Record Information |
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Version | 1.0 |
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Creation Date | 2014-10-14 21:18:42 UTC |
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Update Date | 2016-10-28 10:04:08 UTC |
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Accession Number | CHEM003936 |
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Identification |
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Common Name | Dexamethasone |
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Class | Small Molecule |
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Description | An anti-inflammatory 9-fluoro-glucocorticoid. [PubChem] |
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Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
- STOFF IDENT Compounds
- Suspected Compounds - Waste Water
- Suspected Compounds – Schymanski Project
- T3DB toxins
- ToxCast & Tox21 Chemicals
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Contaminant Type | - Anti-Inflammatory Agent
- Antiemetic
- Antineoplastic Agent, Hormonal
- Drug
- Glucocorticoid
- Metabolite
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C22H29FO5 |
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Average Molecular Mass | 392.461 g/mol |
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Monoisotopic Mass | 392.200 g/mol |
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CAS Registry Number | 50-02-2 |
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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 |
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Traditional Name | dexamethasone |
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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 |
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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 |
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InChI Key | UREBDLICKHMUKA-CXSFZGCWSA-N |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Hydroxysteroids |
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Direct Parent | 21-hydroxysteroids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | 170-229 °C | Boiling Point | Not Available | Solubility | 89 mg/L (at 25 °C) |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS | splash10-02ai-2923000000-e31987dc12e5a702a42e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) | splash10-0006-2414490000-490d5cc0ad1eca76d44e | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0a4r-0696000000-1df7921eb1369fef69c4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-00dj-3960000000-e9ee044790c0655981b1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-01ot-0904000000-dbbc479b104fbe981ce7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0002-0903000000-c84b561c97b1277fed56 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0002-0903000000-b498846e21073040b905 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0002-0900000000-b04e175289861dc518f1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0002-0900000000-b04e175289861dc518f1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-01ot-0904000000-dbbc479b104fbe981ce7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0002-0903000000-c84b561c97b1277fed56 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , negative | splash10-0002-0903000000-b498846e21073040b905 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-006w-0719000000-d4feef3f83ca022aa94d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0913000000-3c8e5afb526637f1e822 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0910000000-57f268bed9b190ee6066 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0900000000-cfdda545a27ec16c8b76 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0002-0900000000-c70817ad99741f01b675 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00di-0009000000-ecbabc9fe90444b14afe | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-05fr-0019000000-4161bdd8f3deed25b9bc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-002r-0594000000-bf4495b7906d53ad019d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-00ds-0980000000-c4e88ec70fa28252f6f7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002f-0009000000-6926653590903a3ace6c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06vl-0019000000-301b3962f9291bee1ee9 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0g4r-1294000000-8f3712f110452655373e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0009000000-a4ddb0d0eed36d96b76f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-05uu-1009000000-badd4f30582cf375bbdf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-8019000000-2bad3a1904cfc0e5431f | View in MoNA |
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Toxicity Profile |
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Route of Exposure | 80-90% |
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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. |
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Metabolism | Hepatic. |
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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. |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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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 |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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| Status | Value | Unit | Sample Location | Reference |
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External Links |
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DrugBank ID | DB01234 |
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HMDB ID | HMDB0015364 |
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FooDB ID | FDB001355 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Dexamethasone |
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Chemspider ID | 5541 |
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ChEBI ID | 41879 |
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PubChem Compound ID | 5743 |
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Kegg Compound ID | C15643 |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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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. |
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MSDS | Not Available |
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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 |
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