53-03-2 Usage
Description
Prednisone, also known as Δ1-cortisone, 17,21-dihydroxypregna-1,4-diene-3,11,20-trione, is a synthetic glucocorticoid drug that is particularly effective as an immunosuppressant. It affects virtually all aspects of the immune system and is a prodrug that is converted by the liver into prednisolone, which is the active drug and also a steroid. Prednisone has systemic activity very similar to that of prednisolone and is often preferred over cortisone or hydrocortisone due to its lower salt-retention activity. It is a white or almost white, crystalline powder and is available under various brand names such as Cortan, Delta-Dome, Deltasone, Liquid Pred, Meticorten, Orasone, and Paracort.
Uses
1. Used in Anti-Inflammatory Applications:
Prednisone is used as an anti-inflammatory agent for various inflammatory processes. It is particularly effective in reducing inflammation and alleviating symptoms associated with conditions such as rheumatoid arthritis, lupus, and asthma.
2. Used in Allergy Treatment:
Prednisone is used as an anti-allergic medication to treat various allergic reactions, including allergic rhinitis, hives, and allergic conjunctivitis. It helps to suppress the immune system's response to allergens, reducing inflammation and symptoms.
3. Used in Adrenal Gland Insufficiency:
Prednisone is used as a replacement therapy for adrenal gland insufficiency, a condition in which the adrenal glands do not produce enough of the necessary hormones. It helps to restore the balance of hormones in the body and alleviate symptoms.
4. Used in Immunosuppression:
Prednisone is used as an immunosuppressant in various medical conditions, including autoimmune diseases and organ transplants. It helps to suppress the immune system, preventing the body from attacking its own tissues or rejecting a transplanted organ.
5. Used in Downregulating Inflammatory Mediators:
Prednisone is used to downregulate the production of tumor necrosis factor-alpha (TNF-α) and the expression of nuclear factor kappa B (NF-κB), which are key inflammatory mediators involved in the pathogenesis of various diseases. By reducing the levels of these mediators, Prednisone helps to alleviate inflammation and associated symptoms.
Indications
Prednisone 2.5 to 7.5 mg, administered at night or dexamethasone 0.25
to 0.75 mg are useful in female patients, with severe acne unresponsive
to conventional therapy, who suffer from adrenal gland overproduction
of androgens such as congenital adrenal hyperplasia.
Air & Water Reactions
Very slightly water soluble .
Hazard
Questionable carcinogen.
Safety Profile
Poison by
intraperitoneal and subcutaneous routes.
Moderately toxic by intramuscular route.
Human systemic effects: sensory change
involving peripheral nerves, dermatitis.
Experimental reproductive effects.
Questionable carcinogen with experimental
tumorigenic data. Mutation data reported.
Has been implicated in aplastic anemia.
Synthesis
Prednisone is 17α,21-dihydroxypregna-1,4-dien-3,11-20-trione (27.1.31).
Prednisone differs from cortisone in the presence of an additional double bond between C1
and C2. There are various ways of synthesizing it. In one of these, as is in the case when
synthesizing cortisone, it is synthesized from dihydrocortisone acetate. However, in the
given example, this compound undergoes dibromination by molecular bromine, giving
2,4-dibromo-derivative of dihydrocortisone 27.1.30. Dehydrobromination with
3,5-lutidine, followed by subsequent hydrolysis of the acetyl group using potassium bicarbonate
gives the desired prednisone (27.1.31). Prednisone is also synthesized by
microbiological dehydrogenation of cortisone.
Purification Methods
Crystallise prednisone from acetone/hexane, then recrystallise it from Me2CO. The monoacetate crystallises from Me2CO/hexane with m 227-233o(dec), [] D +186o (c 1, dioxane), and the diacetate crystallises from 25Me2CO/hexane with m 219-221o(dec), [] D +125o (c 1, CHCl3). [Hertzog et al. Tetrahedron 18 581 1962, Beilstein 8 IV 3531.]
Check Digit Verification of cas no
The CAS Registry Mumber 53-03-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 3 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 53-03:
(4*5)+(3*3)+(2*0)+(1*3)=32
32 % 10 = 2
So 53-03-2 is a valid CAS Registry Number.
InChI:InChI=1/C21H26O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h5,7,9,14-15,18,22,26H,3-4,6,8,10-11H2,1-2H3/t14?,15?,18?,19-,20-,21-/m0/s1
53-03-2Relevant articles and documents
Biotransformation of cortisone with Rhodococcus rhodnii: Synthesis of new steroids
Bertolasi, Valerio,Buzzi, Raissa,Costa, Stefania,Pedrini, Paola,Semeraro, Bruno,Summa, Daniela,Vertuani, Silvia,Zappaterra, Federico
, (2021)
Cortisone is a steroid widely used as an anti-inflammatory drug able to suppress the immune system, thus reducing inflammation and attendant pain and swelling at the site of an injury. Due to its numerous side effects, especially in prolonged and high-dose therapies, the development of the pharmaceutical industry is currently aimed at finding new compounds with similar activities but with minor or no side effects. Biotransformations are an important methodology towards more sustainable industrial processes, according to the principles of “green chemistry”. In this work, the biotransformation of cortisone with Rhodococcus rhodnii DSM 43960 to give two new steroids, i.e., 1,9β,17,21-tetrahydoxy-4-methyl-19-nor-9β-pregna-1,3,5(10)-trien-11,20-dione and 1,9β,17,20β,21- pentahydoxy-4-methyl-19-nor-9β-pregna-1,3,5(10)-trien-11-one, is reported. These new steroids have been fully characterized.
-
Singh,K. et al.
, p. 513 - 520 (1963)
-
Preparation method of prednisone
-
, (2021/03/05)
The invention discloses a preparation method of prednisone, and belongs to the technical field of preparation and processing of medicines. According to the method, hydrocortisone acetate is used as aninitial raw material, and the prednisone is prepared through three steps of oxidation, biological fermentation dehydrogenation and hydrolysis. According to the preparation method of prednisone, the defects of a traditional process are overcome, the target product is high in purity, good in quality stability, high in yield, low in production cost and mild in reaction condition, a highly toxic cyanide reagent is prevented from being used, and the method is easy and convenient to operate, suitable for industrial production and wide in market prospect.
THERAPEUTIC FOR HEPATIC CANCER
-
, (2011/02/18)
A novel pharmaceutical composition for treating or preventing hepatocellular carcinoma and a method of treatment are provided. A pharmaceutical composition for treating or preventing liver cancer is obtained by combining a chemotherapeutic agent with an anti-glypican 3 antibody. Also disclosed is a pharmaceutical composition for treating or preventing liver cancer which comprises as an active ingredient an anti-glypican 3 antibody for use in combination with a chemotherapeutic agent, or which comprises as an active ingredient a chemotherapeutic agent for use in combination with an anti-glypican 3 antibody. Using the chemotherapeutic agent and the anti-glypican 3 antibody in combination yields better therapeutic effects than using the chemotherapeutic agent alone, and mitigates side effects that arise from liver cancer treatment with the chemotherapeutic agent.