ChemicalBook Product Catalog API Hormones and the Endocrine System Adrenal corticosteroids Prednisolone-21-acetate

Prednisolone-21-acetate

Product NamePrednisolone-21-acetate
CAS52-21-1
MFC23H30O6
MW402.49
EINECS200-134-1
MOL File52-21-1.mol

Chemical Properties

Melting point	240-244 °C
alpha	D25 +116° (dioxane)
Boiling point	579.8±50.0 °C(Predicted)
Density	1.28±0.1 g/cm3(Predicted)
refractive index	112 ° (C=1, Dioxane)
storage temp.	2-8°C
solubility	Practically insoluble in water, slightly soluble in ethanol (96 per cent) and in methylene chloride.
form	Solid
pka	12.41±0.70(Predicted)
color	White to Off-White
Water Solubility	11.6mg/L(25 ºC)
Merck	7721
BRN	3111798
Stability	Stable. Incompatible with strong oxidizing agents.
Major Application	pharmaceutical (small molecule)
InChIKey	LRJOMUJRLNCICJ-JZYPGELDSA-N
SMILES	[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)[C@@]1([H])[C@@H](O)C[C@@]4(C)[C@@]2([H])CC[C@]4(O)C(=O)COC(C)=O
CAS DataBase Reference	52-21-1(CAS DataBase Reference)
NIST Chemistry Reference	1,4-Pregnadiene-3,20-dione, 11beta,17alpha,21-trihydroxy-, acetate(52-21-1)

Safety Information

Hazard Codes	N
Risk Statements	25-34-11
Safety Statements	45-36/37/39-26-16
WGK Germany	3
RTECS	TU4152500
HS Code	29372900
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Repr. 1B

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Chemical Properties

White or almost white, crystalline powder.

Originator

Sterane, Phipharmex ,US ,1955

Uses

glucocorticoid

Uses

Synthetic corticosteroid; metabolically interconvertible with prednisone.

Definition

ChEBI: Prednisolone acetate is a corticosteroid hormone.

Manufacturing Process

To a solution of 0.85 gram of 1,4-pregnadiene-11β,17α,21-triol-3,20-dione (prednisolone) in 5 ml of pyridine are added 3 ml of acetic anhydride. The reaction mixture is allowed to stand at room temperature overnight and is then diluted with ice water. The resulting precipitate is filtered from the mixture and recrystallized from acetone-hexane. There is recovered 0.45 gram of 1,4-pregnadiene-11β,17α,21-triol-3,20-dione 21-acetate, MP 235°239°C. On recrystallization, the MP rose to 237°-239°C.

brand name

Econopred (Alcon); Meticortelone (Schering); Omnipred (Alcon); Sterane (Pfizer).

Therapeutic Function

Glucocorticoid

Biological Activity

Prednisolone Acetate (Omnipred) is a synthetic corticosteroid that is a particularly potent immunosuppressant.

Clinical Use

For rheumatoid arthritis, rheumatic fever, lupus erythematosus, scleroderma, dermatomyositis, acute lymphoblastic leukemia, etc.

Purification Methods

Recrystallise prednisolone acetate from EtOH, Me2CO, Me2CO/hexane, and it has UV with max at 243nm in EtOH. [Joly et al. Bull Soc Chim Fr 366 1958; Herzog et al. J Am Chem Soc 77 4781 1955, Beilstein 8 IV 3468.]

References

[1] Patent: CN105503986, 2016, A. Location in patent: Paragraph 0027; 0028

Preparation Products And Raw materials