Desoximetasone CAS 382-67-2
Introduction：Basic information about Desoximetasone CAS 382-67-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Desoximetasone Basic information
| Product Name: | Desoximetasone |
| Synonyms: | 9-FLUORO-11BETA,21-DIHYDROXY-16ALPHA-METHYLPREGNA-1,4-DIENE-3,20-DIONE;9-fluoro-11b,21-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione;21-desoxybetamethasone;1,4-PREGNADIEN-9-ALPHA-FLUORO-16-ALPHA-METHYL-11-BETA, 21-DIOL-3,20-DIONE;DESOXIMETASONE;DESOXYMETASONE;Dexamethasone Impurity EP-F;DESOXIMETASONE;A 41-304;17-DEOXY DEXAMETHASONE;HOE 304 |
| CAS: | 382-67-2 |
| MF: | C22H29FO4 |
| MW: | 376.46 |
| EINECS: | 206-845-3 |
| Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals;Steroid and Hormone;Steroids |
| Mol File: | 382-67-2.mol |
Desoximetasone Chemical Properties
| Melting point | 213-215°C |
| alpha | D +109° (chloroform) |
| Boiling point | 532.3±50.0 °C(Predicted) |
| density | 376.46 |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| pka | 12.98±0.10(Predicted) |
| form | Solid |
| color | White to Off-White |
| InChIKey | VWVSBHGCDBMOOT-SDKBDWEQNA-N |
| SMILES | [C@@]12([H])CCC3=CC(=O)C=C[C@]3(C)[C@@]1(F)[C@@H](O)C[C@]1(C)[C@H]([C@H](C)C[C@@]21[H])C(=O)CO |&1:0,10,12,14,17,19,20,23,r| |
| CAS DataBase Reference | 382-67-2(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20/21/22-36/37/38-40-43 |
| Safety Statements | 22-26-36 |
| WGK Germany | 3 |
| RTECS | TU3834000 |
| HS Code | 29147000 |
| Description | Desoximetasone is a glucocorticoid.1 In vivo, desoximetasone (0.001-0.1 mg) reverses increases in epidermal cell proliferation induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) in SENCAR mice when administered topically. It also reduces TPA-induced expression of IL-6, COX-2, iNOS, and c-Jun mRNA levels in the skin of SENCAR mice, indicating anti-inflammatory action. Formulations containing desoximetasone have been used in the treatment of psoriasis and atopic dermatitis.WARNING This product is not for human or veterinary use. |
| Chemical Properties | Off-White Solid |
| Originator | Topicorte,Roussel,France,1968 |
| Definition | ChEBI: Dexamethasone in which the hydroxy group at the 17alpha position is substituted by hydrogen. A synthetic corticosteroid with glucocorticoid activity, it is used as an anti-inflammatory and anti-pruritic in the treatment of various skin disrders, including skin allergies and psoriasis. |
| Manufacturing Process | (a) Production of 16α-Methyl-4-Pregnene-11β,21-diol-3,20-Dione (= 16αMethylcorticosterone): A fermenter of stainless steel having a 50 liter capacityis charged with 30 liters of a nutrient solution containing: sterilized for ? hour at 120°C and after cooling, inoculated with a sporesuspension of Curvularia lunata which is obtained by rinsing a seven day cornculture (15 grams corn) with approximately 100 cc of physiological sodiumchloride solution. After two days of culturing at 25°C under stirring (220 revolutions per minute)and ventilating (1.65 m3/hr), 18 liters of the obtained culture are removedunder sterile conditions and introduced into a fermenter of the same sizecharged with 28.2 liters of a nutrient solution containing: After 24 hours cultivation under stirring and ventilation as described above,7.5 grams of 16α-methyldesoxycorticosterone, obtained by saponification ofthe corresponding 21-acetate and melting at 102-104°C, in 200 cc of ethanolare added and fermented under the same conditions for 28 hours. The course of the fermentation is tested by removal of samples, which areextracted with methyl isobutyl ketone. The extract is analyzed by paperchromatography in a system of dioxane + toluene/propylene glycol. After the end of the fermentation (28 hours) the culture broth is filtered off bysuction over a large suction filter. The mycel residue is washed with waterseveral times. The filtrate is extracted three times, each time with 10 liters ofmethyl isobutyl ketone. The extract is concentrated under vacuum in acirculating evaporator and in a round flask carefully dried under vacuum. Theresidue is crystallized from acetone/isopropyl ether. The melting point is 157-158°C (fermentation yield = 60%). The pure product yield obtained after asecond crystallization and chromatography of the mother liquor on silica gelamounts to 53% of the theoretical. (b) 16α-Methyl-9α-Fluoro-?4-Pregnene-11β,21-Diol-3,20-Dione: 7.5 grams of16α-methyl-9α-fluoro-?4-pregnene-21-ol-3,20-dione-21-acetate, obtainedfrom Step (a) by acetylating with acetic anhydride in pyridine followed byreaction with HF in pyridine at 0°C, are fermented for 36 hours withCurvularia lunata (Mutant NRRL 2380), whereby the 21-acetate group issimultaneously saponified, and then further worked up. The residue isextracted with MIBK, subjected to chromatography on silica gel and there isobtained from chloroform/ethyl acetate (2:1) an eluate containing the 11βhydroxy compound, which is further dehydrogenated as the crude product. (c) 16α-Methyl-9α-Fluoro-?1,4-Pregnadiene-11β,21-Diol-3,20-Dione: 16αmethyl-9α-fluoro-β4-pregnene-11β,21-diol-3,20-dione obtained as the crudeproduct under Step (b) above, is fermented with Bacillus lentus for 30 hoursand further worked up. The residue is extracted with methyl isobutyl ketoneand there is obtained as the crude product 16α-methyl-9α-fluoro-?1,4-pregnadiene-11β,21-diol-3,20-dione. |
| Brand name | Topicort (Taro) [Name previously used: Desoxymethasone.]. |
| Therapeutic Function | Antiinflammatory |
| General Description | Desoximetasone, 9-fluoro-11β, 21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione, like clocortolone pivalate, lacks a C17α OH group inits structure. |
Desoximetasone Preparation Products And Raw materials
| Raw materials | hydrogen fluoride-->D-Glucose monohydrate-->Acetic anhydride-->Dexamethasone |
