(1R,2S,10S,11S,13R,14R,15S,17S)-1-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

• ChemBase ID: 1103
• Molecular Formular: C22H29FO5
• Molecular Mass: 392.4610632
• Monoisotopic Mass: 392.19990225
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@@H](C3)C)C(=O)CO)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: 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
• InChIKey: UREBDLICKHMUKA-CXSFZGCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one; (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one; (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: dexamethasone
• Brand Name: Adexone; Aeroseb-D; Aeroseb-Dex; Anaflogistico; Aphtasolon; Aphthasolone; Auxiron; Azium; Bisu Ds; Calonat; Corson; Corsone; Cortisumman; Decacort; Decacortin; Decaderm; Decadron; Decadron Tablets, Elixir; Decadron-La; Decagel; Decalix; Decasone; Decaspray; Dectancyl; Dekacort; Deltafluorene; Dergramin; Deronil; Desadrene; Desameton; Deseronil; Dex-Ide; Dexa; Dexa Mamallet; Dexa-Cortidelt; Dexa-Cortisyl; Dexa-Mamallet; Dexa-Scheroson; Dexa-Sine; Dexacen-4; Dexacidin; Dexacort; Dexacortal; Dexacortin; Dexadeltone; Dexafarma; Dexair; Dexalona; Dexaltin; Dexameth; Dexamethasone Intensol; Dexamonozon; Dexapolcort; Dexapos; Dexaprol; Dexason; Dexasone; Dexinolon; Dexinoral; Dexone; Dexone 0.5; Dexone 0.75; Dexone 1.5; Dexone 4; Dexonium; Dextelan; Dezone; Dinormon; Fluormone; Fluorocort; Fortecortin; Gammacorten; Hexadecadrol; Hexadrol; Hexadrol Elixir; Hexadrol Tablets; Hl-Dex; Isopto-Dex; Lokalison F; Loverine; Luxazone; Maxidex; Maxitrol; Mediamethasone; Mexidex; Millicorten; Mymethasone; Ocu-Trol; Oradexon; Pet Derm Iii; Pet-Derm Iii; Policort; Prednisolon F; Prednisolone F; Sk-Dexamethasone; Spoloven; Sunia Sol D; Superprednol; Turbinaire; Visumetazone; Posurdex; IontoDex
• Synonyms: Desametasone [DCIT]; Desametasone; Desamethasone; Dexametasona [INN-Spanish]; Dexamethasone Acetate; Dexamethasone Sodium Phosphate; Dexamethasonum [INN-Latin]; Dexamethazone; Fluormethylprednisolone; Dexamethasone; Dexamethasonum; (1R,2S,10S,11S,13R,14R,15S,17S)-1-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; 16α-Methyl-9α-fluoroprednisolone; Aeroseb-Dex; Corson; Cortisumman; Decacort; Decaderm; Decalix; Decasone; Dekacort; (11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 9α-Fluoro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione; 9α-Fluoro-16α-methylprednisolone; Prednisolone F; Dexamethasone; 9α-Fluoro-16α-methylprednisolone; Decadron; 地塞米松; 21α-乙酰氧基-9α-氟-11β,17α-二羟基-16α-甲基孕甾-1,4-二烯-3,20-二酮; 9α-氟-16α-甲基氢化泼尼松; 9-氟-11,17,21-三羟基-16-甲基(11b,16a)-孕甾-1,4-二烯-3,20-二酮; 德沙美松; 地塞米松

Database IDs

• CAS Number: 50-02-2
• EC Number: 200-003-9
• MDL Number: MFCD00064136
• Beilstein Number: 2066651
• PubChem SID: 24893536; 24894235; 46508930; 24893906; 24894273; 24858929; 24869878; 160964566
• PubChem CID: 5743
• CHEBI ID: 41879
• ATC CODE: D07AB19; R01AD03; S03BA01; A01AC02; C05AA09; H02AB02; S01BA01; D10AA03; S02BA06
• CHEMBL: 384467
• Chemspider ID: 5541
• DrugBank ID: DB01234
• KEGG ID: D00292
• Unique Ingredient Identifier: 7S5I7G3JQL
• Wikipedia Title: Dexamethasone
• Medline Plus: a682792

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.423736
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6815696
• LogD (pH = 7.4): 1.6815655
• Log P: 1.6815697
• Molar Refractivity: 102.4929 cm^3
• Polarizability: 39.61867 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.93
• LOG S: -3.89
• Solubility (Water): 5.05e-02 g/l

PROPERTIES

Physical Property

• Solubility: 89 mg/L; Acetone; Dioxane; DMSO; Methanol
• Apperance: powder; White Solid
• Melting Point: 240-242°C (dec.); 253 - 255°C; 262-264 ; 268-271 °C; 262-264 °C(lit.)
• Optical Rotation: [α]20/D +76±4°, c = 1% in dioxane; [α]25/D +77.5° in dioxane
• Hydrophobicity(logP): 1.1; 1.785

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS: TU3980000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: IL receptor
• Admin Routes: Oral, IV, IM, SC and IO
• Bioavailability: 80-90%
• Excretion: renal
• Half Life: 36-54 hours
• Metabolism: hepatic
• Protein Bound: 70%
• Legal Status: Rx-only
• Pregnancy Category: C (US)
• Gene Information: human ... ABCB1(5243), CYP3A4(1576), IL4(3565), IL5(3567), NR3C1(2908)mouse ... Abcb1a(18671), Abcb1b(18669), Ifng(15978), Nos2(18126), Ptgs2(19225), Tnf(21926)rat ... Ar(24208), Nr3c1(24413), Tnf(24835); human ... NR3C1(2908)

Product Information

• Purity: ≥80% (HPLC); ≥97%; ≥97.0% (HPLC); 95%; 98%
• Grade: Ph Eur; VETRANAL™, analytical standard
• Salt Data: Free Base
• Potency: 4-500 ng/mL
• Suitability: meets USP testing specifications; suitable for cell culture
• Sterility: γ-irradiated
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C22H29FO5

DETAILS

MP Biomedicals - 02190040

Crystalline

MP Biomedicals - 02194561

Cell Culture Reagent
Crystalline

MP Biomedicals - 02194560

Cell Culture Reagent
γ-Irradiated
Crystalline

DrugBank - DB01234

• Drug Groups: approved; investigational
• Description: An anti-inflammatory 9-fluoro-glucocorticoid. [PubChem]
• Indication: 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
• Pharmacology: Dexamethasone and its derivatives, dexamethasone sodium phosphate and dexamethasone acetate, are synthetic glucocorticoids. 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.
• Toxicity: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: 80-90%
• Half Life: 36-54 hours
• Protein Binding: 70%
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1322

Research Area: Inflammation
Biological Activity:
Dexamethasone is a potent synthetic member of the glucocorticoid class of steroid drugs. It acts as an anti-inflammatory and immunosuppressant. Its potency is about 20-30 times that of the naturally occurring hormone hydrocortisone and 4-5 times of prednisone. [1]

Sigma Aldrich - D8893

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
一种抗炎糖皮质素，对细胞存活、细胞信号传导和基因表达具有一系列的影响。用于研究细胞凋亡、细胞信号传导通路和基因表达。
Reconstitution
要制备 20μg/ml 储备液：加入 1ml 无水乙醇，缓缓搅拌溶解，加入 49ml 无菌培养基。
Physical form
2-8°C 下为粉末状，分成小份冻存以避免使用时反复冷冻/解冻。
Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。

Sigma Aldrich - D157

Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。

Sigma Aldrich - D9184

Application
一种抗炎糖皮质素，对细胞存活、细胞信号传导和基因表达具有一系列的影响。用于研究细胞凋亡、细胞信号传导通路和基因表达。
Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。

Sigma Aldrich - D4902

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
An anti-inflammatory glucocorticoid with a range of effects on cell survival, cell signaling and gene expression. Use to study apoptosis, cell signaling pathways and gene expression.
Reconstitution
To prepare 20 μg/ml stock solution, add 1ml absolute ethanol per mg product; gently swirl to dissolve. Add 49 ml sterile medium per ml of ethanol added, while mixing, to acheive final concentration of 20 μg/ml.
Physical form
powder 2-8 °C; stock-frozen in working aliquots, avoid repeated freeze/thaw
Biochem/physiol Actions
糖皮质素抗炎剂。调控 T 细胞的存活、生长和分化。抑制一氧化氮合酶的诱导作用。

Sigma Aldrich - 861871

Packaging
100 mg in glass bottle
Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.

Sigma Aldrich - 46165

Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 31375

Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.

Sigma Aldrich - 31381

Other Notes
Useful for the induction of liver metallothionein1
Biochem/physiol Actions
Glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.

Toronto Research Chemicals - D298800

Dexamethasone is a glucocorticoid used as an anti-inflammatory agent. Dexamethasone regulates T cell survival, growth, and differentiation. Dexamethasone inhibits the induction of nitric oxide synthase.

REFERENCES

• http://www.rxlist.com/decadron-drug.htm
• Wershil, B.K., et al.: Int. Arch. Allergy Immunol., 107, 323 (1995)
• Riccardi, C., et al.: Cell Death Diff., 6, 1182 (1995)
• Llanos, S.L. and Roldan, A.: Bio Cell, 23, 29 (1999)