Betamethasone

Basic Info

Common NameBetamethasone(F05691)
2D Structure
FRCD IDF05691
CAS Number378-44-9
PubChem CID9782
FormulaC22H29FO5
IUPAC Name

(8S,9R,10S,11S,13S,14S,16S,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-DVTGEIKXSA-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-/m0/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
        
            betamethasone
        
            378-44-9
        
            Betadexamethasone
        
            Flubenisolone
        
            Celestone
        
            Betamethazone
        
            Rinderon
        
            Betacorlan
        
            Betacortril
        
            Betamamallet
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 - 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
HoneyJapan0.0003ppm
Other Aquatic AnimalJapan0.0003ppm
CrustaceansJapan0.0003ppm
Shelled MolluscasJapan0.0003ppm
Other FishJapan0.0003ppm
PerciformesJapan0.0003ppm
AnguilliformesJapan0.0003ppm
SalmoniformesJapan0.0003ppm
Other Poultry,EggsJapan0.0003ppm
Chicken,EggsJapan0.0003ppm
Other Poultry Animals,Edible OffalJapan0.0003ppm
Chicken,Edible OffalJapan0.0003ppm
Other Poultry Animals,KidneyJapan0.0003ppm
Chicken,KidneyJapan0.0003ppm
Other Poultry Animals,LiverJapan0.0003ppm
Chicken,LiverJapan0.0003ppm
Other Poultry Animals,FatJapan0.0003ppm
Chicken,FatJapan0.0003ppm
Other Poultry Animals,MuscleJapan0.0003ppm
Chicken,MuscleJapan0.0003ppm

References

TitleJournalDatePubmed ID
Effect-based detection of synthetic glucocorticoids in bovine urine.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201525569131
Fast and multiresidue determination of twenty glucocorticoids in bovine milkusing ultra high performance liquid chromatography-tandem mass spectrometry.J Chromatogr A2013 Jun 1423643098
Detection and quantitative analysis of 21 veterinary drugs in river water usinghigh-pressure liquid chromatography coupled to tandem mass spectrometry.Environ Sci Pollut Res Int2012 Sep22392691
Validation of a multi-residue enzyme-linked immunosorbent assay for qualitativescreening of corticosteroids in liver, urine and milk.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2011Sep21905839
Development of a liquid chromatography-tandem mass spectrometry with pressurized liquid extraction for determination of glucocorticoid residues in edible tissues.J Chromatogr B Analyt Technol Biomed Life Sci2011 Jan 1521195680
Recombinant cell bioassays for the detection of (gluco)corticosteroids andendocrine-disrupting potencies of several environmental PCB contaminants.Anal Bioanal Chem2011 Aug21681646
Development of a liquid chromatography-tandem mass spectrometry (LC-MS/MS) methodfor the quantification of glucocorticoid residues in edible tissues of swine,cattle, sheep, and chicken.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2010Oct20658401
Cluster headache.BMJ Clin Evid2010 Feb 921718584
Disrupted secretory activation of the mammary gland after antenatalglucocorticoid treatment in sheep.Reproduction2008 Nov18663017
Effect of preterm birth and antenatal corticosteroid treatment on lactogenesis IIin women.Pediatrics2008 Jan18166549
Cluster headache.BMJ Clin Evid2008 Feb 1519450329
Vitamins C and E in the latency period in women with preterm premature rupture ofmembranes.Int J Gynaecol Obstet2005 Jul15907848
Chemiluminescence detection of nine corticosteroids in liver.Analyst2000 Nov11193094
Effects of Kakkon-to and Sairei-to on experimental elevation of aqueous flare in pigmented rabbits.Jpn J Ophthalmol1999 Jul-Aug10482472
Assessment of the welfare of food restricted male broiler breeder poultry withmusculoskeletal disease.Res Vet Sci1994 Jul7973090
[Studies of toxicity of hydrocortisone 17-butyrate 21-propionate -5. Chronic toxicity in rats by percutaneous administration (author's transl)].J Toxicol Sci1981 Jul7310935