62358-12-7

Basic information

• Product Name: 20-dihydroprednisolonic acid
• Synonyms: 20-dihydroprednisolonic acid
• CAS NO: 62358-12-7
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.4434
• Mol File: 62358-12-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 623°Cat760mmHg
• Flash Point: 344.6°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 3.92E-18mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Dioxane (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 20-dihydroprednisolonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 20-dihydroprednisolonic acid(62358-12-7)
• EPA Substance Registry System: 20-dihydroprednisolonic acid(62358-12-7)

Safety Data

• Hazardous Substances Data: 62358-12-7(Hazardous Substances Data)

Usage

Description

20-Dihydroprednisolonic acid is a derivative of Prednisolone, a glucocorticosteroid that possesses anti-inflammatory and immunosuppressive properties. It is primarily used in the medical field for the treatment of various conditions, including chronic obstructive pulmonary disease (COPD).

Uses

Used in Pharmaceutical Industry:
20-Dihydroprednisolonic acid is used as a therapeutic agent for the treatment of chronic obstructive pulmonary disease (COPD). It helps in reducing inflammation and managing the symptoms associated with the disease, thereby improving the patient's quality of life.
Used in Medical Treatment:
20-Dihydroprednisolonic acid is used as an anti-inflammatory and immunosuppressive agent in the treatment of various medical conditions. Its glucocorticosteroid properties make it effective in managing inflammation and suppressing the immune system, which can be beneficial for patients with autoimmune disorders or those undergoing organ transplants.

InChI:InChI=1/C21H28O6/c1-19-7-5-12(22)9-11(19)3-4-13-14-6-8-21(27,17(24)18(25)26)20(14,2)10-15(23)16(13)19/h5,7,9,13-17,23-24,27H,3-4,6,8,10H2,1-2H3,(H,25,26)/t13-,14-,15-,16+,17?,19-,20-,21-/m0/s1

Upstream product

• 97232-42-3 methyl 11β,17α,20α-trihydroxy-3-oxo-1,4-pregnadiene-21-oate 
• 50-24-8 prednisolon 

Downstream Products

• 97142-19-3 methyl 17,20α-acetonidodihydroprednisolonate 

Relevant articles and documents

Effect of chirality at C-20 of methyl 11β,17α,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate derivatives on antiinflammatory activity

In an effort to determine the C-20 chirality effect on the antiinflammatory activity of 17β-glycolate esters, methyl 11β,17α,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate and its 9α-fluoro analog, their acetonide and their carbonate derivatives were synthesized and evaluated. The agents were tested for their binding potency to the macrophage glucocorticoid receptor, and their effect on LPS-induced nitric oxide generation in RAW 264.7 cells. The acetonide derivatives showed the highest binding affinity while the triols and carbonates bound rather poorly to the receptors. With the exception of the triols, the α-isomer in each pair of the agents exhibited higher binding affinity to the receptor than its corresponding β-isomer, clearly indicating that C-20 chirality has a significant effect on antiinflammatory activity. In addition, the α-isomers of the acetonides showed substantially higher binding affinity than the parent compound, prednisolone. In contrast to the high binding activity exhibited by some of the acetonides, all of the agents showed weak inhibitory effect on NO generation. Metabolic inactivation during assessment of NO inhibition may play a role in the divergence noted between receptor affinity and the measured biologic activity resulting from the binding.

Anti-inflammatory prednisolone steroids

Derivatives of prednisolone of the formula STR1 wherein CR1 is C=O, α-HCOH, β-HCOH, or a mixture of α-HCOH and β-HCOH CR2 is HC(OH) OR6 or HCO when CR1 is C=O; CR2 is COOR3 or CONHR4 when CR1 is α-HCOH, β-HCOH, or a mixture of α-HCOH and β-HCOH: R3 is alkyl of 1-5 carbon atoms; R4 is alkyl of 1-5 carbon atoms, benzyl, or phenethyl; R5 is hydrogen, acetyl, or benzoyl; R6 is alkyl of 1-5 carbon atoms; R7 is α- or β-position of hydrogen, hydroxyl, methyl, acetate esters of 1-5 carbon atoms, or alkoxy of 1-5 carbon atoms; and X and Y are hydrogen, halogen or methyl; and process for preparing these compounds. The compounds are useful as anti-inflammatory agents which have reduced side effects.

Prednisolone derivatives

Novel prednisolone derivatives modified at C-17,C-20 and/or C-21 positions. Many of the compounds are anti-inflammatory agents which do not significantly suppress the pituitary-adrenal axis.