| Name | Dexamethasone |
|---|---|
| Synonyms | DEXAMETHASONE BASE; DEXAMETHASONUM; DEXAMETHASON; DEXAMETHASONE; CALONAT; (11BETA,16ALPHA)-9-FLUORO-11,17,21-TRIHYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE; (11B,16A)-9-FLUORO-11,17,21-TRIHYDROXY-16-METHYL-PREGNA-1,4-DIENE-3,20-DIONE;1,4-PREGNADIEN-9ALPHA-FLUORO-16ALPHA-METHYL-11BETA, 17ALPHA, 21-TRIOL 3,20-DIONE (11B,16A)-9-FLUORO-11,17,21-TRIHYDROXY-16-METHYL-PREGNA-1,4-DIENE-3,20-DIONE (11BETA,16ALPHA)-9-FLUORO-11,17,21-TRIHYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE 1,4-PREGNADIEN-9-ALPHA-FLUORO-16-ALPHA-METHYL-11-BETA, 17,21-TRIOL-3,20-DIONE 1,4-PREGNADIEN-9ALPHA-FLUORO-16ALPHA-METHYL-11BETA, 17ALPHA, 21-TRIOL 3,20-DIONE 1,4-PREGNADIENE-3,20-DIONE-9ALPHA-FLUORO-16ALPHA METHYL-11BETA,17ALPHA,21-TRIOL 9ALPHA-FLUORO-11BETA,17,21-TRIHYDROXY-16ALPHA-METHYL-1,4-PREGNADIENE 3,20DIONE 9ALPHA-FLUORO-11BETA,17ALPHA,21-TRIHYDROXY-16ALPHA-METHYLPREGN-1,4-DIENE-3,20-DIONE 9ALPHA-FLUORO-16ALPHA-METHYL-11BETA,17ALPHA,21-TRIHYDROXY-1,4-PREGNADIENE-3,20-DIONE 9ALPHA-FLUORO-16ALPHA-METHYLPREDNISOLONE CALONAT DECACORTIN DECADRON DECASONE DERONIL DEXAMETHASON DEXAMETHASONE DEXAMETHASONE BASE DEXAMETHASONUM HEXADECADROL PREDNISOLONE F |
| CAS NO | 50-02-2 |
| EINECS | 200-003-9 |
| Molecular Weight | 392.46 |
| Molecular Formula | C22H29FO5 |
| Product Categories | Active Pharmaceutical Ingredients; Antitumors for Research and Experimental Use; Biochemistry; Hydroxyketosteroids; Steroids; Isotope Labeled Compounds; Intermediates & Fine Chemicals; Pharmaceuticals; Pharmaceutical intermediates; pharmaceutical intermediate and medicine grade; Steroid and Hormone; Pharmaceutical intermediate; API; Mainly used for anti-inflammatory and allergy; MAXIDEX; Hormone Drugs |
| Mol File | 50-02-2.mol |
Dexamethasone Chemical Properties | |
|---|---|
| Melting point | 262-264 °C(lit.) |
| alpha | 75 º (c=1, dioxane) |
| Fp | 9℃ |
| refractive index | 76 ° (C=1, Dioxane) |
| density | 1.1283 (estimate) |
| storage temp | 2-8°C |
| solubility | ethanol: 1 mg/mL |
| form | powder |
| Water Solubility | 10 mg/100 mL (25 ºC) |
| Merck | 14,2943 |
| BRN | 2066651 |
| color | off-white |
| Sensitive | Light Sensitive |
| Stability | Stable. Combustible. Incompatible with strong oxidizing agents, strong bases, acid anhydrides, acid chlorides. May be light sensitive. |
| CAS DataBase Reference | 50-02-2(CAS DataBase Reference) |
| InChIKey | UREBDLICKHMUKA-CXSFZGCWSA-N |
| Safety Information | |
|---|---|
| Hazard Codes | Xi,Xn,T,F |
| Risk Statements | 43-40-36/37/38-20/21/22-42/43-39/23/24/25-23/24/25-11 |
| Safety Statements | 36/37-45-36-26-22-16 |
| RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution |
| WGK Germany | 2 |
| RTECS | TU3980000 |
| TSCA | Yes |
| HS Code | 29372210 |
| Toxicity | LD50 oral in rat: > 3gm/kg |
| Hazardous Substances Data | 50-02-2(Hazardous Substances Data) |
| Dexamethasone Usage And Synthesis | |
|---|---|
| Description | Dexamethasone is an Anti-inflammatory glucocorticoid that is used to treat inflammatory and autoimmune conditions such as rheumatoid arthritis and bronchospasm. It is useful to study apoptosis, cell signaling pathways and gene expression. It is associated with marbofloxacin and clotrimazole and finds application in veterinary medicine to treat difficult ear infections in dogs. It is also used to treat horses with swelling of of distal limbs and general bruising in combination with trichlormethiazide. Dexamethasone induces the production of phospholipase A2 inhibitory protein (lipocortin). It also inhibits induction of nitric oxide synthase (IC50=5 nM). Dexamethasone has been shown to cause reduction in cyclin A and Cd k2 activity, inhibition of G1/S transition in osteoblasts and inhibition of phosphorylation of Rb protein in vitro. Dexamethasone has been observed to induce apoptosis in human thymocytes and eosinophils, but inhibits apoptosis in neutrophils in vitro. Dexamethasone is an activator of IDO. Dexamethasone Inhibits the expression of the inducible but not the constitutive nitric oxide synthase in vascular endothelial cells (IC50=5 nM). Dexamethasone regulates T cell survival, growth, and differentiation.Enhances active cation transport in aortic smooth muscle cells by stimulating the Na+-K+ pump. Has anti-inflammatory and anti-rheumatic properties. Induces apoptosis in human thymocytes. In general, 500-1000 nM of dexamethasone is sufficient to induce apoptosis following a 6-hour incubation at 37°C. |
| Side Effects | Dexamethasone is a artificially synthetic glucocorticoid, belonging to a long-term glucocorticoid drugs. Glucocorticoids can promote the metabolism of the three major nutrients while preventing protein synthesis with long-term topical being able to causing more serious consequences. However, the adverse effects should be much smaller than oral medication. Common side effects of systemic corticosteroid include: It can cause stomach discomfort and increased sensitivity to stomach ulcers. It can Increase the appetite and results in a significant increase in body weight. Potential patients with diabetes: glucose intolerance in patients with aggravating existing diabetes. It can cause mental illness including personality changes, irritability, agitation, and mania. It can be used for the long-term treatment of osteoporosis: pathological fractures (such as hip). It can cause elevated liver enzymes, fatty liver degeneration (usually reversible). For patients of nephrotic syndrome, applying long-term high-dose medication is likely to cause large side effects such as gastrointestinal ulcers and avascular necrosis. For treatment of nephrotic syndrome, it is better to apply prednisone acetate tablets. Dexamethasone can be used for the treatment of high altitude cerebral edema and pulmonary edema. Upon climbing expeditions, people can apply it to alleviate altitude sickness. Combination with marbofloxacin and clotrimazole, etc. can be used for treating the ear infection and allergies of a dog or a bird. The above information is edited by the chemicalbook of Dai Xiongfeng. |
| Drug Reactions | Dexamethasone is a corticosteroid known as a glucocorticoid. Corticosteroids are meant to resemble a naturally occurring hormone produced in the adrenal cortex, cortisol. Corticosteroids act on the immune system by blocking the production of substances that trigger inflammatory and immune responses. Dexamethasone may react with these drugs: Amphotericin Aspirin Cyclophosphamide Cyclosporine Digoxin Daunorubicin HCl Doxorubicin HCl Insulin Mitotane Phenobarbital Phenytoin sodium Rifampin Rimadyl |
| Description | The activity of dexamethasone, as measured by glycogen deposition, is 20 times greater than that of hydrocortisone. It has five times the anti-inflammatory activity of prednisolone. Clinical data indicate that this compound has seven times the antirheumatic potency of prednisolone. It is roughly 30 times more potent than hydrocortisone. Its pharmacokinetics are presented in Table 33.3. Routes of metabolism for dexamethasone are similar to those for prednisolone, with its primary 6β-hydroxy metabolite being recovered in urine. Dexamethasone sodium phosphate is the water-soluble sodium salt of the 21-phosphate ester, with an IV half-life of less than 10 minutes because of rapid hydrolysis by plasma phosphatases. Peak plasma levels for dexamethasone usually are attained in approximately 10 to 20 minutes following its IV administered dose. A similar reaction occurs when the phosphate ester is applied topically or by inhalation. |
| Chemical Properties | White or almost white, crystalline powder. |
| Uses | Glucocorticoid. |
| Indications | Cushing’s disease is defined as hypercortisolism due to chronic overproduction of corticotrophin by a corticotroph adenoma. Cortisol’s lack of suppressibility during the administration of low doses of dexamethasone but suppressibility during high-dose dexamethasone is the key diagnostic finding in 99% of the patients with Cushing’s disease. This contrasts with the lack of glucocorticoid suppressibility typically found in patients with corticotrophin-independent hypercortisolism (Cushing’s syndrome). A judicious selection of the available tests may be necessary to obtain an accurate diagnosis in patients with Cushing’s syndrome. |
| Brand name | Aeroseb-Dex (Allergan); Decadron (Merck); Dexone (Solvay Pharmaceuticals); Hexadrol (Organon); Maxidex (Alcon); Mymethasone (Morton Grove). |
| General Description | Odorless white to off-white crystalline powder with a slightly bitter taste. |
| General Description | Dexamethasone, 9-fluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione,is the 16 -isomer of betamethasone. Dexamethasone acetate, USP (21-acetate) Dexamethasone sodium phosphate, USP (21-sodiumphosphate). |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Dexamethasone may be sensitive to prolonged exposure to light. Dexamethasone is incompatible with strong oxidizers, strong acids, acid chlorides and acid anhydrides. Oxidation may occur with bases. |
| Fire Hazard | Flash point data for Dexamethasone are not available; however, Dexamethasone is probably combustible. |
| Biological Activity | Glucocorticoid; anti-inflammatory. Reduces levels of activated NF- κ B in immature dendritic cells (DCs) and inhibits differentiation into mature DCs. |
| Pharmacokinetics | The activity of dexamethasone, as measured by glycogen deposition, is 20 times greater than that of hydrocortisone. It has five times the anti-inflammatory activity of prednisolone. Clinical data indicate that this compound has seven times the antirheumatic potency of prednisolone. It is roughly 30 times more potent than hydrocortisone. Its pharmacokinetics are presented in Table 33.3. Routes of metabolism for dexamethasone are similar to those for prednisolone, with its primary 6β-hydroxy metabolite being recovered in urine. Dexamethasone sodium phosphate is the water-soluble sodium salt of the 21-phosphate ester, with an IV half-life of less than 10 minutes because of rapid hydrolysis by plasma phosphatases. Peak plasma levels for dexamethasone usually are attained in approximately 10 to 20 minutes following its IV administered dose. A similar reaction occurs when the phosphate ester is applied topically or by inhalation. |
| Safety Profile | Poison by intraperitoneal and subcutaneous routes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of F-. |
| Veterinary Drugs and Treatments | Glucocorticoids have been used in an attempt to treat practically every malady that afflicts man or animal, but there are three broad uses and dosage ranges for use of these agents. 1) Replacement of glucocorticoid activity in patients with adrenal insufficiency, 2) as an antiinflammatory agent, and 3) as an immunosuppressive. Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases (e.g., rheumatoid arthritis), collagen diseases (e.g., systemic lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic diseases (e.g., pemphigus, allergic dermatoses), hematologic disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias), neoplasias, nervous system disorders (increased CSF pressure), GI diseases (e.g., ulcerative colitis exacerbations), and renal diseases (e.g., nephrotic syndrome). Some glucocorticoids are used topically in the eye and skin for various conditions or are injected intra-articularly or intralesionally. The above listing is certainly not complete. For specific dosages and indications refer to the Doses section. High dose dexamethasone use for shock or CNS trauma is controversial; recent studies have not demonstrated significant benefit and it actually may cause increased deleterious effects. |
| Purification Methods | Dexamethasone has been recrystallised from Et2O or small volumes of EtOAc. |
| Dexamethasone Preparation Products And Raw materials | |
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