-hydroxy group. It is a drug metabolite of prednisone.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Prednisolone

• Ali, S.L., Anal. Profiles Drug Subst., 1992, 21, 415, (rev)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AAF625; PMA000; PMA100; SOV100; PLY300

• Kirk, D.N. et al., J.C.S. Perkin 2, 1990, 1567, (pmr)

• Zicha, L. et al., Arzneim.-Forsch., 1960, 10, 728; 831, (pharmacol, derivs)

• Jusko, W.J. et al., Ther. Drug Monit., 1980, 2, 169, (rev, pharmacol)

• Gonzalez, M.D. et al., Org. Magn. Reson., 1984, 22, 586, (cmr)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6297; 6321; 6941

• Herzog, H.L. et al., Tetrahedron, 1962, 18, 581, (synth)

• Toft, P. et al., Can. J. Spectrosc., 1970, 15, 137, (ms)

• Gambertoglis, J.G. et al., J. Pharmacokinet. Biopharm., 1980, 8, 1, (rev, pharmacol)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 585B, (nmr)

• Nobile, A. et al., J.A.C.S., 1955, 77, 4184, (biosynth)

• Herzog, H.L. et al., Science (Washington, D.C.), 1955, 121, 176, (struct)

• Hirschmann, R. et al., J.A.C.S., 1964, 86, 3903, (synth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 737

References

Bioactivity

PubChem BioAssay

Bioactivity

Molecule

ID:738