104286-02-4

Usage

Uses

A metabolite of Prednicarbate (P703700).

InChI:InChI=1/C24H32O7/c1-4-30-21(29)31-24(19(28)13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)20(16)18(27)12-23(17,24)3/h7,9,11,16-18,20,25,27H,4-6,8,10,12-13H2,1-3H3/t16-,17-,18-,20+,22-,23-,24-/m0/s1

Upstream product

• 73771-04-7 prednicarbate 
• 26129-79-3 prednisolone-17,21-diethylorthocarbonate 
• 50-24-8 prednisolon 

Downstream Products

• 73771-04-7 prednicarbate 
• 928623-80-7 (11β)-17-[(ethoxycarbonyl)oxy]-11-hydroxy-21-[1-oxo-[3-(chloromethyl)benzoxy]]pregna-1,4-diene-3,20-dione 

Relevant academic research and scientific papers

Method for preparing prednicarbate intermediate

The invention relates to a method for preparing a prednicarbate key intermediate (a compound of a formula III shown in the description). According to the method, a compound of a formula II shown in the description is adopted as a raw material, water and ethanol are adopted as solvents, and the compound of the formula III shown in the description is prepared through a hydrolysis reaction under theacid condition. Compared with the prior art, the conversion rate of the compound of the formula II shown in the description is increased, problems that the compound of the formula III shown in the description is not easy to separate, purify, crystallize and the like can be solved, the compound of the formula III with high purity can be conveniently and rapidly prepared, and the method is applicable to industrial production.

Microbial transformation of topical corticosteroid: Prednicarbate

In the present research, the steroidal antiinflammatory topically used drug prednicarbate (1) was subjected to microbial biotransformation by Cunninghamella elegans. Prednicarbate (1) was transformed into various metabolites. One new and two known metabolites were purified named as prednisolone 17-ethylcarbonate (2) Prednisolone (3) and 4-(4-hydroxybenzyl)-2-(3-methylbut-2-enyl)phenyl methyl carbonate (4). The compound (4) was separated as a new compound and was not reported in literature. Its structure did not show resemblance with prednicarbate so possibly derived from fungal mass. Their structures were elucidated by using modern spectroscopic techniques e.g. 13C NMR, 1H NMR, HMQC, HMQC, COSY, NOESY and mass spectrometry e.g. EI-MS.

Investigation on the Photostability of Halometasone and Prednicarbate in the Crystal State and Crystal Structure of Halometasone

UV irradiation of halometasone (1) in the crystal state yields three photoproducts: 2-chloro-6α,9-difluoro-11β,17α-dihydroxy-16-α-methyl-3-oxoandrosta-1,4-diene-17β-carbaldehyde (3), 2-chloro-6α,9-difluoro-11β-hydroxy-16α-methylandrosta-1,4-diene-3,17-dione (4) and the dimerization product 2ξ-chloro-2ξ-(2-chloro-6α,9-difluoro-11β,21ξ-trihydroxy-16α-methyl-3,20-dioxopregna-1,4-dien-21-yl)-6α,9-difluoro-11β,17,21-trihydroxy-16α-methylpregna-4-ene-3,20-dione (5).The structure of 5 is determined by the molecular packing of 1 in the crystal, as shown by an X-ray analysis of 1.Two photoproducts are formed after irradiation of prednicarbate (2): 11β,17-dihydroxy-21-propionyloxypregna-1,4-diene-3,20-dione (6) and 17-(ethoxycarbonyloxy)-11β,21-dihydroxypregna-1,4-diene-3,20-dione (7). Key Words: Prednicarbate / Halometasone / Photochemistry

Synthesis of prednicarbate, an unhalogenated topical antiinflammatory derivative of prednisolone-17-ethylcarbonate-21-propionate

The synthesis of prednisolone-17-ethylcarbonate-21-propio-nate (prednicarbate, Hoe 777) passing the intermediate products prednisolone 17,12-diethylorthocarbonate and prednisolone-17-ethylcarbonate as well as some physico-chemical properties and spectroscopic data of especially the 1H-NMR- and MS-spectrum, are reported. Prednicarbate has an optimal split of topical/systemic antiinflammatory activity.