ContaminantDB: Dexamethasone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2014-10-14 21:18:42 UTC

Update Date

2026-03-26 18:28:25 UTC

Accession Number

CHEM003936

Identification

Common Name

Dexamethasone

Class

Small Molecule

Description

An 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Dehydro-16alpha-methyl-9alpha-fluorohydrocortisone	ChEBI
16alpha-Methyl-9alpha-fluoro-1-dehydrocortisol	ChEBI
9alpha-Fluoro-16alpha-methylprednisolone	ChEBI
Decadron	ChEBI
Dexametasona	ChEBI
Dexamethasonum	ChEBI
Maxidex	Kegg
1-Dehydro-16a-methyl-9a-fluorohydrocortisone	Generator
1-Dehydro-16α-methyl-9α-fluorohydrocortisone	Generator
16a-Methyl-9a-fluoro-1-dehydrocortisol	Generator
16Α-methyl-9α-fluoro-1-dehydrocortisol	Generator
9a-Fluoro-16a-methylprednisolone	Generator
9Α-fluoro-16α-methylprednisolone	Generator
1-Dehydro-16alpha -methyl-9alpha -fluorohydrocortisone	HMDB
16-alpha-Methyl-9-alpha-fluoro-1-dehydrocortisol	HMDB
16-alpha-Methyl-9-alpha-fluoro-delta1-hydrocortisone	HMDB
16-alpha-Methyl-9-alpha-fluoroprednisolone	HMDB
16alpha -Methyl-9alpha -fluoro-1-dehydrocortisol	HMDB
16alpha -Methyl-9alpha -fluoroprednisolone	HMDB
16alpha-Methyl-9alpha-fluoroprednisolone	HMDB
9-alpha-Fluoro-16-alpha-methylprednisolone	HMDB
9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione	HMDB
9-Fluoro-11alpha -methylpregna-1,4-diene-3,20-dione	HMDB
9-Fluoro-16-methylprednisolone	HMDB
9a-Fluoro-16BETA-methylprednisolone	HMDB
9alpha -Fluoro-16alpha -methylprednisolone	HMDB
9alpha-Fluoro-16alpha-methyl-prednisolone	HMDB
Aeroseb-D	HMDB
Aeroseb-dex	HMDB
Ak dex OPH otic soln 0.1%	HMDB
alpha -Fluoro-16-alpha -methylcortisol	HMDB
Anaflogistico	HMDB
Aphtasolon	HMDB
Apo-dexamethasone	HMDB
Auxiron	HMDB
Azimycin (veterinary)	HMDB
Azium	HMDB
Azium (veterinary)	HMDB
Bisu DS	HMDB
Calonat	HMDB
Corson	HMDB
Corsone	HMDB
Cortisumman	HMDB
Decacortin	HMDB
Decaderm	HMDB
Decagel	HMDB
Decalix	HMDB
Decasone	HMDB
Decaspray	HMDB
Dectancyl	HMDB
Dekacort	HMDB
Delta1-9alpha-Fluoro-16alpha-methylcortisol	HMDB
Deltafluorene	HMDB
Dergramin	HMDB
Desadrene	HMDB
Desametasone	HMDB
Desamethasone	HMDB
Desameton	HMDB
Deseronil	HMDB
DEX	HMDB
Dex-ide	HMDB
DEXA	HMDB
Dexa mamallet	HMDB
Dexa-cortidelt	HMDB
Dexa-cortisyl	HMDB
Dexa-scheroson	HMDB
Dexa-sine	HMDB
Dexacidin	HMDB
Dexacort	HMDB
Dexacortal	HMDB
Dexacortin	HMDB
Dexadeltone	HMDB
Dexafarma	HMDB
Dexalona	HMDB
Dexametasone	HMDB
Dexameth	HMDB
Dexamethansone	HMDB
Dexamethasone acetate	HMDB
Dexamethasone alcohol	HMDB
Dexamethasone base	HMDB
Dexamethasone intensol	HMDB
Dexamethasone sodium phosphate	HMDB
Dexamethasone-omega	HMDB
Dexamethazone	HMDB
Dexapolcort	HMDB
Dexapos	HMDB
Dexaprol	HMDB
Dexason	HMDB
Dexasone	HMDB
Dexasone 0.5MG	HMDB
Dexasone 0.75MG	HMDB
Dexasone 4MG	HMDB
Dexasporin	HMDB
Dexinolon	HMDB
Dexinoral	HMDB
Dexone	HMDB
DEXONE 0.5	HMDB
DEXONE 0.75	HMDB
DEXONE 1.5	HMDB
DEXONE 4	HMDB
Dextelan	HMDB
Dezone	HMDB
Dinormon	HMDB
DXM	HMDB
DXMS	HMDB
Fluormethylprednisolone	HMDB
Fortecortin	HMDB
Gammacorten	HMDB
Hexadecadrol	HMDB
Hexadrol	HMDB
Hexadrol elixir	HMDB
HL-Dex	HMDB
Isopto-dex	HMDB
Lokalison F	HMDB
Loverine	HMDB
Luxazone	HMDB
Maxidex ont 0.1%	HMDB
Maxidex sus 0.1%	HMDB
Maxitrol	HMDB
Mediamethasone	HMDB
Methylfluorprednisolone	HMDB
Mexidex	HMDB
Mymethasone	HMDB
Naquasone (veterinary)	HMDB
Neomycin and polymyxin b sulfates and dexamethasone	HMDB
Neomycin and polymyxin b sulphates and dexamethasone	HMDB
NSC 34521	HMDB
Ocu-trol	HMDB
Oradexon	HMDB
Pet derm III	HMDB
PHL-Dexamethasone	HMDB
PMS Dexamethasone elixir 0.5mg/5ML	HMDB
PMS-Dexamethasone	HMDB
Policort	HMDB
Prednisolon F	HMDB
Prednisolone F	HMDB
Prodex	HMDB
Sandoz dexamethasone	HMDB
SK-Dexamethasone	HMDB
Spoloven	HMDB
Sunia sol D	HMDB
Superprednol	HMDB
Tobradex	HMDB
Tobramycin and dexamethasone	HMDB
Tresaderm (veterinary)	HMDB
Turbinaire	HMDB
Visumetazone	HMDB
Millicorten	HMDB
Decaject-l.a.	HMDB
Decameth	HMDB
Dexpak	HMDB
Foy brand OF dexamethasone	HMDB
Merz brand 1 OF dexamethasone	HMDB
Merz brand 2 OF dexamethasone	HMDB
ICN brand OF dexamethasone	HMDB
Alcon brand OF dexamethasone	HMDB
Decaject	HMDB
Decaject l.a.	HMDB
ECR brand OF dexamethasone	HMDB
Merck brand OF dexamethasone	HMDB

Chemical Formula

C₂₂H₂₉FO₅

Average Molecular Mass

392.461 g/mol

Monoisotopic Mass

392.200 g/mol

CAS Registry Number

50-02-2

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 Name

dexamethasone

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 Identifier

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

InChI Key

UREBDLICKHMUKA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

21-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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

11beta-hydroxy steroid (CHEBI:41879 )
17alpha-hydroxy steroid (CHEBI:41879 )
glucocorticoid (CHEBI:41879 )
20-oxo steroid (CHEBI:41879 )
fluorinated steroid (CHEBI:41879 )
3-oxo-Delta(1),Delta(4)-steroid (CHEBI:41879 )
21-hydroxy steroid (CHEBI:41879 )
Pregnane and derivatives [Fig] (C15643 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	170-229 °C
Boiling Point	Not Available
Solubility	89 mg/L (at 25 °C)

Predicted Properties

Property	Value	Source
Water Solubility	0.05 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.68	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.42	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.49 m³·mol⁻¹	ChemAxon
Polarizability	40.83 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ai-2923000000-e31987dc12e5a702a42e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0006-2414490000-490d5cc0ad1eca76d44e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4r-0696000000-1df7921eb1369fef69c4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00dj-3960000000-e9ee044790c0655981b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-01ot-0904000000-dbbc479b104fbe981ce7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0903000000-c84b561c97b1277fed56	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0903000000-b498846e21073040b905	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0900000000-b04e175289861dc518f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0900000000-b04e175289861dc518f1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-01ot-0904000000-dbbc479b104fbe981ce7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0903000000-c84b561c97b1277fed56	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-0002-0903000000-b498846e21073040b905	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-006w-0719000000-d4feef3f83ca022aa94d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0913000000-3c8e5afb526637f1e822	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0910000000-57f268bed9b190ee6066	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-cfdda545a27ec16c8b76	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-c70817ad99741f01b675	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00di-0009000000-ecbabc9fe90444b14afe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-05fr-0019000000-4161bdd8f3deed25b9bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-002r-0594000000-bf4495b7906d53ad019d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00ds-0980000000-c4e88ec70fa28252f6f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0009000000-6926653590903a3ace6c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06vl-0019000000-301b3962f9291bee1ee9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0g4r-1294000000-8f3712f110452655373e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0009000000-a4ddb0d0eed36d96b76f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05uu-1009000000-badd4f30582cf375bbdf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8019000000-2bad3a1904cfc0e5431f	Spectrum

Toxicity Profile

Route of Exposure

80-90%

Mechanism of Toxicity

Dexamethasone 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.

Metabolism

Hepatic.

Toxicity Values

Oral, 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 Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Injection: 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 Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Status	Value	Unit	Sample Location	Reference

External Links

DrugBank ID

DB01234

HMDB ID

HMDB0015364

FooDB ID

FDB001355

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not 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.

MSDS

Not 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

Dexamethasone (CHEM003936)

Structure for CHEM003936: Dexamethasone