1177-87-3 Usage
Description
Dexamethasone-17-acetate, also known as Decadron, is a synthetic glucocorticoid with potent anti-inflammatory and immunosuppressive properties. It is a derivative of dexamethasone, an active metabolite of prednisolone, and is characterized by its off-white solid appearance. Dexamethasone-17-acetate is used in various medical applications due to its ability to modulate immune responses and reduce inflammation.
Used in Pharmaceutical Industry:
Dexamethasone-17-acetate is used as a pharmaceutical primary standard for quantifying the analyte in pharmaceutical formulations using chromatography techniques. This ensures the accurate measurement and quality control of the drug in various formulations.
Used in Medical Treatments:
Dexamethasone-17-acetate is used as an anti-inflammatory and immunosuppressive agent for various medical conditions. It is used to treat or prevent allergic reactions, autoimmune diseases, skin conditions, asthma, and other lung conditions. It is also used in the treatment of various cancers, such as leukemia, lymphoma, and multiple myeloma.
Used in Cancer Treatment:
Dexamethasone-17-acetate is used as an adjunct therapy in cancer treatment, particularly in the management of side effects and inflammation associated with cancer and its treatments. It has been observed to decrease the number of activated macrophages and significantly reduce mRNA levels of TPH2 (tryptophan hydroxylase-2) in the raphe nuclei of C57/Bl6 mice, suggesting its potential role in modulating immune responses in cancer.
Used in Adrenal Insufficiency:
Dexamethasone-17-acetate is used as a replacement therapy in adrenal insufficiency, a condition where the adrenal glands do not produce enough hormones. It helps to maintain normal hormone levels and alleviate symptoms associated with the condition.
Used in Cushing's Syndrome Diagnosis:
Dexamethasone-17-acetate is used in a screening test for the diagnosis of Cushing's syndrome, a hormonal disorder caused by prolonged exposure to high levels of cortisol. The test helps to determine if the body's cortisol production is regulated properly.
Originator
Dexacen,Central,US,1977
Manufacturing Process
The preparation of dexamethasone acetate is described in US Patent
3,007,923 as follows. 1.5 cc of dimethylformamide and 1.5 cc of anhydrous
hydrofluoric acid are admixed and treated with 480 mg of 9β,11β-epoxy-17αhydroxy-21-acetoxy-16α-methyl-?1,4-pregnadiene-3,20-dione (prepared
according to E.P. Oliveto et al, J. Am. Chem. Soc., 80, 44331, 1958). The
steroid dissolves in about 15 minutes. The reaction mixture is shaken for two
hours at a temperature between 0 and +5°C, and then poured into 75 cc ofwater containing in suspension, 7.5 grams of sodium bicarbonate. The mixture
is vacuum filtered, the filter cake washed and then dried at 100°C, yielding
460 mg of crude hexadecadrol contaminated with a small amount of the
starting material. A single recrystallization from methylene chloride yields 370
mg of the pure product having a melting point of 170°C and 229°C. The
mother liquor yields 62 mg of the starting material, and a remainder
constituting a mixture of starting and final materials with little other
contamination.
Therapeutic Function
9-Fluoro-11β,17-dihydroxy-21-acetoxy-16α-methylpregna1,4-diene-3,20-dione
Safety Profile
Experimental
teratogenic and reproductive effects. A
steroid. When heated to decomposition it
emits toxic fumes of F-.
Purification Methods
Dexamethasone 21-acetate is purified on neutral Al2O3 using CHCl3 as eluent, the fractions are evaporated, and the residue is recrystallised from CHCl3. It has max at 239nm. [Oliveto et al. J Am Chem Soc 8 0 4431 1958]. [Beilstein 8 IV 3501.]
Check Digit Verification of cas no
The CAS Registry Mumber 1177-87-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,7 and 7 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 1177-87:
(6*1)+(5*1)+(4*7)+(3*7)+(2*8)+(1*7)=83
83 % 10 = 3
So 1177-87-3 is a valid CAS Registry Number.
InChI:InChI=1/C24H31FO6/c1-13-9-18-17-6-5-15-10-16(27)7-8-21(15,3)23(17,25)19(28)11-22(18,4)24(13,30)20(29)12-31-14(2)26/h7-8,10,13,17-19,28,30H,5-6,9,11-12H2,1-4H3/t13-,17?,18?,19+,21+,22+,23+,24+/m1/s1
1177-87-3Relevant articles and documents
C21 steroid 21 site acetylation process
-
Paragraph 0022-0024, (2018/11/22)
The invention discloses a C21 steroid 21 site acetylation process. C21 steroid is prednisolone, hydrocortisone, dexamethasone or betamethasone; the C21 steroid is subjected to acetylation with aceticanhydride; the acetylation of the C21 steroid with the acetic anhydride is carried out in a mixed solvent; an acetic acid alkali metal salt is adopted as a catalyst, and the reaction is carried out inthe presence of an inert gas; the mixed solvent is a mixed solvent of tetrahydrofuran and acetone; the weight ratio of the tetrahydrofuran to the acetone in the mixed solvent is (2-9):1. High-toxicity and high ammonia nitrogen pyridine and dimethylformamide are replaced by using the mixed solvent of tetrahydrofuran and acetone without ammonia nitrogen, no high ammonia nitrogen wastewater is generated, and environment pollution can be reduced.
Preparation technology for dexamethasone sodium phosphate
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Paragraph 0014, (2016/10/08)
The invention relates to a preparation technology for dexamethasone sodium phosphate. The preparation technology comprises the following steps: a ring-opening reaction is carried out, namely, dexamethasone acetate epoxide is employed as an initial raw material, HF and DMF are added, a reaction is performed for 3h, a ring-opening reaction is carried out and a dexamethasone acetate solution is prepared; recrystallization is carried out, namely, acetone or ether is added in the dexamethasone acetate solution, recrystallization is carried out, dexamethasone acetate is prepared, and rotary distillation is employed to remove the solvent after recrystallization; base catalysis hydrolysis is carried out, namely, dexamethasone acetate is added in Na2CO3 and methanol, a reaction is carried out for 10min, dexamethasone is prepared; pyrophosphoryl chlorine esterification is carried out, namely, dexamethasone is reacted with pyrophosphoryl chlorine and THF, and dexamethasone phosphate ester is prepared; a neutralization salt forming reaction is carried out, namely, the dexamethasone phosphate ester obtained from the fourth step is reacted with NaOH and methanol, and dexamethasone sodium phosphate is prepared. The steps are simple, raw materials are easily available, the reaction conditions are mild, the preparation technology is suitable for industrial production, and the cost is low.
16α-methylation process
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, (2008/06/13)
Disclosed is a process for the production of a Δ17(20) -steroid of the formula STR1 which comprises starting with a 16-unsaturated corticoid of the formula STR2 and contacting the 16-unsaturated corticoid (I) with a methylating agent in the presence of a copper catalyst and a silylating agent.
