Record Information
Version1.0
Creation date2010-04-08 22:04:56 UTC
Update date2018-05-28 23:05:47 UTC
Primary IDFDB001355
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDexamethasone
DescriptionGlucocorticoid with potent antiinflammatory props. Not FDA approved for use in food-producing animals, but may be used illegally Dexamethasone and its derivatives, dexamethasone sodium phosphate and dexamethasone acetate, are synthetic glucocorticoids. It is used for its antiinflammatory or immunosuppressive properties and ability to penetrate the CNS, dexamethasone is used alone to manage cerebral edema and with tobramycin to treat corticosteroid-responsive inflammatory ocular conditions.; Dexamethasone can be used in the context of congenital adrenal hyperplasia, to prevent virilisation of a female fetus. If one or both parents are carriers of mutations to the CYP21 (CYP21A2) gene, the mother may start dexamethasone treatment within 7 weeks of conception. At the 12th week, a chorionic villus sample will determine whether the fetus is male (in which case the dexamethasone is stopped) or female. Subsequent DNA analysis can then reveal whether the female fetus is a carrier of the mutation, in which case dexamethasone treatment must continue until birth. The side-effects for the mother can be severe and the long-term impact on the child is not clear.; Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid hormones. It acts as an anti-inflammatory and immunosuppressant. Its potency is about 20-30 times that of hydrocortisone and 4-5 times of prednisone.
CAS Number50-02-2
Structure
Thumb
Synonyms
SynonymSource
α-Fluoro-16-α-methylcortisolbiospider
α-fluoro-16α-methyl-biospider
1-Dehydro-16α-methyl-9α-fluorohydrocortisonebiospider
1-dehydro-16a-Methyl-9a-fluorohydrocortisoneGenerator
1-dehydro-16alpha -Methyl-9alpha -fluorohydrocortisoneHMDB
1-Dehydro-16alpha-methyl-9alpha-fluorohydrocortisonebiospider
1-dehydro-16α-methyl-9α-fluorohydrocortisoneGenerator
16-alpha-Methyl-9-alpha-fluoro-1-dehydrocortisolbiospider
16-alpha-Methyl-9-alpha-fluoro-delta(sup 1)-hydrocortisonebiospider
16-alpha-Methyl-9-alpha-fluoro-delta1-hydrocortisonebiospider
16-alpha-Methyl-9-alpha-fluoroprednisolonebiospider
16α-Methyl-9α-fluoro-1-dehydrocortisolbiospider
16α-Methyl-9α-fluoroprednisolonebiospider
16a-Methyl-9a-fluoro-1-dehydrocortisolGenerator
16alpha -Methyl-9alpha -fluoro-1-dehydrocortisolHMDB
16alpha -Methyl-9alpha -fluoroprednisoloneHMDB
16alpha-Methyl-9alpha-fluoro-1-dehydrocortisolbiospider
16alpha-Methyl-9alpha-fluoro-delta(sup 1)-hydrocortisonebiospider
16alpha-Methyl-9alpha-fluoroprednisolonebiospider
16α-methyl-9α-fluoro-1-dehydrocortisolGenerator
9-alpha-Fluoro-16-alpha-methylprednisolonebiospider
9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dionedb_source
9-Fluoro-11α-methylpregna-1,4-diene-3,20-dionebiospider
9-Fluoro-11alpha -methylpregna-1,4-diene-3,20-dioneHMDB
9-Fluoro-16-methylprednisolonedb_source
9α-Fluoro-16α-methylprednisolonebiospider
9a-Fluoro-16a-methylprednisoloneGenerator
9A-FLUORO-16BETA-METHYLPREDNISOLONEbiospider
9alpha -Fluoro-16alpha -methylprednisoloneHMDB
9alpha-Fluoro-16alpha-methyl-prednisoloneHMDB
9alpha-Fluoro-16alpha-methylprednisolonebiospider
9α-fluoro-16α-methylprednisoloneGenerator
Aeroseb-dbiospider
Aeroseb-dexbiospider
Ak Dex Oph Otic Soln 0.1%biospider
alpha -Fluoro-16-alpha -methylcortisolHMDB
Anaflogisticobiospider
Aphtasolonbiospider
Apo-dexamethasonebiospider
Auxironbiospider
Azimycin (veterinary)biospider
Aziumbiospider
Azium (veterinary)biospider
Bisu DSbiospider
Calonatbiospider
Corsonbiospider
Corsonebiospider
Cortisummanbiospider
Decacortinbiospider
Decadermdb_source
Decadronbiospider
Decagelbiospider
Decalixbiospider
Decasonebiospider
Decaspraybiospider
Dectancylbiospider
Dekacortbiospider
delta(sup 1)-9-alpha-Fluoro-16-alpha-methylcortisolbiospider
delta1-9alpha-Fluoro-16alpha-methylcortisolbiospider
Deltafluorenedb_source
Dergraminbiospider
Deronilbiospider
Desadrenebiospider
Desametasonedb_source
Desametasone [dcit]biospider
Desamethasonebiospider
Desametonbiospider
Deseronilbiospider
DEXbiospider
Dex-idebiospider
DEXAbiospider
Dexa mamalletbiospider
Dexa-cortideltbiospider
Dexa-cortisylbiospider
Dexa-scherosonbiospider
Dexa-sinebiospider
Dexacidinbiospider
Dexacortbiospider
Dexacortalbiospider
Dexacortinbiospider
Dexadeltonedb_source
Dexafarmabiospider
Dexalonabiospider
DexametasonaChEBI
Dexametasonedb_source
Dexamethbiospider
Dexamethansonebiospider
Dexamethasone (from sample)biospider
Dexamethasone [inn:ban:jan]biospider
Dexamethasone acetatebiospider
Dexamethasone alcoholbiospider
Dexamethasone basebiospider
Dexamethasone intensolbiospider
Dexamethasone sodium ateHMDB
Dexamethasone sodium phosphatebiospider
Dexamethasone-omegabiospider
Dexamethasonumbiospider
Dexamethazonedb_source
Dexapolcortbiospider
Dexaposbiospider
Dexaprolbiospider
Dexasonbiospider
Dexasonebiospider
Dexasone 0.5mgbiospider
Dexasone 0.75mgbiospider
Dexasone 4mgbiospider
Dexasporinbiospider
Dexinolonbiospider
Dexinoralbiospider
Dexonebiospider
DEXONE 0.5biospider
DEXONE 0.75biospider
DEXONE 1.5biospider
DEXONE 4biospider
Dextelanbiospider
Dezonebiospider
Dinormonbiospider
DXMbiospider
DXMSbiospider
FluormethylprednisoloneHMDB
Fortecortinbiospider
Gammacortenbiospider
Hexadecadroldb_source
Hexadroldb_source
Hexadrol elixirbiospider
HL-dexbiospider
Isopto-dexbiospider
Lokalison fbiospider
Loverinebiospider
Luxazonebiospider
Maxidexbiospider
Maxidex Ont 0.1%biospider
Maxidex Sus 0.1%biospider
Maxitrolbiospider
Mediamethasonebiospider
Methylfluorprednisolonebiospider
Mexidexbiospider
Millicortendb_source
MK 125db_source
Mymethasonebiospider
Naquasone (veterinary)biospider
Neomycin and polymyxin b sulfates and dexamethasonebiospider
Neomycin and polymyxin b sulphates and dexamethasoneHMDB
NSC 34521db_source
Ocu-trolbiospider
Oradexonbiospider
Pet derm IIIbiospider
PHL-dexamethasonebiospider
Pms Dexamethasone Elixir 0.5mg/5mlbiospider
PMS-dexamethasonebiospider
Policortbiospider
Prednisolon fbiospider
Prednisolone fbiospider
Prednisolone, 9α-fluoro-16α-methyl-biospider
Prednisolone, 9alpha-fluoro-16alpha-methyl-biospider
Pregna-1,4-diene-3,20-dione, 9-fluoro-11α-methyl-biospider
Prodexbiospider
Sandoz dexamethasonebiospider
SK-dexamethasonebiospider
Spolovenbiospider
Sunia sol dbiospider
Superprednoldb_source
Tobradexbiospider
Tobramycin and dexamethasonebiospider
Tresaderm (veterinary)biospider
Turbinairebiospider
Visumetazonebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.051 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
Polarizability41 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC22H29FO5
IUPAC name1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
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
InChI KeyUREBDLICKHMUKA-UHFFFAOYSA-N
Isomeric SMILESCC1CC2C3CCC4=CC(=O)C=CC4(C)C3(F)C(O)CC2(C)C1(O)C(=O)CO
Average Molecular Weight392.4611
Monoisotopic Molecular Weight392.199902243
Classification
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
  • 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
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 67.33%; H 7.45%; F 4.84%; O 20.38%DFC
Melting PointMp 262-264°DFC
Boiling PointNot Available
Experimental Water Solubility0.089 mg/mL at 25 oCYALKOWSKY,SH & HE,Y (2003)
Experimental logP1.83HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]25D +77.5 (dioxan)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID5541
ChEMBL IDCHEMBL384467
KEGG Compound IDC15643
Pubchem Compound ID5743
Pubchem Substance IDNot Available
ChEBI ID41879
Phenol-Explorer IDNot Available
DrugBank IDDB01234
HMDB IDHMDB15364
CRC / DFC (Dictionary of Food Compounds) IDBZQ30-M:BZQ30-M
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDEX
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDexamethasone
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Nuclear receptor subfamily 0 group B member 1NR0B1P51843
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference