13649-88-2
Deflazacort
CAS: 14484-47-0;13649-88-2
Molecular Formula: C25H31NO6
13649-88-2 - Names and Identifiers
| Name | Deflazacort |
| Synonyms | deflan calcort azacort Denazacort Deflazacort 11b,21-Dihydroxy-2'- DEFLAZACORT INTERMEDIATE 16-d)oxazole-3,20-dione,11-beta,21-dihydroxy-2'-5'-beta-h-pregna-4-dieno(17 (11β,16β)-11-hydroxy-2-methyl-5β-H-progna-1,4-dieno[17,16-d]Oxazolo-3,20-dione (5'β)-21-Acetyloxy-11β-hydroxy-2'-methylpregnano[17,16-d]oxazole-1,4-diene-3,20-dione 11b,21-Dihydroxy-2'-methyl-5'bH-pregna-1,4-dieno[17,16-d]oxazole-3,20-dione 21-acetate (5'β)-11β-Hydroxy-21-acetyloxy-2'-methyl-1,2,4,5-tetradehydropregnano[17,16-d]oxazole-3,20-dione (4AR,4BS,5S,6AS,9AR,10AS,10BS)-6B-ACETYL-5-HYDROXY-4A,6A,8-TRIMETHYL-4A,4B,5,6,6A,6B,9A,10,10A,10B,11,12-DODECAHYDRO-9-OXA-7-AZA-PENTALENO[2,1-A]PHENANTHREN-2-ONE |
| CAS | 14484-47-0 13649-88-2 |
| EINECS | 238-483-7 |
| InChI | InChI=1/C23H29NO4/c1-12(25)23-19(28-13(2)24-23)10-17-16-6-5-14-9-15(26)7-8-21(14,3)20(16)18(27)11-22(17,23)4/h7-9,16-20,27H,5-6,10-11H2,1-4H3/t16-,17-,18-,19+,20+,21-,22-,23?/m0/s1 |
13649-88-2 - Physico-chemical Properties
| Molecular Formula | C25H31NO6 |
| Molar Mass | 441.52 |
| Density | 1.41 |
| Melting Point | 255-256.5°C |
| Boling Point | 595.4±50.0 °C(Predicted) |
| Specific Rotation(α) | D +62.3° (c = 0.5 in chloroform) |
| Flash Point | 282.9°C |
| Solubility | DMSO: ≥20mg/mL |
| Vapor Presure | 4.13E-14mmHg at 25°C |
| Appearance | powder |
| Color | white to tan |
| Merck | 14,2862 |
| pKa | 14.30±0.70(Predicted) |
| Storage Condition | 2-8°C |
| Refractive Index | 1.675 |
| Physical and Chemical Properties | Acetone-hexane crystals, melting point 255-256.5 °c. [Α] D 62.3 °(C = 0.5, chloroform). UV maximum absorption (methanol):241~242nm(E1 cm152.5). Acute toxicity LD50 mice (mg/kg):5200 oral; 1610 subcutaneous injection. Acute toxicity LD50 rats (mg/kg):109 subcutaneous injection. Acute toxicity LD50 dog (mg/kg):>4000 oral; 50 subcutaneous. |
13649-88-2 - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | TU4157050 |
| HS Code | 29349990 |
| Toxicity | LD50 orally in mice: 5200 mg/kg (Schiatti) |
13649-88-2 - Nature
Open Data Verified Data
crystallized from acetone-hexane, melting point 255-256.5 °c.
Last Update：2024-01-02 23:10:35
13649-88-2 - Preparation Method
Open Data Verified Data
3-hydroxy-2 '-methyl -5' H-nonando [17,16-d] n-oxazole-11, 20-= ketoxane in methanol, the aqueous solution of semicarbazide hydrochloride and pyridine was added, and the compound obtained by the reaction was dissolved in 95% ethanol. The aqueous solution of potassium carbonate and sodium borohydride were added, and the refluxing reaction was carried out. Should be. The reduced product was dissolved in methanol-hydrochloric acid and hydrolyzed under reflux. The product obtained by hydrolysis was dissolved in anhydrous toluene and cyclohexanone, and the reaction was carried out by adding triisopropylaluminum. The reaction product is dissolved in anhydrous dioxane, heated together with the acetic acid solution of hydrogen bromide, and the bromine dioxane solution is added. After the reaction, the reaction solution is put into water, and the obtained crystal is dried and then dissolved in dimethylformamide, A mixture of lithium bromide and lithium carbonate was added and reacted by heating to obtain a 1, 4-diene compound. The compound is dissolved in a mixed solution of tetrahydrofuran and methanol, added with calcium oxide and azobisisobutyronitrile, and then added with iodine in a mixed solution of tetrahydrofuran methanol, and iodination reaction is carried out. The resulting iodinated product was dissolved in acetone, triethylamine, acetone and acetic acid were added, and the reaction gave divot.
Last Update：2022-01-01 09:23:58
13649-88-2 - Use
Open Data Verified Data
Gruppo Lepetit S. p. A. Third-generation glucocorticoids. Anti-inflammatory, anti-allergic, increased gluconeogenesis and other effects. For primary and secondary adrenal hypofunction, rheumatism, collagen disease, skin disease, allergic disease, eye disease, fulminant and disseminated tuberculosis, hematopoietic disorders, ulcerative colitis, idiopathic nephrotic syndrome, malignant tumor of hematopoietic system, etc.
Last Update：2022-01-01 09:23:59
13649-88-2 - Safety
Open Data Verified Data
mouse oral LD50:5200mg/kg.
Last Update：2022-01-01 09:23:59
13649-88-2 - Reference Information
| pharmacological effects | difkot is the third generation glucocorticoid, which has anti-inflammatory, anti-allergic, increased glycogen eogenesis and other effects. The effect is equivalent to 10~20 times that of prednisolone and 40 times that of hydrocortisone. This product has no mutagenic effect. The research of C14 labeled this product shows that the gastrointestinal tract of this product is absorbed rapidly, and the blood concentration peaks after 1~2 h, and the active substance is formed by hydrolysis. The further metabolic process of the latter is similar to other glucocorticoids. The T1/2 of the active metabolite is 2 h, which is mainly distributed in the kidney and hematopoietic system and other tissues in rats. Figure 1 is the structural formula of Divkot. |
| indications | for primary or secondary adrenal hypofunction, rheumatism, collagen diseases, hematopoietic diseases, ulcerative colitis, idiopathic nephrotic syndrome, hematopoietic malignant tumors, allergic and allergic diseases, and anti-tuberculosis drugs to treat fulminant and disseminated tuberculosis. |
| usage and dosage | adult dose is generally po,6~90mg/d, and the specific dose is determined according to the disease condition. |
| adverse reactions | long-term medication can affect the normal growth of children, induce peptic ulcer perforation, and cause euphoria, depression, insomnia and other mental symptoms. Sudden withdrawal after long-term application can cause withdrawal reaction of secondary adrenal insufficiency, which should be gradually reduced until withdrawal. |
| precautions | (1) like other glucocorticoids, it is prohibited from systemic infectious diseases. (2) Be careful for diverticulitis, recent gastrointestinal surgery, renal failure, hypertension, diabetes, osteoporosis, myasthenia gravis and other diseases. Use with caution in pregnant and lactating women. |
| drug interaction | 1. divor can have specific potassium excretion effect, which should be paid attention to when combined with diuretics. 2. In combination with drugs with enzymatic effects (rifampicin, phenobarbital, etc.), glucocorticoids should be appropriately increased. 3. Erythromycin and estrogen can inhibit the metabolism of this product and active substances, and should be reduced when combined. |
| use | the third generation glucocorticoid has anti-inflammatory, anti-allergic, increased glycogen eogenesis and other effects. For primary and secondary adrenal hypofunction, rheumatism, collagen diseases, skin diseases, allergic diseases, ophthalmic diseases, fulminant and disseminated tuberculosis, hematopoietic system diseases, ulcerative colitis, idiopathic nephrotic syndrome, hematopoietic system malignant tumors, etc. |
| production method | 10g compound (I) is dissolved in 350ml of methanol, 8.3g of semicarbazide hydrochloride and 5.75ml of pyridine in 50ml of water are added to react to obtain 11g compound (II). 9g of compound (II) is dissolved in 230ml of 95% ethanol, 3.6g of potassium carbonate solution in 36ml of water and 2.34g of sodium borohydride are added, and 2.34g of sodium borohydride is added after reflux for 30min to obtain 8.5g of compound (III). 7.7g compound (Ⅲ) was dissolved in 154ml methanol-10% hydrochloric acid and refluxed for 1h to obtain 6g compound (Ⅳ). 12.5g of compound (Ⅳ) was dissolved in 500ml of anhydrous toluene and 90ml of cyclohexanone, and 6.24g of triisopropyl aluminum was added to react to obtain 9g of compound (V). 6.5g compound (V) is dissolved in 123ml of anhydrous dioxane, heated with acetic acid solution 25% hydrogen bromide, and then added with 5.5g of bromine dioxane solution; After the reaction, the reaction liquid is poured into water, the crystals of the filter set are carefully dried, then dissolved in dimethylformamide, a mixture of 7.5g of lithium bromide and lithium carbonate (1:2) is added, and 5.1g of compound (VI) is obtained by heating the reaction. 2g of compound (Ⅵ) is dissolved in tetrahydrofuran-methanol (1:1), 3.9g of calcium oxide and 0.1g of azobisisobutyronitrile are added, and 2g of iodine is added in the mixed solution of tetrahydrofuran-methanol. After the reaction, the precipitate is filtered out, dissolved in acetone, 20ml of triethylamine, 20ml of acetone and 12ml of acetic acid are added, and 1.6g of difkot is obtained by reaction. |
Last Update：2024-04-10 22:29:15
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Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple Specifications
Product Name: Deflazacort Request for quotationCAS: 13649-88-2
Tel: 0086-551-65418684
Email: sales@tnjchem.com
info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840
Wechat: 0086 189 4982 3763
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