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Dexamethasone (CHEM003936)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (7)XML
Record Information
Version1.0
Creation Date2014-10-14 21:18:42 UTC
Update Date2016-10-28 10:04:08 UTC
Accession NumberCHEM003936
Identification
Common NameDexamethasone
ClassSmall Molecule
DescriptionAn anti-inflammatory 9-fluoro-glucocorticoid. [PubChem]
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds - Waste Water
  • Suspected Compounds – Schymanski Project
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Anti-Inflammatory Agent
  • Antiemetic
  • Antineoplastic Agent, Hormonal
  • Drug
  • Glucocorticoid
  • Metabolite
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Dehydro-16alpha-methyl-9alpha-fluorohydrocortisoneChEBI
16alpha-Methyl-9alpha-fluoro-1-dehydrocortisolChEBI
9alpha-Fluoro-16alpha-methylprednisoloneChEBI
DecadronChEBI
DexametasonaChEBI
DexamethasonumChEBI
MaxidexKegg
1-Dehydro-16a-methyl-9a-fluorohydrocortisoneGenerator
1-Dehydro-16α-methyl-9α-fluorohydrocortisoneGenerator
16a-Methyl-9a-fluoro-1-dehydrocortisolGenerator
16Α-methyl-9α-fluoro-1-dehydrocortisolGenerator
9a-Fluoro-16a-methylprednisoloneGenerator
9Α-fluoro-16α-methylprednisoloneGenerator
1-Dehydro-16alpha -methyl-9alpha -fluorohydrocortisoneHMDB
16-alpha-Methyl-9-alpha-fluoro-1-dehydrocortisolHMDB
16-alpha-Methyl-9-alpha-fluoro-delta1-hydrocortisoneHMDB
16-alpha-Methyl-9-alpha-fluoroprednisoloneHMDB
16alpha -Methyl-9alpha -fluoro-1-dehydrocortisolHMDB
16alpha -Methyl-9alpha -fluoroprednisoloneHMDB
16alpha-Methyl-9alpha-fluoroprednisoloneHMDB
9-alpha-Fluoro-16-alpha-methylprednisoloneHMDB
9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dioneHMDB
9-Fluoro-11alpha -methylpregna-1,4-diene-3,20-dioneHMDB
9-Fluoro-16-methylprednisoloneHMDB
9a-Fluoro-16BETA-methylprednisoloneHMDB
9alpha -Fluoro-16alpha -methylprednisoloneHMDB
9alpha-Fluoro-16alpha-methyl-prednisoloneHMDB
Aeroseb-DHMDB
Aeroseb-dexHMDB
Ak dex OPH otic soln 0.1%HMDB
alpha -Fluoro-16-alpha -methylcortisolHMDB
AnaflogisticoHMDB
AphtasolonHMDB
Apo-dexamethasoneHMDB
AuxironHMDB
Azimycin (veterinary)HMDB
AziumHMDB
Azium (veterinary)HMDB
Bisu DSHMDB
CalonatHMDB
CorsonHMDB
CorsoneHMDB
CortisummanHMDB
DecacortinHMDB
DecadermHMDB
DecagelHMDB
DecalixHMDB
DecasoneHMDB
DecasprayHMDB
DectancylHMDB
DekacortHMDB
Delta1-9alpha-Fluoro-16alpha-methylcortisolHMDB
DeltafluoreneHMDB
DergraminHMDB
DesadreneHMDB
DesametasoneHMDB
DesamethasoneHMDB
DesametonHMDB
DeseronilHMDB
DEXHMDB
Dex-ideHMDB
DEXAHMDB
Dexa mamalletHMDB
Dexa-cortideltHMDB
Dexa-cortisylHMDB
Dexa-scherosonHMDB
Dexa-sineHMDB
DexacidinHMDB
DexacortHMDB
DexacortalHMDB
DexacortinHMDB
DexadeltoneHMDB
DexafarmaHMDB
DexalonaHMDB
DexametasoneHMDB
DexamethHMDB
DexamethansoneHMDB
Dexamethasone acetateHMDB
Dexamethasone alcoholHMDB
Dexamethasone baseHMDB
Dexamethasone intensolHMDB
Dexamethasone sodium phosphateHMDB
Dexamethasone-omegaHMDB
DexamethazoneHMDB
DexapolcortHMDB
DexaposHMDB
DexaprolHMDB
DexasonHMDB
DexasoneHMDB
Dexasone 0.5MGHMDB
Dexasone 0.75MGHMDB
Dexasone 4MGHMDB
DexasporinHMDB
DexinolonHMDB
DexinoralHMDB
DexoneHMDB
DEXONE 0.5HMDB
DEXONE 0.75HMDB
DEXONE 1.5HMDB
DEXONE 4HMDB
DextelanHMDB
DezoneHMDB
DinormonHMDB
DXMHMDB
DXMSHMDB
FluormethylprednisoloneHMDB
FortecortinHMDB
GammacortenHMDB
HexadecadrolHMDB
HexadrolHMDB
Hexadrol elixirHMDB
HL-DexHMDB
Isopto-dexHMDB
Lokalison FHMDB
LoverineHMDB
LuxazoneHMDB
Maxidex ont 0.1%HMDB
Maxidex sus 0.1%HMDB
MaxitrolHMDB
MediamethasoneHMDB
MethylfluorprednisoloneHMDB
MexidexHMDB
MymethasoneHMDB
Naquasone (veterinary)HMDB
Neomycin and polymyxin b sulfates and dexamethasoneHMDB
Neomycin and polymyxin b sulphates and dexamethasoneHMDB
NSC 34521HMDB
Ocu-trolHMDB
OradexonHMDB
Pet derm IIIHMDB
PHL-DexamethasoneHMDB
PMS Dexamethasone elixir 0.5mg/5MLHMDB
PMS-DexamethasoneHMDB
PolicortHMDB
Prednisolon FHMDB
Prednisolone FHMDB
ProdexHMDB
Sandoz dexamethasoneHMDB
SK-DexamethasoneHMDB
SpolovenHMDB
Sunia sol DHMDB
SuperprednolHMDB
TobradexHMDB
Tobramycin and dexamethasoneHMDB
Tresaderm (veterinary)HMDB
TurbinaireHMDB
VisumetazoneHMDB
MillicortenHMDB
Decaject-l.a.HMDB
DecamethHMDB
DexpakHMDB
Foy brand OF dexamethasoneHMDB
Merz brand 1 OF dexamethasoneHMDB
Merz brand 2 OF dexamethasoneHMDB
ICN brand OF dexamethasoneHMDB
Alcon brand OF dexamethasoneHMDB
DecajectHMDB
Decaject l.a.HMDB
ECR brand OF dexamethasoneHMDB
Merck brand OF dexamethasoneHMDB
Chemical FormulaC22H29FO5
Average Molecular Mass392.461 g/mol
Monoisotopic Mass392.200 g/mol
CAS Registry Number50-02-2
IUPAC Name(1R,2S,10S,11S,13R,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 Namedexamethasone
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+/m1/s1
InChI KeyUREBDLICKHMUKA-CXSFZGCWSA-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
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceNot Available
Experimental Properties
PropertyValue
Melting Point170-229 °C
Boiling PointNot Available
Solubility89 mg/L (at 25 °C)
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
Polarizability40.83 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-02ai-2923000000-e31987dc12e5a702a42eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS)splash10-0006-2414490000-490d5cc0ad1eca76d44eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4r-0696000000-1df7921eb1369fef69c4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00dj-3960000000-e9ee044790c0655981b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01ot-0904000000-dbbc479b104fbe981ce7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0903000000-c84b561c97b1277fed56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0903000000-b498846e21073040b905View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-b04e175289861dc518f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0900000000-b04e175289861dc518f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-01ot-0904000000-dbbc479b104fbe981ce7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0903000000-c84b561c97b1277fed56View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0002-0903000000-b498846e21073040b905View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006w-0719000000-d4feef3f83ca022aa94dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0913000000-3c8e5afb526637f1e822View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0910000000-57f268bed9b190ee6066View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-cfdda545a27ec16c8b76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-c70817ad99741f01b675View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0009000000-ecbabc9fe90444b14afeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fr-0019000000-4161bdd8f3deed25b9bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-002r-0594000000-bf4495b7906d53ad019dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00ds-0980000000-c4e88ec70fa28252f6f7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0009000000-6926653590903a3ace6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vl-0019000000-301b3962f9291bee1ee9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0g4r-1294000000-8f3712f110452655373eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-a4ddb0d0eed36d96b76fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05uu-1009000000-badd4f30582cf375bbdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8019000000-2bad3a1904cfc0e5431fView in MoNA
Toxicity Profile
Route of Exposure80-90%
Mechanism of ToxicityDexamethasone is a glucocorticoid agonist. Unbound dexamethasone crosses cell membranes and binds with high affinity to specific cytoplasmic glucocorticoid receptors. This complex binds to DNA elements (glucocorticoid response elements) which results in a modification of transcription and, hence, protein synthesis in order to achieve inhibition of leukocyte infiltration at the site of inflammation, interference in the function of mediators of inflammatory response, suppression of humoral immune responses, and reduction in edema or scar tissue. The antiinflammatory actions of dexamethasone are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.
MetabolismHepatic.
Toxicity ValuesOral, rat LD50: >3 gm/kg. Signs of overdose include retinal toxicity, glaucoma, subcapsular cataract, gastrointestinal bleeding, pancreatitis, aseptic bone necrosis, osteoporosis, myopathies, obesity, edemas, hypertension, proteinuria, diabetes, sleep disturbances, psychiatric syndromes, delayed wound healing, atrophy and fragility of the skin, ecchymosis, and pseudotumor cerebri.
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesInjection: for the treatment of endocrine disorders, rheumatic D=disorders, collagen diseases, dermatologic diseases, allergic statesc, ophthalmic diseases, gastrointestinal diseases, respiratory diseases, hematologic disorders, neoplastic diseases, edematous states, cerebral edema.
Ophthalmic ointment and solution: for the treatment of steroid responsive inflammatory conditions of the palpebral and bulbar conjunctiva, cornea, and anterior segment of the globe.
Ophthalmic solution only: for the treatment of steroid responsive inflammatory conditions of the external auditory meatus
Topic cream: for relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses
Oral aerosol: for the treatment of bronchial asthma and related corticosteroid responsive bronchospastic states intractable to adequate trial of conventional therapy
Intranasal aerosol: for the treatment of allergic ot inflammatory nasal conditions, and nasal polyps
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
StatusValueUnitSample LocationReference
DrugBank IDDB01234
HMDB IDHMDB0015364
FooDB IDFDB001355
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDexamethasone
Chemspider ID5541
ChEBI ID41879
PubChem Compound ID5743
Kegg Compound IDC15643
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Fried, J.; US. Patent 2,852.51 1; September 16, 1958; assigned to Olin Mathieson Chemical Corporation.
Muller, G., Bardoneschi, R. and Jolly, J.; U.S. Patent 3,007,923; November 7, 1961; assigned to Les Laboratories Francais de Chimiotherapie, France.

MSDSNot Available
General References
1. Bisgaard T: Analgesic treatment after laparoscopic cholecystectomy: a critical assessment of the evidence. Anesthesiology. 2006 Apr;104(4):835-46.
2. Chisti MJ, Bardhan PK, Huq S, Khan WA, Khan AM, Sharifuzzaman, Salam MA: High-dose intravenous dexamethasone in the management of diarrheal patients with enteric fever and encephalopathy. Southeast Asian J Trop Med Public Health. 2009 Sep;40(5):1065-73.
3. Ross DD, Alexander CS: Management of common symptoms in terminally ill patients: Part I. Fatigue, anorexia, cachexia, nausea and vomiting. Am Fam Physician. 2001 Sep 1;64(5):807-14.
4. Belanto JJ, Diaz-Perez SV, Magyar CE, Maxwell MM, Yilmaz Y, Topp K, Boso G, Jamieson CH, Cacalano NA, Jamieson CA: Dexamethasone induces dysferlin in myoblasts and enhances their myogenic differentiation. Neuromuscul Disord. 2010 Feb;20(2):111-21. doi: 10.1016/j.nmd.2009.12.003. Epub 2010 Jan 18.
5. Liu JZ, Huang YH, Hand PJ: Effects of dexamethasone on electroacupuncture analgesia and central nervous system metabolism. Acupunct Electrother Res. 1988;13(1):9-23.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. 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.
8. 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.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
11. The lipid handbook with CD-ROM
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=11508649
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=18272184
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18524938