53-03-2 Usage
Chemical Properties
White or almost white, crystalline powder.
Uses
Different sources of media describe the Uses of 53-03-2 differently. You can refer to the following data:
1. Adrenocortical steroid. Glucocorticoid, antiinflammatory.
2. Downregulates TNF-α production and NF-κB expression
3. Prednisone is used for the same indications as cortisone for inflammatory processes,
allergies, and adrenal gland insufficiency; however, it is somewhat more active than cortisone
and has less of an effect on mineral volume.
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.
Definition
ChEBI: A synthetic glucocorticoid drug that is particularly effective as an immunosuppressant, and affects virtually all of the immune system. Prednisone is a prodrug that is converted by the liver into prednisolone (a beta-hydroxy group instead
f the oxo group at position 11), which is the active drug and also a steroid.
Brand name
Cortan (Halsey); Delta-Dome (Bayer); Deltasone (Pharmacia & Upjohn); Liquid Pred (Muro); Meticorten (Schering); Orasone (Solvay Pharmaceuticals); Paracort (Parke-Davis).
General Description
Prednisone, Δ1-cortisone, 17,21-dihydroxypregna-1,4-diene-3,11,20-trione, has systemic activityvery similar to that of prednisolone, and because of itslower salt-retention activity, it is often preferred over cortisoneor hydrocortisone. Prednisone must be reduced in vivoto prednisolone to provide the active GC.
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)
-
Δ1-dehydrogenation and C20 reduction of cortisone and hydrocortisone catalyzed by rhodococcus strains
Costa, Stefania,Fantin, Giancarlo,Semeraro, Bruno,Summa, Daniela,Zappaterra, Federico
, (2020/05/25)
Prednisone and prednisolone are steroids widely used as anti-inflammatory drugs. Development of the pharmaceutical industry is currently aimed at introducing biotechnological processes and replacing multiple-stage chemical syntheses. In this work we evaluated the ability of bacteria belonging to the Rhodococcus genus to biotransform substrates, such as cortisone and hydrocortisone, to obtain prednisone and prednisolone, respectively. These products are of great interest from a pharmaceutical point of view as they have higher anti-inflammatory activity than the starting substrates. After an initial lab-scale screening of 13 Rhodococcus strains, to select the highest producers of prednisone and prednisolone, we reported the 200 ml-batch scale-up to test the process efficiency and productivity of the most promising Rhodococcus strains. R. ruber, R. globerulus and R. coprophilus gave the Δ1-dehydrogenation products of cortisone and hydrocortisone (prednisone and prednisolone) in variable amounts. In these biotransformations, the formation of products with the reduced carbonyl group in position C20 of the lateral chain of the steroid nucleus was also observed (i.e., 20β-hydroxy-prednisone and 20β-hydroxy-prednisolone). The yields, the absence of collateral products, and in some cases the absence of starting products allow us to say that cortisone and hydrocortisone are partly degraded.
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.
