73771-04-7

Usage

Uses

Used in Pharmaceutical Industry:
[2-(17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl] propanoate is used as a pharmaceutical agent for its anti-inflammatory properties. It is particularly effective in treating cutaneous inflammatory disorders such as eczema and psoriasis due to its potent topical anti-inflammatory activity and minimal systemic effects.
Used in Topical Corticosteroid Formulations:
In the field of dermatology, [2-(17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl] propanoate is used as a glucocorticoid in topical formulations. It exhibits anti-inflammatory activity comparable to other corticosteroids when administered topically, making it a valuable component in treatments for various skin conditions.
Used in Wound Healing Applications:
[2-(17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl] propanoate is also utilized in wound healing processes. Topical administration of [2-(17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl] propanoate has been shown to induce wound healing in hairless mice, suggesting its potential use in accelerating the healing of various skin injuries and conditions.

Indications

Prednicarbate (Dermatop E) is a synthetic nonfluorinated topical corticosteroid.

InChI:InChI=1/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3/t18-,19-,20-,23+,25-,26-,27-/m0/s1

Synthetic route

Prednisolone 17-ethylcarbonate (104286-02-4) + propionic acid anhydride (123-62-6) → prednicarbate (73771-04-7)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 24h;	87.1%
With dmap In dichloromethane at 20℃; for 16h;	30.4%

propionyl chloride (79-03-8) + Prednisolone 17-ethylcarbonate (104286-02-4) → prednicarbate (73771-04-7)

Conditions	Yield
With pyridine 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h; Yield given;

prednisolon (50-24-8) + HgO → prednicarbate (73771-04-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / p-TosOH / dioxane / 17 h / 22 °C 2: glacial AcOH, H2O / 5 h / 18 °C 3: pyridine / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme
Multi-step reaction with 3 steps 1: 90 percent / p-TosOH / dioxane / 17 h / 22 °C 2: glacial AcOH, H2O / 5 h / 18 °C 3: 30.4 percent / 4-dimethylaminopyridine / CH2Cl2 / 16 h / 20 °C View Scheme

prednisolone-17,21-diethylorthocarbonate (26129-79-3) → prednicarbate (73771-04-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: glacial AcOH, H2O / 5 h / 18 °C 2: pyridine / 1.) 0 deg C, 30 min, 2.) 20 deg C, 2 h View Scheme
Multi-step reaction with 2 steps 1: glacial AcOH, H2O / 5 h / 18 °C 2: 30.4 percent / 4-dimethylaminopyridine / CH2Cl2 / 16 h / 20 °C View Scheme

prednicarbate (73771-04-7) → 11β,17-dihydroxy-21-propionyloxypregna-1,4-diene-3,20-dione (5740-62-5) + Prednisolone 17-ethylcarbonate (104286-02-4)

Conditions	Yield
With silica gel for 20h; Irradiation;	A 0.62% B 0.58%

prednicarbate (73771-04-7) → C24H30O5 (50802-85-2)

Conditions	Yield
at 264℃; for 0.5h; Inert atmosphere;

prednicarbate (73771-04-7) → prednisolon (50-24-8) + 4-(4-hydroxybenzyl)-2-(3-methylbut-2-enyl)phenyl methyl carbonate + Prednisolone 17-ethylcarbonate (104286-02-4)

Conditions	Yield
With water In acetone at 25 - 28℃; for 336h; Microbiological reaction;

Upstream product

• 79-03-8 propionyl chloride 
• 104286-02-4 Prednisolone 17-ethylcarbonate 
• 123-62-6 propionic acid anhydride 
• 50-24-8 prednisolon 
• 26129-79-3 prednisolone-17,21-diethylorthocarbonate 

Downstream Products

• 5740-62-5 11β,17-dihydroxy-21-propionyloxypregna-1,4-diene-3,20-dione 
• 104286-02-4 Prednisolone 17-ethylcarbonate 
• 50-24-8 prednisolon 

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.

Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor

Methods for reducing or preventing transplant rejection in the eye of an individual are described, comprising: a) performing an ocular transplant procedure; and b) implanting in the eye a bioerodible drug delivery system comprising an immunosuppressive agent and a bioerodible polymer.

Composition for the topical treatment of poison ivy and other forms of contact dermatitis

Composition for topical administration comprising (a) a corticosteroid, and (b) a drying agent.

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.