Difluprednate

Difluprednate
Clinical data
AHFS/Drugs.com	Monograph
MedlinePlus	a609025
License data	US FDA: Difluprednate;
Routes of; administration	eye drops
ATC code	D07AC19 (WHO) ;
Legal status
Legal status	US: ℞-only ;
Identifiers
	IUPAC 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;
CAS Number	23674-86-4 ;
PubChem CID	32037;
DrugBank	DB06781 ;
ChemSpider	391990 ;
UNII	S8A06QG2QE;
KEGG	D01266 ;
ChEBI	CHEBI:31485;
ChEMBL	ChEMBL1201749 ;
CompTox Dashboard (EPA)	DTXSID0046773 ;
ECHA InfoCard	100.041.636
Chemical and physical data
Formula	C27H34F2O7
Molar mass	508.559 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]12CC[C@](OC(=O)CCC)(C(=O)COC(C)=O)[C@@]1(C)C[C@H](O)[C@@]1(F)[C@@]2([H])C[C@H](F)C2=CC(=O)C=C[C@]12C;
	InChI InChI=1S/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; Key:WYQPLTPSGFELIB-JTQPXKBDSA-N;
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Difluprednate is a corticosteroid, It is chemically a butyrate ester of 6(alpha),9(alpha)-difluoro prednisolone acetate. Accordingly, difluprednate is sometimes abbreviated DFBA, for difluoroprednisolone butyrate acetate.

Approval

On June 24, 2008, the US Food and Drug Administration (FDA) approved difluprednate for the treatment of post-operative ocular inflammation and pain.[1] It is marketed by Alcon under the tradename Durezol.

Clinical trials

Difluprednate ophthalmic emulsion 0.05% is also being studied in other ocular inflammatory diseases, including a phase 3 study evaluating difluprednate for the treatment of anterior uveitis[2][3]

References

"Sirion Therapeutics Announces FDA Approval of Durezol for Treatment of Postoperative Ocular Inflammation and Pain" (Press release). Sirion Therapeutics, Inc. 2008-06-24. Retrieved 2008-06-30.
Clinical trial number NCT00501579 for "Study of Difluprednate in the Treatment of Uveitis" at ClinicalTrials.gov
Sheppard JD, Toyos MM, Kempen JH, Kaur P, Foster CS (May 2014). "Difluprednate 0.05% versus prednisolone acetate 1% for endogenous anterior uveitis: a phase III, multicenter, randomized study". Investigative Ophthalmology & Visual Science. 55 (5): 2993–3002. doi:10.1167/iovs.13-12660. PMC 4581692. PMID 24677110.

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[1] "Sirion Therapeutics Announces FDA Approval of Durezol for Treatment of Postoperative Ocular Inflammation and Pain" (Press release). Sirion Therapeutics, Inc. 2008-06-24. Retrieved 2008-06-30.

[2] Clinical trial number NCT00501579 for "Study of Difluprednate in the Treatment of Uveitis" at ClinicalTrials.gov

[Sheppard_2014-3] Sheppard JD, Toyos MM, Kempen JH, Kaur P, Foster CS (May 2014). "Difluprednate 0.05% versus prednisolone acetate 1% for endogenous anterior uveitis: a phase III, multicenter, randomized study". Investigative Ophthalmology & Visual Science. 55 (5): 2993–3002. doi:10.1167/iovs.13-12660. PMC 4581692. PMID 24677110.