Prednisolone

Basic Info

Common NamePrednisolone(F05684)
2D Structure
FRCD IDF05684
CAS Number50-24-8
PubChem CID5755
FormulaC21H28O5
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

InChI Key

OIGNJSKKLXVSLS-VWUMJDOOSA-N

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

Canonical SMILES

CC12CC(C3C(C1CCC2(C(=O)CO)O)CCC4=CC(=O)C=CC34C)O

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

Synonyms
        
            Deltahydrocortisone
        
            prednisolone
        
            50-24-8
        
            Metacortandralone
        
            Hydroretrocortine
        
            Predonine
        
            Deltacortril
        
            Meticortelone
        
            Prenolone
        
            Hydroretrocortin
Classifies
                

                  
                    Predicted: Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
SubclassHydroxysteroids
Intermediate Tree NodesNot available
Direct Parent21-hydroxysteroids
Alternative Parents
Molecular FrameworkAliphatic homopolycyclic compounds
SubstituentsProgestogin-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
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight360.45
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Complexity724
Monoisotopic Mass360.194
Exact Mass360.194
XLogP1.6
Formal Charge0
Heavy Atom Count26
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9383
Human Intestinal AbsorptionHIA+0.9918
Caco-2 PermeabilityCaco2-0.5096
P-glycoprotein SubstrateSubstrate0.7861
P-glycoprotein InhibitorNon-inhibitor0.7847
Non-inhibitor0.8383
Renal Organic Cation TransporterNon-inhibitor0.7463
Distribution
Subcellular localizationMitochondria0.8362
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8496
CYP450 2D6 SubstrateNon-substrate0.9138
CYP450 3A4 SubstrateSubstrate0.7407
CYP450 1A2 InhibitorNon-inhibitor0.9406
CYP450 2C9 InhibitorNon-inhibitor0.9072
CYP450 2D6 InhibitorNon-inhibitor0.9418
CYP450 2C19 InhibitorNon-inhibitor0.9253
CYP450 3A4 InhibitorNon-inhibitor0.8902
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9095
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9500
Non-inhibitor0.5840
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.9597
Fish ToxicityHigh FHMT0.9833
Tetrahymena Pyriformis ToxicityHigh TPT0.9848
Honey Bee ToxicityHigh HBT0.7998
BiodegradationNot ready biodegradable0.9250
Acute Oral ToxicityIII0.7997
Carcinogenicity (Three-class)Non-required0.7360
Model Value Unit
Absorption
Aqueous solubility-3.0321LogS
Caco-2 Permeability0.8616LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8914LD50, mol/kg
Fish Toxicity1.0228pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.9935pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0.0007ppm
Other Aquatic AnimalJapan0.0007ppm
CrustaceansJapan0.0007ppm
Shelled MolluscasJapan0.0007ppm
Other FishJapan0.0007ppm
PerciformesJapan0.0007ppm
AnguilliformesJapan0.0007ppm
SalmoniformesJapan0.0007ppm
Other Poultry,EggsJapan0.0007ppm
Chicken,EggsJapan0.0007ppm
Other Poultry Animals,Edible OffalJapan0.0007ppm
Chicken,Edible OffalJapan0.0007ppm
Other Poultry Animals,KidneyJapan0.0007ppm
Chicken,KidneyJapan0.0007ppm
Other Poultry Animals,LiverJapan0.0007ppm
Chicken,LiverJapan0.0007ppm
Other Poultry Animals,FatJapan0.0007ppm
Chicken,FatJapan0.0007ppm
Other Poultry Animals,MuscleJapan0.0007ppm
Chicken,MuscleJapan0.0007ppm

References

TitleJournalDatePubmed ID
Differential somatic cell count in milk before, during, and after lipopolysaccharide- and lipoteichoic-acid-induced mastitis in dairy cows.J Dairy Sci2018 Jun29550141
Bovine teeth as a novel matrix for the control of the food chain: liquidchromatography-tandem mass spectrometry detection of treatments withprednisolone, dexamethasone, estradiol, nandrolone and seven β2-agonists.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Jan27845609
Broad spectrum pesticide application alters natural enemy communities and mayfacilitate secondary pest outbreaks.PeerJ2017 Dec 1929302395
Otitis media with effusion in the boxer: a report of seven cases.J Small Anim Pract2017 Dec 1229231979
TRIENNIAL LACTATION SYMPOSIUM/BOLFA: Pathogen-specific immune response and changes in the blood-milk barrier of the bovine mammary gland.J Anim Sci2017 Dec29293747
Guidelines for the Management of Atopic Dermatitis in Singapore.Ann Acad Med Singapore2016 Oct27832218
The other side of vitamin D therapy: 
a case series of acute kidney injury due to malpractice-related vitamin D intoxication
.Clin Nephrol2016 Nov27719737
Toxic epidermal necrolysis caused by acetaminophen featuring almost 100% skin detachment: Acetaminophen is associated with a risk of severe cutaneous adverse reactions.J Dermatol2016 Mar26362011
Progress in pediatrics in 2015: choices in allergy, endocrinology,gastroenterology, genetics, haematology, infectious diseases, neonatology,nephrology, neurology, nutrition, oncology and pulmonology.Ital J Pediatr2016 Aug 2727566421
Behavioural changes in dogs treated with corticosteroids.Physiol Behav2015 Nov 126344646
More Cercospora Species Infect Soybeans across the Americas than Meets the Eye.PLoS One2015 Aug 726252018
Effect-based detection of synthetic glucocorticoids in bovine urine.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201525569131
Effect of oral administration of metronidazole or prednisolone on fecalmicrobiota in dogs.PLoS One2014 Sep 1725229475
Moderate zinc supplementation during prolonged steroid therapy exacerbates boneloss in rats.Biol Trace Elem Res2014 Sep25022244
The clinical efficacy of dietary fat restriction in treatment of dogs withintestinal lymphangiectasia.J Vet Intern Med2014 May-Jun24673630
Effect of intramammary administration of prednisolone on the blood-milk barrier during the immune response of the mammary gland to lipopolysaccharide.Am J Vet Res2014 Jun24866517
Impact of intramammary treatment on gene expression profiles in bovineEscherichia coli mastitis.PLoS One2014 Jan 1424454893
Detection of boldenone, its conjugates and androstadienedione, as well as fivecorticosteroids in bovine bile through a unique immunoaffinity column clean-upand two validated liquid chromatography-tandem mass spectrometry analyses.Anal Chim Acta2014 Dec 1025441890
Protective effects of certain pharmaceutical compounds against abrin induced cell death in Jurkat cell line.Int Immunopharmacol2014 Aug24938881
Fast and multiresidue determination of twenty glucocorticoids in bovine milkusing ultra high performance liquid chromatography-tandem mass spectrometry.J Chromatogr A2013 Jun 1423643098