111802-43-8

Basic information

• Product Name: methyl 11,21-dihydroxy-3,20-dioxopregna-1,4-diene-16-carboxylate
• CAS NO: 111802-43-8
• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.4807
• Mol File: 111802-43-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 574.2°C at 760 mmHg
• Flash Point: 196.1°C
• Density: 1.28g/cm³
• Vapor Pressure: 1.41E-15mmHg at 25°C
• Refractive Index: 1.584
• CAS DataBase Reference: methyl 11,21-dihydroxy-3,20-dioxopregna-1,4-diene-16-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 11,21-dihydroxy-3,20-dioxopregna-1,4-diene-16-carboxylate(111802-43-8)
• EPA Substance Registry System: methyl 11,21-dihydroxy-3,20-dioxopregna-1,4-diene-16-carboxylate(111802-43-8)

Safety Data

• Hazardous Substances Data: 111802-43-8(Hazardous Substances Data)

Upstream product

• 137759-51-4 C₂₅H₃₄O₆ 
• 52628-64-5 prednisolone Acetate 
• 17652-24-3 prednisolone 17,21-diacetate 
• 3044-42-6 21-acetoxy-11β-hydroxyl-1,4,16-pregnatriene-3,20-dione 
• 50-24-8 prednisolon 
• 67-56-1 methanol 
• 119465-19-9 11β,21-dihydroxy-3,20-dioxo-1,4-pregnadiene-16α-carboxylic acid 
• 111802-39-2 21-acetoxy-16α-cyano-11β,21-dihydroxy-3,20-dioxo-1,4-pregna-diene 

Relevant articles and documents

Steroidal anti-inflammatory antedrugs: Synthesis and pharmacological evaluation of 16&α-alkoxycarbonyl-17-deoxyprednisolone derivatives

In a continuing effort to minimize the systemic adverse effects of potent anti-inflammatory steroids, a series of 16α-alkoxycarbonyl-17-deoxyprednisolone derivatives: methyl (8a), ethyl (8b), isopropyl (8c), and benzyl (8d) 11β,21-dihydroxy-3,20-dioxo-1,4-pregnadiene-16α-carboxylate, was synthesized and evaluated for their topical and local anti-inflammatory activities.In the acute croton oil-induced ear edema dose-response bioassay, the topical and anti-inflammatory potencies of these esters relative to prednisolone, 1, were: 8a: 1.0, 8b: 1.3, 8c: 4.0, 8d: 4.7 and 1: 1.0.The putative metabolite, 11β,21-dihydroxy-3,20-dioxo-1,4-pregnadiene-16α-carboxylic acid, 7, was inactive in this test.A seven day cotton pellet granuloma bioassay was employed to study the local and systemic anti-inflammatory activities of these steroids.The local anti-inflammatory potencies of these esters relative to prednisolone, 1, were 1.3, 1.5, 2.3, 2.5, and 1.0 for 8a, 8b, 8c, 8d, and 1, respectively.In this semi-chronic study, only prednisolone exhibited significant untoward side effects, such as reduction in thymus weights, normal body weight gain, and normal plasma corticosterone levels.The increase in the topical and local potencies of these steroid esters was consistent with the increase in their 1-octanol/buffer partition coefficient.The ratio of local to systemic anti-inflammatory activity of 8c and 8d was four times that of prednisolone.The effects of increasing the size of the alkoxy group of these new steroids on both topical and local anti-inflammatory activity and their concomitant decrease in untoward systemic effects were unequivocally demonstrated.The reduction of the adverse systemic effects is attributed to the presence of the metabolically labile 16-carboxy ester moiety which is metabolized into the inactive steroid acid upon entry into the systemic circulation (antedrug concept). - Keywords: 16α-alkoxycarbonyl-17-deoxyprednisolone derivatives, anti-inflammatory steroids, antedrug, croton oil-induced ear edema assay, cotton pellet granuloma bioassay