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
