U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H34F2O7
Molecular Weight 508.5525
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIFLUPREDNATE

SMILES

CCCC(=O)O[C@@]1(CC[C@@]2([H])[C@]3([H])C[C@@]([H])(C4=CC(=O)C=C[C@]4(C)[C@]3([C@]([H])(C[C@@]21C)O)F)F)C(=O)COC(=O)C

InChI

InChIKey=WYQPLTPSGFELIB-JTQPXKBDSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/2008/022212s000_Lbl.pdf

Difluprednate is a corticosteroid used as an anti-inflammatory steroidal drug used primarily in ocular surgery. It is thought to act by the induction of phospholipase A2 inhibitory proteins (lipocortins). It is postulated that these proteins control the biosynthesis of potent mediators of infammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. It is marketed by Alcon under the tradename Durezol.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.57 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Durezol

Approved Use

Durezol® (difluprednate ophthalmic emulsion) 0.05%, a topical corticosteroid, is indicated for the treatment of inflammation and pain associated with ocular surgery. ​Durezol is also indicated for the treatment of endogenous anterior uveitis.

Launch Date

1.2140928E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3 ng/mL
2.5 μL single, ocular
dose: 2.5 μL
route of administration: Ocular
experiment type: SINGLE
co-administered:
DIFLUPREDNATE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
8.61 ng × h/mL
2.5 μL single, ocular
dose: 2.5 μL
route of administration: Ocular
experiment type: SINGLE
co-administered:
DIFLUPREDNATE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
8 h
2.5 μL single, ocular
dose: 2.5 μL
route of administration: Ocular
experiment type: SINGLE
co-administered:
DIFLUPREDNATE plasma
Oryctolagus cuniculus
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
1 drop 9 times / day multiple, topical
Highest studied dose
Dose: 1 drop, 9 times / day
Route: topical
Route: multiple
Dose: 1 drop, 9 times / day
Sources: Page: p.2
unhealthy, 56.7 ± 17.9
n = 33
Health Status: unhealthy
Condition: Corneal graft rejection
Age Group: 56.7 ± 17.9
Sex: M+F
Population Size: 33
Sources: Page: p.2
Disc. AE: Intraocular pressure increased, Toxic epitheliolysis...
AEs leading to
discontinuation/dose reduction:
Intraocular pressure increased (18.2%)
Toxic epitheliolysis (grade 1-2, 21.2%)
Sources: Page: p.2
1 drop 4 times / day multiple, topical
Recommended
Dose: 1 drop, 4 times / day
Route: topical
Route: multiple
Dose: 1 drop, 4 times / day
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Inflammation and pain associated with ocular surgery
Sources: Page: p.2
Other AEs: IOP increased, Cataract...
Other AEs:
IOP increased
Cataract
Healing delayed
Bacterial infection
Infection viral
Fungal infection
Sources: Page: p.2
AEs

AEs

AESignificanceDosePopulation
Intraocular pressure increased 18.2%
Disc. AE
1 drop 9 times / day multiple, topical
Highest studied dose
Dose: 1 drop, 9 times / day
Route: topical
Route: multiple
Dose: 1 drop, 9 times / day
Sources: Page: p.2
unhealthy, 56.7 ± 17.9
n = 33
Health Status: unhealthy
Condition: Corneal graft rejection
Age Group: 56.7 ± 17.9
Sex: M+F
Population Size: 33
Sources: Page: p.2
Toxic epitheliolysis grade 1-2, 21.2%
Disc. AE
1 drop 9 times / day multiple, topical
Highest studied dose
Dose: 1 drop, 9 times / day
Route: topical
Route: multiple
Dose: 1 drop, 9 times / day
Sources: Page: p.2
unhealthy, 56.7 ± 17.9
n = 33
Health Status: unhealthy
Condition: Corneal graft rejection
Age Group: 56.7 ± 17.9
Sex: M+F
Population Size: 33
Sources: Page: p.2
Bacterial infection
1 drop 4 times / day multiple, topical
Recommended
Dose: 1 drop, 4 times / day
Route: topical
Route: multiple
Dose: 1 drop, 4 times / day
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Inflammation and pain associated with ocular surgery
Sources: Page: p.2
Cataract
1 drop 4 times / day multiple, topical
Recommended
Dose: 1 drop, 4 times / day
Route: topical
Route: multiple
Dose: 1 drop, 4 times / day
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Inflammation and pain associated with ocular surgery
Sources: Page: p.2
Fungal infection
1 drop 4 times / day multiple, topical
Recommended
Dose: 1 drop, 4 times / day
Route: topical
Route: multiple
Dose: 1 drop, 4 times / day
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Inflammation and pain associated with ocular surgery
Sources: Page: p.2
Healing delayed
1 drop 4 times / day multiple, topical
Recommended
Dose: 1 drop, 4 times / day
Route: topical
Route: multiple
Dose: 1 drop, 4 times / day
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Inflammation and pain associated with ocular surgery
Sources: Page: p.2
IOP increased
1 drop 4 times / day multiple, topical
Recommended
Dose: 1 drop, 4 times / day
Route: topical
Route: multiple
Dose: 1 drop, 4 times / day
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Inflammation and pain associated with ocular surgery
Sources: Page: p.2
Infection viral
1 drop 4 times / day multiple, topical
Recommended
Dose: 1 drop, 4 times / day
Route: topical
Route: multiple
Dose: 1 drop, 4 times / day
Sources: Page: p.2
unhealthy
Health Status: unhealthy
Condition: Inflammation and pain associated with ocular surgery
Sources: Page: p.2
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Neuronal cell bodies in the hypothalamic paraventricular nucleus mediate stress-induced renin and corticosterone secretion.
1989 Jul
The role of difluprednate ophthalmic emulsion in clinical practice.
2009
Pharmacokinetic features of difluprednate ophthalmic emulsion in rabbits as determined by glucocorticoid receptor-binding bioassay.
2011 Feb
Patents

Sample Use Guides

Ocular Surgery Instill one drop into the conjunctival sac of the affected eye 4 times daily beginning 24 hours after surgery and continuing throughout the first 2 weeks of the postoperative period, followed by 2 times daily for a week and then a taper based on the response. Endogenous Anterior Uveitis Instill one drop into the conjunctival sac of the affected eye 4 times daily for 14 days followed by tapering as clinically indicated.
Route of Administration: Topical
Difluprednate exhibited GR agonistic activity in GR-CALUX assay with EC50 value 0.57nM
Name Type Language
DIFLUPREDNATE
DASH   INN   JAN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
DIFLUPREDNATE [INN]
Common Name English
DIFLUPREDNATE [USAN]
Common Name English
6.ALPHA.,9-DIFLUORO-11.BETA.,17,21-TRIHYDROXYPREGNA-1,4-DIENE-3,20-DIONE 21-ACETATE 17-BUTYRATE
Common Name English
DIFLUPREDNATE [VANDF]
Common Name English
DIFLUPREDNATE [MI]
Common Name English
DUREZOL
Brand Name English
DIFLUPREDNATE [WHO-DD]
Common Name English
W 6309
Code English
DIFLUPREDNATE [JAN]
Common Name English
W-6309
Code English
DIFLUPREDNATE [MART.]
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-6,9-DIFLUORO-11-HYDROXY-17-(1-OXOBUTOXY)-, (6.ALPHA.,11.BETA.)-
Systematic Name English
DIFLUPREDNATE [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
WHO-VATC QD07AC19
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
FDA ORPHAN DRUG 265608
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
WHO-ATC D07AC19
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
Code System Code Type Description
MESH
C015808
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
EVMPD
SUB07131MIG
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
NCI_THESAURUS
C80259
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
DRUG CENTRAL
3142
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
IUPHAR
7474
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
DRUG BANK
DB06781
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
RXCUI
23043
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
DIFLUPREDNATE
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-815-4
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
FDA UNII
S8A06QG2QE
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
MERCK INDEX
M4441
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY Merck Index
INN
2652
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
EPA CompTox
23674-86-4
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
CAS
23674-86-4
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
PUBCHEM
443936
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
LACTMED
Difluprednate
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201749
Created by admin on Sat Jun 26 00:26:28 UTC 2021 , Edited by admin on Sat Jun 26 00:26:28 UTC 2021
PRIMARY