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53-03-2

Basic Information
CAS No.: 53-03-2
Name: Prednisone
Article Data: 51
Molecular Structure:
Molecular Structure of 53-03-2 (Prednisone)
Formula: C21H26O5
Molecular Weight: 358.434
Synonyms: 1,2-Dehydrocortisone;1,4-Pregnadiene-17a,21-diol-3,11,20-trione;1-Dehydrocortisone;17,21-Dihydroxypregn-1,4-diene-3,11,20-trione;17a,21-Dihydroxy-1,4-pregnadiene-3,11,20-trione;Apo-Prednisone;Bicortone;Cartancyl;Colisone;Cortidelt;Dacorten;Decortancyl;Decortin;Dellacort A;Delta-Cortelan;Delta-Dome;Deltacortisone;Deltasone;Deltison;Deltisone;Deltra;Di-Adreson;Pregna-1,4-diene-3,11,20-trione,17,21-dihydroxy-;
EINECS: 200-160-3
Density: 1.3 g/cm3
Melting Point: 236-238 °C(lit.)
Boiling Point: 573.7 °C at 760 mmHg
Flash Point: 314.8 °C
Solubility: 115mg/L(25 oC)
Appearance: white crystalline powder
Hazard Symbols: HarmfulXn,CorrosiveC,FlammableF
Risk Codes: 63-34-11
Safety: 36/37/39-45-26-16
PSA: 91.67000
LogP: 1.76580
Synthetic route
53-06-5

Cortisone

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;
125-10-0

prednisone acetate

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
53-06-5

Cortisone

A

53-03-2

Prednison

B

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%
53-06-5

Cortisone

A

53-03-2

Prednison

B

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%
50-24-8

prednisolon

A

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

53-03-2

Prednison

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

Prednisone pivalate

53-03-2

Prednison

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

Cortisone acetate

53-03-2

Prednison

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

prednisolone 21-acetate

53-03-2

Prednison

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-bromo-acetamide
2: aqueous methanol.KHCO3
View Scheme
28449-43-6

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

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
50-24-8

prednisolon

53-03-2

Prednison

Conditions
ConditionsYield
With oxygen In water; acetonitrile at 24.84℃; Kinetics; Quantum yield; Reagent/catalyst; Photolysis;
Downstream Products
125-10-0
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Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 326.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 ,1981,p. 293.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 26 ,1981,p. 293.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Studies (ipr); No Evidence: mouse CANCAR    Cancer. 40 (1977),1935. ; (ipr); Equivocal Evidence: rat CANCAR    Cancer. 40 (1977),1935. . Reported in EPA TSCA Inventory.

Specification

1. Introduction of Prednisone
Prednisone is a white crystalline powder and an organic compound. The systematic name of this chemical is 17,21-dihydroxypregna-1,4-diene-3,11,20-trione. The product's categories are Antitumors for Research and Experimental Use; Biochemistry; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals; Steroid and Hormone. It is also named as 1,4-Pregnadiene-17a,21-diol-3,11,20-trione. In addition, the Classification Code of Prednisone is Adrenal Cortex Hormones; Anti-Inflammatory Agents; Antineoplastic Agents; Antineoplastic agents, hormonal; Drug / Therapeutic Agent; Glucocorticoid; Glucocorticoids; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Mutation data; Reproductive Effect; Tumor data. Prednisone is practically insoluble in water.

2. Properties of Prednisone
Physical properties about Prednisone are:
(1)ACD/LogP: 1.57; (2)ACD/LogD (pH 5.5): 1.57; (3)ACD/LogD (pH 7.4): 1.57; (4)ACD/BCF (pH 5.5): 9.16; (5)ACD/BCF (pH 7.4): 9.16; (6)ACD/KOC (pH 5.5): 169.92; (7)ACD/KOC (pH 7.4): 169.92; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 69.67 Å2; (12)Index of Refraction: 1.603; (13)Molar Refractivity: 94.08 cm3; (14)Molar Volume: 273.6 cm3; (15)Polarizability: 37.29×10-24cm3; (16)Surface Tension: 58.5 dyne/cm; (17)Density: 1.3 g/cm3; (18)Flash Point: 314.8 °C; (19)Enthalpy of Vaporization: 98.73 kJ/mol; (20)Boiling Point: 573.7 °C at 760 mmHg; (21)Vapour Pressure: 1.51E-15 mmHg at 25°C.

3. Structure Descriptors of Prednisone
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(CO)[C@@]3(O)CC[C@H]2[C@@H]4CC\C1=C\C(=O)\C=C/[C@]1(C)[C@H]4C(=O)C[C@@]23C
(2)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
(3)InChIKey: XOFYZVNMUHMLCC-ZPOLXVRWBN
(4)Std. InChI: InChI=1S/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
(5)Std. InChIKey: XOFYZVNMUHMLCC-ZPOLXVRWSA-N

4. Safety information of Prednisone
The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo oral 400ug/kg (0.4mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Irish Journal of Medical Science. Vol. 155, Pg. 234, 1986.
man TDLo oral 857ug/kg (0.857mg/kg) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE Neurology. Vol. 36, Pg. 729, 1986.
mouse LD50 intramuscular 600mg/kg (600mg/kg)   Cancer Research. Vol. 42, Pg. 122, 1982.
mouse LD50 intraperitoneal 135mg/kg (135mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 101mg/kg (101mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
women TDLo oral 2400ug/kg/2D- (2.4mg/kg) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE Neurology. Vol. 36, Pg. 729, 1986.
women TDLo unreported 113mg/kg (113mg/kg) BLOOD: HEMORRHAGE

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
JAMA, Journal of the American Medical Association. Vol. 243, Pg. 1260, 1980.

5. Safety information of Prednisone
Hazard Codes: Xn,C,F
Risk Statements: 63-34-11
63: Possible risk of harm to the unborn child.
34: Causes burns.
11: Highly Flammable.
Safety Statements: 36/37/39-45-26-16
36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
16: Keep away from sources of ignition - No smoking.
WGK Germany: 3
RTECS: TU4154100
HazardClass: IRRITANT

When you are using this chemical, please be cautious about it as the following:
It is highly flammable and can cause burns. Please keep away from sources of ignition - No smoking. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is possible risk of harm to the unborn child. When you are using it, wear suitable gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

6. Uses of Prednisone
Prednisone can be used to produce androsta-1,4-diene-3,11,17-trione by heating. It will need reagent MnO2 and solvent CHCl3 with reaction time of 4 hours. The yield is about 55.3%.




Besides, it is a white crystalline powder, which should be used in biochemical research. Adrenal cortex hormones drugs, it's anti-inflammatory, anti-allergy and commonly used in chemotherapy, you can improve patient general, and it can be used in acute leukemia and other tumors.

7. Production of Prednisone
Prednisone can be got from CORTISONE.