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23674-86-4

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23674-86-4 Usage

Description

Difluprednate is a synthetic glucocorticoid, specifically a derivative of prednisolone, with potent glucocorticoid receptor activation (Ki = 78 pM). It is a white solid and is being developed as a topical ophthalmic emulsion for the treatment of inflammatory eye diseases.

Uses

Used in Pharmaceutical Industry:
Difluprednate is used as an anti-inflammatory agent for the treatment of post-operative ocular inflammation. It is also used to treat diabetic macular edema and inflammation following cataract surgery.
Used in Ophthalmology:
Difluprednate is used as a corticosteroid in the form of Difluprednate-d3, which is the isotope labeled form of Difluprednate (D445925). It is approved for the treatment of post-operative ocular inflammation and is being developed as a topical ophthalmic emulsion to treat inflammatory eye diseases.
Used in Research:
Difluprednate-d3, as an isotope labeled form, is utilized in research for studying the pharmacokinetics, metabolism, and distribution of Difluprednate in various biological systems.

Originator

Epitopic,Clin Midy,France,1978

Manufacturing Process

Orthoesterification: A mixture of 1 g of 6α,9α-difluoroprednisolone, 10 mg of p-toluenesulfonic acid, 5 cc of dimethylformamide and 3 cc of methyl orthobutyrate is heated for 15 hours on an oil bath at 105°C while a slow stream of nitrogen is passed through the mixture so that the methanol produced as a by-product of the reaction, is distilled off. After addition of several drops of pyridine to neutralize the acid catalyst, the reaction mixture is evaporated under vacuum and there is obtained a solid residue which is taken up with methanol, and filtered. The product is recrystallized from a methylene chloride-methanol mixture to yield 682 mg of 6α,9αdifluoroprednisolone 17α,21-methylorthobutyrate, also identified as 17α,21- (1'-methoxy)-n-butylidenedioxy-6α,9α-difluoro-δ1,4-pregnadiene-11β-ol-3,20- dione, MP 194°C-198°C.Upon chromatography of the mother liquor on a column of alumina another 338 mg of a crystalline mixture of the epimeric orthobutyrates are isolated.Hydrolysis: A suspension of 1 g of the 6α,9α-difluoroprednisolone 17α,21- methylorthobutyrate in 10 cc of methanol is treated with 2 cc of a 2 N aqueous solution of oxalic acid and heated on a water bath at 40°-50°C for about 5-10 minutes and, afterwards, the mixture is concentrated under vacuum. The residue is then shaken with water, the insoluble product is filtered off and then dried. The solid material is recrystallized from acetoneether and 6α,9α-difluoroprednisolone 17-butyrate is obtained, MP 193°-196°CEsterification: A solution of 500 mg of 6α,9α-difluoroprednisolone-17-butyrate in 2.5 cc of pyridine is treated with 1.25 cc of acetic anhydride and the reaction mixture permitted to stand overnight at 0°C. The reaction mixture is then poured into ice water and the crystalline precipitate formed is filtered off and recrystallized from a methylene chloride-ether-petroleum ether mixture to yield 494 mg of 6α,9α-difluoroprednisolone 17-butyrate, 21-acetate; MP 191°- 194°C.

Therapeutic Function

Antiinflammatory

Check Digit Verification of cas no

The CAS Registry Mumber 23674-86-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,6,7 and 4 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 23674-86:
(7*2)+(6*3)+(5*6)+(4*7)+(3*4)+(2*8)+(1*6)=124
124 % 10 = 4
So 23674-86-4 is a valid CAS Registry Number.
InChI:InChI=1/C27H34F2O7/c1-5-6-23(34)36-26(22(33)14-35-15(2)30)10-8-17-18-12-20(28)19-11-16(31)7-9-24(19,3)27(18,29)21(32)13-25(17,26)4/h7,9,11,17-18,20-21,32H,5-6,8,10,12-14H2,1-4H3/t17-,18-,20-,21-,24-,25-,26-,27-/m0/s1

23674-86-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name [(6S,8S,9R,10S,11S,13S,14S,17R)-17-(2-acetyloxyacetyl)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] butanoate

1.2 Other means of identification

Product number -
Other names Durezol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:23674-86-4 SDS

23674-86-4Upstream product

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