Methylprednisolone

Basic Info

Common NameMethylprednisolone(F05710)
2D Structure
FRCD IDF05710
CAS Number83-43-2
PubChem CID6741
FormulaC22H30O5
IUPAC Name

(6S,8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-6,10,13-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one

InChI Key

VHRSUDSXCMQTMA-PJHHCJLFSA-N

InChI

InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1

Canonical SMILES

CC1CC2C3CCC(C3(CC(C2C4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O

Isomeric SMILES

C[C@H]1C[C@H]2[C@@H]3CC[C@@]([C@]3(C[C@@H]([C@@H]2[C@@]4(C1=CC(=O)C=C4)C)O)C)(C(=O)CO)O

Synonyms
        
            Methylprednisolon
        
            methylprednisolone
        
            Medrol
        
            83-43-2
        
            Medrone
        
            Urbason
        
            6alpha-Methylprednisolone
        
            Metilbetasone
        
            Medrate
        
            Metilprednisolone
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 Weight374.477
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count2
Complexity754
Monoisotopic Mass374.209
Exact Mass374.209
XLogP1.9
Formal Charge0
Heavy Atom Count27
Defined Atom Stereocenter Count8
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+0.9484
Human Intestinal AbsorptionHIA+0.9911
Caco-2 PermeabilityCaco2-0.6404
P-glycoprotein SubstrateSubstrate0.7812
P-glycoprotein InhibitorNon-inhibitor0.7489
Non-inhibitor0.6040
Renal Organic Cation TransporterNon-inhibitor0.7690
Distribution
Subcellular localizationMitochondria0.8116
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8415
CYP450 2D6 SubstrateNon-substrate0.9115
CYP450 3A4 SubstrateSubstrate0.7582
CYP450 1A2 InhibitorNon-inhibitor0.9473
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9513
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9167
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9459
Non-inhibitor0.5985
AMES ToxicityNon AMES toxic0.9337
CarcinogensNon-carcinogens0.9529
Fish ToxicityHigh FHMT0.9832
Tetrahymena Pyriformis ToxicityHigh TPT0.9951
Honey Bee ToxicityHigh HBT0.8201
BiodegradationNot ready biodegradable0.9492
Acute Oral ToxicityIII0.8017
Carcinogenicity (Three-class)Non-required0.7338
Model Value Unit
Absorption
Aqueous solubility-3.2437LogS
Caco-2 Permeability0.9128LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.0025LD50, mol/kg
Fish Toxicity0.9455pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0706pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.01ppm
MilkUnited States10ppb
Cattle,Edible OffalJapan0.01ppm
Cattle,KidneyJapan0.01ppm
Cattle,LiverJapan0.01ppm
Cattle,FatJapan0.01ppm
Cattle,MuscleJapan0.01ppm

References

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Immune-mediated responses account for the majority of production loss for grazingmeat-breed lambs during Trichostrongylus colubriformis infection.Vet Parasitol2016 Jan 3026801591
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