73771-04-7

Basic information

• Product Name: [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
• Synonyms: PREDNICARBATE;[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;11β，17，21-Trihydroxypregna-1，4-diene-3，20-dione 17-(ethylcarbonate)-21-propionate;Dermatop;HOE-777;Prednitop;Regemt;S-77-0777
• CAS NO: 73771-04-7
• Molecular Formula: C₂₇H₃₆O₈
• Molecular Weight: 488.57
• EINECS: 277-590-3
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 73771-04-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 110-112°; mp 183°
• Boiling Point: 640.7 °C at 760 mmHg
• Flash Point: 209.4 °C
• Appearance: /
• Density: 1.25 g/cm³
• Vapor Pressure: 4.11E-19mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Refrigerator
• Solubility: Practically insoluble in water, freely soluble in acetone and in ethanol (96 per cent), sparingly soluble in propylene glycol. It shows polymorphism (5.9).
• PKA: 14.05±0.70(Predicted)
• CAS DataBase Reference: [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(CAS DataBase Reference)
• NIST Chemistry Reference: [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(73771-04-7)
• EPA Substance Registry System: [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(73771-04-7)

Safety Data

• Hazardous Substances Data: 73771-04-7(Hazardous Substances Data)

Usage

Description

Different sources of media describe the Description of 73771-04-7 differently. You can refer to the following data:
1. Prednicarbate is a potent topical antiinflammatory agent with minimal systemic effects. It is useful in the treatment of cutaneous inflammatory disorders such as eczema and psoriasis.
2. Prednicarbate is a synthetic corticosteroid and a derivative of prednisolone . It has anti-inflammatory activity comparable to that of desoximetasone in various murine models when administered topically but lacks activity when administered subcutaneously. Topical administration of prednicarbate (2 drops of a 0.1% solution per day) induces wound healing in hairless mice. Formulations containing prednicarbate have been used to treat chronic hand eczema.

Chemical Properties

White or almost white, crystalline powder.

Uses

Topical anti-inflammatory agent. Glucocorticoid. Prednicarbate (Dermatop E) is a synthetic nonfluorinated topical corticosteroid.

Indications

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

Brand name

Dermatop (Sanofi Aventis).

General Description

Prednicarbate, 17-[(ethoxycarbonyl)oxy]-11β-hydroxy-21-(1-oxopropoxy)pregna-1,4-diene-3,20-dione, is a prednisolone derivative with a C21 propionateester and a C17 ethyl carbonate group. It is availablefor use only in a 0.1% topical cream. Prednicarbate is amedium-potency GC.

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

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

Downstream Products

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

Relevant articles and documents

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.

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.