Betamethasone (CED0002257)

Record Information
Version1.0
Creation Date2016-05-22 03:37:47 UTC
Update Date2026-05-14 16:38:58 UTC
Accession NumberCHEM016586
Identification
Common NameBetamethasone
ClassSmall Molecule
Description
Betamethasone is an organic compound with the formula C22H29FO5 and an average molecular weight of 392.46 g/mol. Betamethasone belongs to the hydroxysteroids, a subclass of steroids and steroid derivatives within the organic compounds. In terms of biological activity, it functions as an agonist of the Glucocorticoid receptor (NR3C1). The compound is found in or released from 13 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, these sources include corticosteroids, intestinal antiinflammatory agents, vasoprotectives, and corticosteroids in combination with antibiotics or antiseptics, among six others. Additionally, it is associated with electrical and electronic equipment, specifically amplifiers and antennas. Betamethasone is associated with a wide variety of recorded exposure routes. These include oral, rectal, and topical applications, as well as auricular, ophthalmic, and cutaneous routes. Injectable routes of exposure include intravenous, intravascular, intramuscular, intradermal, and intralesional administration. Specialized delivery methods include infiltration, intraspinal, intrathecal, epidural, perineural, intra-articular, intrabursal, and soft tissue administration.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
16beta-Methyl-1,4-pregnadiene-9alpha-fluoro-11beta,17alpha,21-triol-3,20-dioneChEBI
9-Fluoro-16beta-methylprednisoloneChEBI
9alpha-Fluoro-16beta-methylprednisoloneChEBI
beta-Methasone alcoholChEBI
BetadexamethasoneChEBI
BetametasonaChEBI
BetamethasonumChEBI
RinderonChEBI
CelestoneKegg
16b-Methyl-1,4-pregnadiene-9a-fluoro-11b,17a,21-triol-3,20-dioneGenerator
16Β-methyl-1,4-pregnadiene-9α-fluoro-11β,17α,21-triol-3,20-dioneGenerator
9-Fluoro-16b-methylprednisoloneGenerator
9-Fluoro-16β-methylprednisoloneGenerator
9a-Fluoro-16b-methylprednisoloneGenerator
9Α-fluoro-16β-methylprednisoloneGenerator
b-Methasone alcoholGenerator
Β-methasone alcoholGenerator
CelestonaHMDB
CelestonHMDB
CellestodermHMDB
FlubenisoloneHMDB
Chemical FormulaC22H29FO5
Average Molecular Mass392.461 g/mol
Monoisotopic Mass392.200 g/mol
CAS Registry Number378-44-9
IUPAC Name(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one
Traditional Namebetamethasone
SMILES[H][C@@]12C[C@H](C)[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
InChI IdentifierInChI=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
InChI KeyUREBDLICKHMUKA-DVTGEIKXSA-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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • Progestogin-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
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.05 g/LALOGPS
logP1.93ALOGPS
logP1.68ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.42ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity102.49 m³·mol⁻¹ChemAxon
Polarizability40.88 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-02ai-2923000000-e31987dc12e5a702a42eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-2414490000-490d5cc0ad1eca76d44eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-3960000000-a7dc9d06200fd3114dc2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0239000000-6da1b4bf9567b7486622Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05i4-2930000000-bc11f96b96bcca3051a8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dj-3960000000-a7dc9d06200fd3114dc2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aba-1910000000-8935fdec4e43c6b2520cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fs-0920000000-d3237d51f90b799cade8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0479000000-1ae6657fbbd9e214927dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00bj-0961000000-a979b7d63a7b4fe6d61cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00mo-4900000000-ed826eaa39e06794dd57Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0597-2900000000-c737db0736f32d648cdcNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-0479000000-9c467f1e2a15e843c7d4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00bj-0961000000-a31db5e71a2e0f790312Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00mo-4900000000-cc89b249ed3298324db9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0ab9-0139000000-b7e783cabe26054bda86Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05i4-2920000000-7776d2f083fad00b15b7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0597-2900000000-f6508c643ffd50a53419Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002f-0009000000-6926653590903a3ace6cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06vl-0019000000-301b3962f9291bee1ee9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0g4r-1294000000-8f3712f110452655373eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-a4ddb0d0eed36d96b76fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05uu-1009000000-badd4f30582cf375bbdfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-8019000000-2bad3a1904cfc0e5431fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-054o-0009000000-3702a20eae7c02129c8dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ec-0329000000-4bf118d6006bbe37897eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052r-3592000000-3398f331604edab7af4cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03e9-0009000000-8f2ff94364bde578948fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-c53af86e47eae3fd458cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kai-1009000000-350faaa7d5aecf256744Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
674.0Log mg/kg[380:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
258Intestinal antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
292VasoprotectivesHealthcare, pharmaceuticals & veterinary productsNot Available
309CorticosteroidsHealthcare, pharmaceuticals & veterinary productsNot Available
310Corticosteroids, combinations with antisepticsHealthcare, pharmaceuticals & veterinary productsNot Available
311Corticosteroids, combinations with antibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
389Nasal preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
391Drugs for obstructive airway diseasesHealthcare, pharmaceuticals & veterinary productsNot Available
396Antiinflammatory agentsHealthcare, pharmaceuticals & veterinary productsNot Available
397Antiinflammatory agents and antiinfectives in combinationHealthcare, pharmaceuticals & veterinary productsNot Available
406OtologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
407Ophthalmological and otological preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Glucocorticoid receptor structureClick to view 3D structureGlucocorticoid receptorP04150HumansPredicted (SEA)0.0778492
Click to view 3D structureTyrosine aminotransferaseP04694Rattus norvegicusPredicted (SEA)0.155698
Progesterone receptor structureClick to view 3D structureProgesterone receptorP06401HumansPredicted (SEA)0.389246
Click to view 3D structureProgesterone receptorQ690N0Bos taurusPredicted (SEA)0.155698
Click to view 3D structureGlucocorticoid receptorP06536Rattus norvegicusPredicted (SEA)0.467095
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)7.00643
Pyruvate carboxylase, mitochondrial structureClick to view 3D structurePyruvate carboxylase, mitochondrialP11498HumansPredicted (SEA)0.0778492
Click to view 3D structureNuclear receptor subfamily 1 group I member 2Q9R1A7Rattus norvegicusPredicted (SEA)0.0778492
Mineralocorticoid receptor structureClick to view 3D structureMineralocorticoid receptorP08235HumansPredicted (SEA)2.02408
Click to view 3D structureAndrogen receptorP15207Rattus norvegicusPredicted (SEA)5.91654
Androgen receptor structureClick to view 3D structureAndrogen receptorP10275HumansPredicted (SEA)14.48
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)3.73676
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansPredicted (SEA)40.8708
Phospholipase A2, membrane associated structureClick to view 3D structurePhospholipase A2, membrane associatedP14555HumansPredicted (SEA)5.0602
Protein kinase C delta type structureClick to view 3D structureProtein kinase C delta typeQ05655HumansPredicted (SEA)322.451
Protein kinase C eta type structureClick to view 3D structureProtein kinase C eta typeP24723HumansPredicted (SEA)66.3275
Protein kinase C epsilon type structureClick to view 3D structureProtein kinase C epsilon typeQ02156HumansPredicted (SEA)91.3171
Protein kinase C alpha type structureClick to view 3D structureProtein kinase C alpha typeP17252HumansPredicted (SEA)82.1309
Estrogen receptor beta structureClick to view 3D structureEstrogen receptor betaQ92731HumansPredicted (SEA)53.7938
Corticosteroid-binding globulin structureClick to view 3D structureCorticosteroid-binding globulinP08185HumansPredicted (SEA)15.8812
Inhibitor of nuclear factor kappa-B kinase subunit beta structureClick to view 3D structureInhibitor of nuclear factor kappa-B kinase subunit betaO14920HumansPredicted (SEA)240.243
RAC-alpha serine/threonine-protein kinase structureClick to view 3D structureRAC-alpha serine/threonine-protein kinaseP31749HumansPredicted (SEA)530.542
cAMP-dependent protein kinase catalytic subunit alpha structureClick to view 3D structurecAMP-dependent protein kinase catalytic subunit alphaP17612HumansPredicted (SEA)513.571
Rho-associated protein kinase 2 structureClick to view 3D structureRho-associated protein kinase 2O75116HumansPredicted (SEA)586.36
Rho-associated protein kinase 1 structureClick to view 3D structureRho-associated protein kinase 1Q13464HumansPredicted (SEA)591.576
Concentrations
Not Available
External Links
DrugBank IDDB00443
HMDB IDHMDB0014586
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBetamethasone
Chemspider ID9399
ChEBI ID3077
PubChem Compound ID9782
Kegg Compound IDC06848
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. The lipid handbook with CD-ROM