Prednicarbate

Base Information

• Chemical Name: Prednicarbate
• CAS No.: 73771-04-7
• Molecular Formula: C27H36O8
• Molecular Weight: 488.578
• Hs Code.: 2937290000
• European Community (EC) Number: 277-590-3
• UNII: V901LV1K7D
• DSSTox Substance ID: DTXSID9045502
• Nikkaji Number: J12.640C
• Wikipedia: Prednicarbate
• Wikidata: Q4376623
• NCI Thesaurus Code: C47684
• RXCUI: 34369
• Pharos Ligand ID: 55FY9TY2KF9H
• Metabolomics Workbench ID: 145852
• ChEMBL ID: CHEMBL1200386
• Mol file: 73771-04-7.mol

Synonyms:Batmen;Dermatop;HOE 777;HOE-777;Peitel;prednicarbate;prednisolone-17-ethylcarbonate-21-propionate

Chemical Property of Prednicarbate

Chemical Property:

• Appearance/Colour: White cystalline powder
• Vapor Pressure: 4.11E-19mmHg at 25°C
• Melting Point: 110 - 112ºC
• Refractive Index: 1.56
• Boiling Point: 640.7 °C at 760 mmHg
• PKA: 14.05±0.70(Predicted)
• Flash Point: 209.4 °C
• PSA: 116.20000
• Density: 1.25 g/cm³
• LogP: 3.69930
• 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).
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 488.24101810
• Heavy Atom Count: 35
• Complexity: 982

Purity/Quality:

97%-102% ^*data from raw suppliers

Prednicarbate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OCC(=O)C1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)OC(=O)OCC
• Isomeric SMILES: CCC(=O)OCC(=O)[C@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)OC(=O)OCC
• Recent ClinicalTrials: 1404003_OpenPsori.PlaqueTest to Eval.Eff.of Diff.Comp. to Mapracorat
• Recent EU Clinical Trials: A phase IIa, multi-center, randomized, double-blind study to evaluate the anti-mycotic and anti-inflammatory efficacy of topical combinational product LAS 41003 versus corresponding mono-substances in patients with candida infections in intertriginous areas at the trunk
• Description: 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. 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.
• 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.

Technology Process of Prednicarbate

There total 5 articles about Prednicarbate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.1%

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

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 24h;

Reference yield:

prednisolon (50-24-8,8056-11-9) → prednicarbate (73771-04-7)

Guidance literature:

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

With pyridine; water; toluene-4-sulfonic acid; acetic acid; In 1,4-dioxane;

Reference yield:

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

Guidance literature:

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

With pyridine; water; acetic acid;

upstream raw materials:

propionyl chloride

Prednisolone 17-ethylcarbonate

propionic acid anhydride

prednisolon

Downstream raw materials:

prednisolon

Prednisolone 17-ethylcarbonate

11β,17-dihydroxy-21-propionyloxypregna-1,4-diene-3,20-dione

Refernces

• 1、 -. "Method for reducing or preventing transplant rejection in the eye and intraocular implants for use therefor". . . Retrieved 2008/06/13.
• 2、 Stache,Fritsch,Rupp,Hitzel,Fehlhaber. "Synthesis of prednicarbate, an unhalogenated topical antiinflammatory derivative of prednisolone-17-ethylcarbonate-21-propionate". . p. 1753 - 1757. Retrieved 2007/10/02.