Dexamethasone

Basic Info

Common NameDexamethasone(F06148)
2D Structure
FRCD IDF06148
CAS Number50-02-2
PubChem CID5743
FormulaC22H29FO5
IUPAC Name

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

InChI Key

UREBDLICKHMUKA-CXSFZGCWSA-N

InChI

InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1

Canonical SMILES

CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C

Isomeric SMILES

C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C

Synonyms
        
            Decadron
        
            Hexadecadrol
        
            dexamethasone
        
            50-02-2
        
            Dexamethazone
        
            Maxidex
        
            Decaspray
        
            Desametasone
        
            Dexacort
        
            Dexasone
Classifies
                

                  
                    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 - Pregnane-skeleton - 20-oxosteroid - 3-oxo-delta-1,4-steroid - 3-oxosteroid - 17-hydroxysteroid - 11-hydroxysteroid - 11-beta-hydroxysteroid - 9-halo-steroid - Halo-steroid - Oxosteroid - Delta-1,4-steroid - Alpha-hydroxy ketone - Cyclic alcohol - Tertiary alcohol - Ketone - Fluorohydrin - Halohydrin - Secondary alcohol - Cyclic ketone - Organooxygen compound - Alcohol - Primary alcohol - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Alkyl halide - Alkyl fluoride - Organohalogen compound - Organofluoride - 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 Weight392.467
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Complexity805
Monoisotopic Mass392.2
Exact Mass392.2
XLogP1.9
Formal Charge0
Heavy Atom Count28
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+0.9781
Human Intestinal AbsorptionHIA+0.9920
Caco-2 PermeabilityCaco2+0.8304
P-glycoprotein SubstrateSubstrate0.7862
P-glycoprotein InhibitorNon-inhibitor0.8112
Non-inhibitor0.8134
Renal Organic Cation TransporterNon-inhibitor0.7971
Distribution
Subcellular localizationMitochondria0.8255
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8733
CYP450 2D6 SubstrateNon-substrate0.9115
CYP450 3A4 SubstrateSubstrate0.7315
CYP450 1A2 InhibitorNon-inhibitor0.9380
CYP450 2C9 InhibitorNon-inhibitor0.9106
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9247
CYP450 3A4 InhibitorNon-inhibitor0.8308
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9169
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9558
Inhibitor0.5091
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.9399
Fish ToxicityHigh FHMT0.9926
Tetrahymena Pyriformis ToxicityHigh TPT0.9983
Honey Bee ToxicityHigh HBT0.7746
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.8328
Carcinogenicity (Three-class)Non-required0.7364
Model Value Unit
Absorption
Aqueous solubility-3.7026LogS
Caco-2 Permeability1.0834LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1482LD50, mol/kg
Fish Toxicity0.8318pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.0232pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HoneyJapan0. residue was detected
Other Aquatic AnimalJapan0. residue was detected
CrustaceansJapan0. residue was detected
Shelled MolluscasJapan0. residue was detected
Other FishJapan0. residue was detected
PerciformesJapan0. residue was detected
AnguilliformesJapan0. residue was detected
SalmoniformesJapan0. residue was detected
Other Poultry,EggsJapan0. residue was detected
Chicken,EggsJapan0. residue was detected
Other Poultry Animals,Edible OffalJapan0.01ppm
Chicken,Edible OffalJapan0.01ppm
Other Poultry Animals,KidneyJapan0.01ppm
Chicken,KidneyJapan0.01ppm
Chicken,LiverJapan0.01ppm
Other Poultry Animals,FatJapan0.01ppm
Chicken,FatJapan0.01ppm
Other Poultry Animals,MuscleJapan0.01ppm
Chicken,MuscleJapan0.01ppm
MilkJapan0.02ppm

References

TitleJournalDatePubmed ID
Antioxidant, anti-inflammatory, and enzyme inhibitory activity of natural plant flavonoids and their synthesized derivatives.J Biochem Mol Toxicol2018 Jan28972678
[Adverse reaction to food additives in a pediatric patient].Rev Alerg Mex2018 Apr-Jun29983016
Compound edaravone alleviates lipopolysaccharide (LPS)-induced acute lung injury in mice.Eur J Pharmacol2017 Sep 1528552343
Molecular Integration of Incretin and Glucocorticoid Action ReversesImmunometabolic Dysfunction and Obesity.Cell Metab2017 Oct 328943448
Opuntia humifusa modulates morphological changes characteristic of asthma viaIL-4 and IL-13 in an asthma murine model.Food Nutr Res2017 Oct 2429151835
FDA Drug Approval: Elotuzumab in Combination with Lenalidomide and Dexamethasone for the Treatment of Relapsed or Refractory Multiple Myeloma.Clin Cancer Res2017 Nov 1528249893
FDA Approval Summary: Daratumumab for Treatment of Multiple Myeloma After OnePrior Therapy.Oncologist2017 Nov28904172
In vitro and in silico assessment of the structure-dependent binding of bisphenol analogues to glucocorticoid receptor.Anal Bioanal Chem2017 Mar28078411
Long-Term Dexamethasone Exposure Down-Regulates Hepatic TFR1 and Reduces LiverIron Concentration in Rats.Nutrients2017 Jun 1728629118
Glucose homeostasis in rats treated with 4-vinylcyclohexene diepoxide is notworsened by dexamethasone treatment.J Steroid Biochem Mol Biol2017 Jan27264932
Proteasome inhibitors in AL amyloidosis: focus on mechanism of action and clinical activity.Hematol Oncol2017 Dec27647123
Co-administration of walnut (Juglans regia) prevents systemic hypertensioninduced by long-term use of dexamethasone: a promising strategy for steroidconsumers.Pharm Biol2017 Dec27653214
Upper and lower respiratory tract microbiota in horses: bacterial communitiesassociated with health and mild asthma (inflammatory airway disease) and effects of dexamethasone.BMC Microbiol2017 Aug 2328835202
Anti-inflammatory effects of physalin E from Physalis angulata on lipopolysaccharide-stimulated RAW 264.7 cells through inhibition of NF-κB pathway.Immunopharmacol Immunotoxicol2017 Apr28152630
Dietary 2-oxoglutarate prevents bone loss caused by neonatal treatment withmaximal dexamethasone dose.Exp Biol Med (Maywood)2017 Apr28178857
Dexamethasone-induced hepatomegaly and steatosis in larval zebrafish.J Toxicol Sci201728717104
Anti-inflammatory effects of Salvia plebeia R. Br extract in vitro and in ovalbumin-induced mouse model.Biol Res2016 Oct 527716424
Dexamethasone reverses the effects of high glucose on human retinal endothelialcell permeability and proliferation in vitro.Exp Eye Res2016 Oct27523466
Natural product HTP screening for antibacterial (E.coli 0157:H7) and anti-inflammatory agents in (LPS from E. coli O111:B4) activated macrophages and microglial cells; focus on sepsis.BMC Complement Altern Med2016 Nov 1527846826
Activation of inflammatory immune gene cascades by lipopolysaccharide (LPS) in the porcine colonic tissue ex-vivo model.Clin Exp Immunol2016 Nov27406528