ChemFOnt: Showing chemical card for Prednisolone (CFc000009313)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:25 UTC

Chemfont ID

CFc000009313

Molecule Identification

Common Name

Prednisolone

Definition

Prednisolone is only found in individuals that have used or taken this drug. It is 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]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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(11beta)-11,17,21-Trihydroxypregna-1,4-diene-3,20-dione	ChEBI
1,4-Pregnadiene-11beta,17alpha,21-triol-3,20-dione	ChEBI
1,4-Pregnadiene-3,20-dione-11beta,17alpha,21-triol	ChEBI
3,20-Dioxo-11beta,17alpha,21-trihydroxy-1,4-pregnadiene	ChEBI
Delta(1)-Dehydrocortisol	ChEBI
Delta(1)-Dehydrohydrocortisone	ChEBI
Delta(1)-Hydrocortisone	ChEBI
Hydroretrocortine	ChEBI
Metacortandralone	ChEBI
Prednisolona	ChEBI
Prednisolonum	ChEBI
Delta-Cortef	Kegg
(11b)-11,17,21-Trihydroxypregna-1,4-diene-3,20-dione	Generator
(11Β)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione	Generator
1,4-Pregnadiene-11b,17a,21-triol-3,20-dione	Generator
1,4-Pregnadiene-11β,17α,21-triol-3,20-dione	Generator
1,4-Pregnadiene-3,20-dione-11b,17a,21-triol	Generator
1,4-Pregnadiene-3,20-dione-11β,17α,21-triol	Generator
3,20-Dioxo-11b,17a,21-trihydroxy-1,4-pregnadiene	Generator
3,20-Dioxo-11β,17α,21-trihydroxy-1,4-pregnadiene	Generator
Δ(1)-dehydrocortisol	Generator
Δ(1)-dehydrohydrocortisone	Generator
Δ(1)-hydrocortisone	Generator
Δ-cortef	Generator
Deltahydrocortisone	HMDB
Methylprednisolone acetate	HMDB
PRDL	HMDB
Predisolone sodium phosphate	HMDB
Prednisolone acetate	HMDB
Prednisolone sodium phosphate	HMDB
Prednisolone tebutate	HMDB
Di-adreson-F	HMDB
DiAdresonF	HMDB
Predate	HMDB
Predonine	HMDB
Di adreson F	HMDB

Chemical Formula

C₂₁H₂₈O₅

Average Molecular Weight

360.444

Monoisotopic Molecular Weight

360.193674006

IUPAC Name

(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

Traditional Name

prednisolone

CAS Registry Number

50-24-8

SMILES

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

InChI Identifier

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

InChI Key

OIGNJSKKLXVSLS-VWUMJDOOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-hydroxysteroids

Alternative Parents

Substituents

Progestogin-skeleton
21-hydroxysteroid
20-oxosteroid
Pregnane-skeleton
3-oxo-delta-1,4-steroid
3-oxosteroid
Oxosteroid
11-beta-hydroxysteroid
11-hydroxysteroid
17-hydroxysteroid
Delta-1,4-steroid
Cyclic alcohol
Tertiary alcohol
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Cyclic ketone
Primary alcohol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:8378 )
17alpha-hydroxy steroid (CHEBI:8378 )
glucocorticoid (CHEBI:8378 )
20-oxo steroid (CHEBI:8378 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:8378 )
21-hydroxy steroid (CHEBI:8378 )
Pregnane and derivatives [Fig] (C07369 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030179 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014998)
Kidney (HMDB: HMDB0014998)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014998)

Endogenous

Endogenous (HMDB: HMDB0014998)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Prednisone Action Pathway (PathBank: SMP0000440)
Prednisolone Action Pathway (PathBank: SMP0000441)

Metabolic pathway

Prednisone Metabolism Pathway (PathBank: SMP0000631)
Prednisolone Metabolism Pathway (PathBank: SMP0000632)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.24 g/L	ALOGPS
logP	1.66	ALOGPS
logP	1.27	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.49 m³·mol⁻¹	ChemAxon
Polarizability	38.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon