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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27FO5
Molecular Weight 378.4345
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FLUPREDNISOLONE

SMILES

C[C@]12C[C@H](O)[C@H]3[C@@H](C[C@H](F)C4=CC(=O)C=C[C@]34C)[C@@H]1CC[C@]2(O)C(=O)CO

InChI

InChIKey=MYYIMZRZXIQBGI-HVIRSNARSA-N
InChI=1S/C21H27FO5/c1-19-5-3-11(24)7-14(19)15(22)8-12-13-4-6-21(27,17(26)10-23)20(13,2)9-16(25)18(12)19/h3,5,7,12-13,15-16,18,23,25,27H,4,6,8-10H2,1-2H3/t12-,13-,15-,16-,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI
Molecular Formula C21H27FO5
Molecular Weight 378.4345
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/5818823 | http://www.tabletwise.com/us/alphadrol-tablet

Fluprednisolone is glucocorticoid with the general properties of the corticosteroids. It is the drug of choice for all conditions in which routine systemic corticosteroid therapy is indicated (hypersensitivity dermatoses, contact dermatitis, pemphigus, pemphigoid, lupus erythematosus, neoplasia etc), except adrenal deficiency states.

Originator

Approval Year

1960
105
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
ALPHADROL

Approved Use

Unknown

Launch Date

1978
Primary
Approved
8583
ALPHADROL

Approved Use

Unknown

Launch Date

1978
Primary
Approved
8583
ALPHADROL

Approved Use

Unknown

Launch Date

1978
Doses

Doses

DosePopulationAdverse events​
5.25 mg/m2 1 times / day multiple, oral
Highest studied dose
Dose: 5.25 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 5.25 mg/m2, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/13884715
unhealthy, 0-16
Health Status: unhealthy
Age Group: 0-16
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/13884715
Sources:
https://pubmed.ncbi.nlm.nih.gov/13884715
5.25 mg 1 times / day multiple, oral
Dose: 5.25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 5.25 mg, 1 times / day
Sources:
https://www.sciencedirect.com/science/article/abs/pii/002187076290093X
unhealthy, children
Health Status: unhealthy
Age Group: children
Sex: M+F
Sources:
https://www.sciencedirect.com/science/article/abs/pii/002187076290093X
Sources:
https://www.sciencedirect.com/science/article/abs/pii/002187076290093X
Sourcing

Sourcing

Vendor/AggregatorIDURL
AK Scientific, Inc. (AKSCI)
67609
http://www.aksci.com/item_detail.php?cat=67609
Alfa Chemistry
53-34-9
https://www.alfa-chemistry.com/cas_53-34-9.htm
Ambinter
Amb22167256
http://www.ambinter.com/reference/22167256
Aurora Fine Chemicals LLC
A17.901.881
http://online.aurorafinechemicals.com/info?ID=A17.901.881
ChemMol
49401269
http://www.chemmol.com/chemmol/49401269.html
DC Chemicals
DC37474
http://www.dcchemicals.com//product_show-Fluprednisolone.html
Hairui
HR135192
http://www.hairuichem.com/en/product/53-34-9.html
iChemical
EBD2293287
http://www.ichemical.com/products/53-34-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
LGC Standards
DRE-A13797900AL-100
https://www.lgcstandards.com/US/en/p/DRE-A13797900AL-100
LGC Standards
DRE-C13797900
https://www.lgcstandards.com/US/en/p/DRE-C13797900
MolPort
MolPort-006-110-097
https://www.molport.com/shop/molecule-link/MolPort-006-110-097
MuseChem
R025034
https://www.musechem.com/product/R025034.html
OChem
11920
http://www.ocheminc.com/index.php?act=psearch&pid=053F349
Sigma-Aldrich
34206_SIAL
https://www.sigmaaldrich.com/catalog/product/sial/34206?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule
S528201
http://www.smolecule.com/products/s528201
Smolecule
S748721
https://www.smolecule.com/products/s748721
THE BioTek
bt-268365
https://www.thebiotek.com/product/inhibitors/bt-268365
PubMed

PubMed

TitleDatePubMed
Intraocular pressure elevation from topical difluprednate use.
2010-12
Pathology in practice. Pemphigus foliaceous.
2010-11-01
Durezol (Difluprednate Ophthalmic Emulsion 0.05%) compared with Pred Forte 1% ophthalmic suspension in the treatment of endogenous anterior uveitis.
2010-10
Metabolic profiles of difluprednate in rabbit ocular tissues after instillation of difluprednate ophthalmic emulsion.
2010-08
Steroid eye drop treatment (difluprednate ophthalmic emulsion) is effective in reducing refractory diabetic macular edema.
2010-06
New drugs 09, part 2.
2009-06
Difluprednate ophthalmic emulsion 0.05% for postoperative inflammation and pain.
2009-01
New drugs: Clevidipine butyrate, difluprednate, and tetrabenazine.
2008-11-21
Effect of isoflupredone acetate with or without insulin on energy metabolism, reproduction, milk production, and health in dairy cows in early lactation.
2007-09
Effects of dexamethasone and isoflupredone acetate on plasma potassium concentrations and other biochemical measurements in dairy cows in early lactation.
2006-07
Topical steroid and antibiotic combination therapy in red eye conditions.
2006-04
Injection site with generalized rash caused by pegylated interferon alpha 2a injection.
2006
Formulation of an ophthalmic lipid emulsion containing an anti-inflammatory steroidal drug, difluprednate.
2005-09-14
Conjunctival lymphoid hyperplasia presenting with bilateral panuveitis.
2005-03
Cutaneous reactions to imatinib mesylate treated by topical steroid.
2005-03
[Traumatic lesion of the optic nerve head by flying fish: a case report].
2004-05
Evaluation of exogenous glucocorticoid injection on preweaning growth performance of neonatal pigs under commercial conditions.
2004-04
Effects of two anti-inflammatory drugs on physiologic variables and milk production in cows with endotoxin-induced mastitis.
2004-01
Comparison of efficacy and tolerability of isoflupredone and dexamethasone in the treatment of horses affected with recurrent airway obstruction ('heaves').
2003-06
Pharmacodynamics of isoflupredone acetate in an endotoxin-induced mastitis model.
2003-03
Analysis of an anti-inflammatory steroidal drug, difluprednate, in aqueous humor by combination of semi-micro HPLC and column switching method.
2003-01-15
Effect of chirality at C-20 of methyl 11beta,17alpha,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate derivatives on antiinflammatory activity.
2002-04
[Severe hypokalemic episode induced by abuse of fluoro-prednisolone acetate administered nasally and the simultaneous oral consumption of indapamide].
1985-01-31
Patents

Patents

WO 2016170102
1

Sample Use Guides

In Vivo Use Guide
A dose of 3 mg per kilogram in dogs for a period of two weeks produced no toxic effects.
Route of Administration: Oral
In Vitro Use Guide
Lymphosarcoma P1798 cells was treated with 9FP (Fluprednisolone). Ribonuclease activity of the cells was measured after incubation with 0.1 mkg/ml 9FP (Fluprednisolone) for various time periods (from 6 to 48 h). Cells also develop increased acid ribonuclease activity after incubation with 9FP (Fluprednisolone) in vitro.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:49:05 GMT 2025
Edited
by admin
on Mon Mar 31 17:49:05 GMT 2025
Record UNII
9H05937G3X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ALPHADROL
Preferred Name English
FLUPREDNISOLONE
HSDB   INN   MART.   MI   ORANGE BOOK   USAN   WHO-DD  
INN   USAN  
Official Name English
6?-Fluoro-11?,17,21-trihydroxypregna-1,4-diene-3,20-dione
Systematic Name English
NSC-47439
Code English
FLUPREDNISOLONE [HSDB]
Common Name English
U-7800
Code English
fluprednisolone [INN]
Common Name English
PREGNA-1,4-DIENE-3,20-DIONE, 6-FLUORO-11,17,21-TRIHYDROXY-, (6.ALPHA.,11.BETA.)-
Systematic Name English
FLUPREDNISOLONE [ORANGE BOOK]
Common Name English
FLUPREDNISOLONE [MART.]
Common Name English
FLUPREDNISOLONE [MI]
Common Name English
Fluprednisolone [WHO-DD]
Common Name English
FLUPREDNISOLONE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C521
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
Code System Code Type Description
MESH
D005477
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
HSDB
3335
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
WIKIPEDIA
FLUPREDNISOLONE
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID5046067
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
EVMPD
SUB07736MIG
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
CAS
53-34-9
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
NCI_THESAURUS
C65730
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
MERCK INDEX
m5493
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY Merck Index
DRUG CENTRAL
1216
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
PUBCHEM
5876
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
INN
1352
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
FDA UNII
9H05937G3X
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
SMS_ID
100000080742
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
NSC
47439
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
DRUG BANK
DB09378
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-170-8
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL1200774
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY
RXCUI
4497
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
PRIMARY RxNorm
Related Record Type Details
Structure of FLUPREDNISOLONE
ACTIVE MOIETY
NIH
NCATS
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