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53-03-2

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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

53-03-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name prednisone

1.2 Other means of identification

Product number -
Other names Wojtab

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:53-03-2 SDS

53-03-2Synthetic route

Cortisone
53-06-5

Cortisone

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
With Rhodococcus coprophilus DSM 43347 In dimethyl sulfoxide at 30℃; for 24h; Reagent/catalyst; Green chemistry; regiospecific reaction;94%
With selenium(IV) oxide
mit Hilfe von Didymella lycopersici;
mit Hilfe von Corynebacterium simplex;
mit Hilfe von Corynebacterium simplex;
prednisone acetate
125-10-0

prednisone acetate

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
With di(n-butyl)tin oxide In methanol for 4h; Heating;89%
Stage #1: prednisone acetate With potassium carbonate In ethanol; water at 15℃;
Stage #2: With acetic acid In ethanol; water Solvent; Reagent/catalyst; Temperature;
68.5%
With potassium hydrogencarbonate
With potassium hydroxide
With sodium methylate
Cortisone
53-06-5

Cortisone

A

Prednison
53-03-2

Prednison

B

17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione

17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione

Conditions
ConditionsYield
With Rhodococcus baikonurensis DSM 44587 In dimethyl sulfoxide at 30℃; for 72h; Reagent/catalyst; Green chemistry; regiospecific reaction;A 27%
B 68%
Cortisone
53-06-5

Cortisone

A

Prednison
53-03-2

Prednison

B

17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione
600-92-0

17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione

Conditions
ConditionsYield
With Rhodococcus rhodnii DSM 43960 In dimethyl sulfoxide for 24h; Green chemistry; Enzymatic reaction;A 30%
B 10%
prednisolon
50-24-8

prednisolon

A

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
898-84-0

(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-6H-cyclopenta[a]phenanthrene-3,17-dione

B

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
Product distribution; Rate constant; Irradiation; radiolytic degradation;
Prednisone pivalate
51192-49-5

Prednisone pivalate

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
With Curvularia tuberculata In water at 30℃; for 72h; Yield given;
Cortisone acetate
50-04-4

Cortisone acetate

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SeO2
2: methanol.KOH
View Scheme
prednisolone 21-acetate
52-21-1

prednisolone 21-acetate

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-bromo-acetamide
2: aqueous methanol.KHCO3
View Scheme
21-acetoxy-11β-hydroxy-pregna-1,4,17(20)c-trien-3-one
28449-43-6

21-acetoxy-11β-hydroxy-pregna-1,4,17(20)c-trien-3-one

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: diacetoxyiodanyl-benzene
2: N-bromo-acetamide
3: aqueous methanol.KHCO3
View Scheme
prednisolon
50-24-8

prednisolon

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
With oxygen In water; acetonitrile at 24.84℃; Kinetics; Quantum yield; Reagent/catalyst; Photolysis;
hydrocortisone acetate
50-03-3

hydrocortisone acetate

Prednison
53-03-2

Prednison

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; manganese(ll) chloride; chromium(VI) oxide / water; chloroform / 30 °C
2: Arthrobacter simplex By-2-13
3: potassium carbonate / water; ethanol / 15 °C
View Scheme
Prednison
53-03-2

Prednison

acetic anhydride
108-24-7

acetic anhydride

17α,21-diacetoxypregna-1,4-diene-3,11,20-trione
6677-19-6

17α,21-diacetoxypregna-1,4-diene-3,11,20-trione

Conditions
ConditionsYield
With pyridine at 85 - 90℃; for 2.5h; Reagent/catalyst; Temperature;98.4%
Prednison
53-03-2

Prednison

Cortisone
53-06-5

Cortisone

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrazine hydrate In methanol at 62 - 64℃; for 8h;98%
Prednison
53-03-2

Prednison

4-Nitrophenyl chloroformate
7693-46-1

4-Nitrophenyl chloroformate

prednisone
1092578-27-2

prednisone

Conditions
ConditionsYield
With dmap In dichloromethane at 0℃;95%
Stage #1: Prednison; 4-Nitrophenyl chloroformate In chloroform at 0℃; for 1.25h;
Stage #2: With pyridine In chloroform
Prednison
53-03-2

Prednison

androsta-1,4-diene-3,11,17-trione
7738-93-4

androsta-1,4-diene-3,11,17-trione

Conditions
ConditionsYield
In water; acetonitrile at 20℃; Electrochemical reaction;89%
With manganese(IV) oxide In chloroform for 4h; Heating;55.3%
Product distribution; Rate constant; Irradiation; radiolytic degradation;
Multi-step reaction with 2 steps
1: borane-THF / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere
2: sodium periodate / tetrahydrofuran; water; acetone / 3.08 h / 0 - 23 °C / Inert atmosphere
View Scheme
Prednison
53-03-2

Prednison

((8S,9S,10R,13S,14S,17R)-17-Hydroxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-oxo-acetaldehyde

((8S,9S,10R,13S,14S,17R)-17-Hydroxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-oxo-acetaldehyde

Conditions
ConditionsYield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 24h; Ambient temperature;86%
Prednison
53-03-2

Prednison

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

17-hydroxy-21-methanesulfonyloxy-pregna-1,4-diene-3,11,20-trione
76676-23-8

17-hydroxy-21-methanesulfonyloxy-pregna-1,4-diene-3,11,20-trione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;86%
Prednison
53-03-2

Prednison

2-phenethyl-1,1,3,3-tetramethylisothiouronium salt

2-phenethyl-1,1,3,3-tetramethylisothiouronium salt

C29H34O4S

C29H34O4S

Conditions
ConditionsYield
With N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In chloroform at 20℃; for 2h;86%
Prednison
53-03-2

Prednison

17α-hydroxy-11-oxoandrosta-1,4-dien-3-one-17β-carboxylic acid
78261-67-3

17α-hydroxy-11-oxoandrosta-1,4-dien-3-one-17β-carboxylic acid

Conditions
ConditionsYield
With sodium periodate In tetrahydrofuran; methanol at 20℃; for 2h;84%
Prednison
53-03-2

Prednison

ethylenediamine
107-15-3

ethylenediamine

C27H44N6O2
1522230-44-9

C27H44N6O2

Conditions
ConditionsYield
With boric acid In ethanol at 20℃; for 72h;80%
formaldehyd
50-00-0

formaldehyd

Prednison
53-03-2

Prednison

prednisone-BMD
26341-55-9

prednisone-BMD

Conditions
ConditionsYield
With hydrogenchloride In chloroform for 16h; Ambient temperature;77%
Prednison
53-03-2

Prednison

17-hydroxypregna-1,4-diene-3,11,20-trione
1242-49-5

17-hydroxypregna-1,4-diene-3,11,20-trione

Conditions
ConditionsYield
With pyridine; iodine; triphenylphosphine In toluene for 6h; Inert atmosphere; Reflux; chemoselective reaction;76%
formaldehyd
50-00-0

formaldehyd

Prednison
53-03-2

Prednison

(20R)-17,20:20,21-bis[methylenebis(oxy)]pregna-1,4-diene-3,11-dione
67254-01-7

(20R)-17,20:20,21-bis[methylenebis(oxy)]pregna-1,4-diene-3,11-dione

Conditions
ConditionsYield
With hydrogenchloride In chloroform; water73.3%
oleyl hemisuccinate
20060-41-7

oleyl hemisuccinate

Prednison
53-03-2

Prednison

oleyl 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethylsuccinate

oleyl 2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethylsuccinate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 14h; Inert atmosphere;71%
Prednison
53-03-2

Prednison

17-hydroxy-21-phosphonooxy-pregna-1,4-diene-3,11,20-trione
57099-40-8

17-hydroxy-21-phosphonooxy-pregna-1,4-diene-3,11,20-trione

Conditions
ConditionsYield
With pyridine; 2-cyanoethyl phosphate; dicyclohexyl-carbodiimide70%
Prednison
53-03-2

Prednison

bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride
117835-14-0

bicyclo[2.2.1]hept-5-ene-2-carbonyl chloride

C29H34O6
1119900-18-3

C29H34O6

Conditions
ConditionsYield
With pyridine at 20℃; for 0.5h; Molecular sieve; Inert atmosphere;60%
Prednison
53-03-2

Prednison

21-hydroxy-1,4-pregnadiene-3,11,20-trione
67067-81-6

21-hydroxy-1,4-pregnadiene-3,11,20-trione

Conditions
ConditionsYield
With trimethylsilyl iodide In acetonitrile for 4h; Ambient temperature;54%
With trimethylsilyl iodide; sodium sulfite In hexane; chloroform; ethyl acetate; acetonitrile
Prednison
53-03-2

Prednison

A

20-hydroxy-3,11-dioxo-1,4,trans-17(20)-pregnatrien-21-al
118724-36-0

20-hydroxy-3,11-dioxo-1,4,trans-17(20)-pregnatrien-21-al

B

20-hydroxy-3,11-dioxo-1,4,cis-17(20)-pregnatrien-21-al
118724-35-9

20-hydroxy-3,11-dioxo-1,4,cis-17(20)-pregnatrien-21-al

Conditions
ConditionsYield
With zinc diacetate; acetic acid Heating;A 5.1%
B 42.2%
Prednison
53-03-2

Prednison

sodium 2-(4-methylpiperazin-1-yl)acetate

sodium 2-(4-methylpiperazin-1-yl)acetate

C28H38N2O6

C28H38N2O6

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide In acetonitrile at 20℃; for 18h;38%
Prednison
53-03-2

Prednison

sodium 4-(4-methylpiperazin-1-yl)butanoate

sodium 4-(4-methylpiperazin-1-yl)butanoate

C30H42N2O6

C30H42N2O6

Conditions
ConditionsYield
With 2-chloro-1-methyl-pyridinium iodide In acetonitrile at 20℃; for 18h;36%
Prednison
53-03-2

Prednison

phenyl(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside)
225242-73-9

phenyl(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside)

17α-hydroxy-3,11,20-trioxo-pregnadien-(1,4)-yl-(21)-2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside
1092578-16-9

17α-hydroxy-3,11,20-trioxo-pregnadien-(1,4)-yl-(21)-2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranoside

Conditions
ConditionsYield
With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In chloroform at 0℃; Molecular sieve;26%
phenyl-4-O-(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl)-2-trifluoracetamido-2-deoxy-3,6-di-O-acetyl-1-thio-D-glucopyranoside
1092578-22-7

phenyl-4-O-(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranosyl)-2-trifluoracetamido-2-deoxy-3,6-di-O-acetyl-1-thio-D-glucopyranoside

Prednison
53-03-2

Prednison

17α-hydroxy-3,11,20-trioxo-pregnadien-(1,4)-yl-(21)-4-O-(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-2-trifluoracetamido-2-deoxy-3,6-di-O-acetyl-β-D-glucopyranose
1092578-23-8

17α-hydroxy-3,11,20-trioxo-pregnadien-(1,4)-yl-(21)-4-O-(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-2-trifluoracetamido-2-deoxy-3,6-di-O-acetyl-β-D-glucopyranose

Conditions
ConditionsYield
With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate In chloroform at 0℃; Molecular sieve;26%
Prednison
53-03-2

Prednison

semicarbazide hydrochloride
563-41-7

semicarbazide hydrochloride

17,21-dihydroxy-pregna-1,4-diene-3,11,20-trione-3,20-disemicarbazone
113927-06-3

17,21-dihydroxy-pregna-1,4-diene-3,11,20-trione-3,20-disemicarbazone

Prednison
53-03-2

Prednison

20β-dihydroprednisone
600-93-1

20β-dihydroprednisone

Conditions
ConditionsYield
With Rhodotorula longissima
Prednison
53-03-2

Prednison

17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione
600-92-0

17α,20β,21-trihydroxy-1,4-pregnadiene-3,11-dione

Conditions
ConditionsYield
With sodium tetrahydroborate
With calonectria decora
With streptomyces griseus
With streptomyces hydrogenating agents
Prednison
53-03-2

Prednison

pivaloyl chloride
3282-30-2

pivaloyl chloride

Prednisone pivalate
51192-49-5

Prednisone pivalate

Conditions
ConditionsYield
With pyridine; chloroform
Prednison
53-03-2

Prednison

propionic acid anhydride
123-62-6

propionic acid anhydride

17-hydroxy-21-propionyloxy-pregna-1,4-diene-3,11,20-trione
115322-27-5

17-hydroxy-21-propionyloxy-pregna-1,4-diene-3,11,20-trione

Conditions
ConditionsYield
With pyridine

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.

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