FLUPREDNISOLONE

US Previously Marketed

First approved in 1960

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 Search

SMILES

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

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13892052
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

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172 Target ID: CHEMBL2034 Sources: https://www.ncbi.nlm.nih.gov/pubmed/92477	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Contact dermatitis 20 Sources: http://www.tabletwise.com/us/alphadrol-tablet	Primary	Approved 8429	ALPHADROL Approved Use Unknown Launch Date 2.77948793E11
Pemphigus 1 Sources: http://www.tabletwise.com/us/alphadrol-tablet	Primary	Approved 8429	ALPHADROL Approved Use Unknown Launch Date 2.77948793E11
Lupus erythematosus 2 Sources: http://www.tabletwise.com/us/alphadrol-tablet	Primary	Approved 8429	ALPHADROL Approved Use Unknown Launch Date 2.77948793E11

Doses

Dose	Population	Adverse events
5.25 mg/m2 1 times / day multiple, oral (max) 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 n = 45 Health Status: unhealthy Condition: Bronchial asthma Age Group: 0-16 Sex: M+F Population Size: 45 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 n = 45 Health Status: unhealthy Condition: asthma Age Group: children Sex: M+F Population Size: 45 Sources: https://www.sciencedirect.com/science/article/abs/pii/002187076290093X	Sources: https://www.sciencedirect.com/science/article/abs/pii/002187076290093X

Sourcing

Vendor/Aggregator	ID	URL
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
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
iChemical	EBD2293287	http://www.ichemical.com/products/53-34-9.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
[Severe hypokalemic episode induced by abuse of fluoro-prednisolone acetate administered nasally and the simultaneous oral consumption of indapamide].	1985 Jan 31	4017458
Effect of chirality at C-20 of methyl 11beta,17alpha,20-trihydroxy-3-oxo-1,4-pregnadien-21-oate derivatives on antiinflammatory activity.	2002 Apr	11958791
Analysis of an anti-inflammatory steroidal drug, difluprednate, in aqueous humor by combination of semi-micro HPLC and column switching method.	2003 Jan 15	12485714
Comparison of efficacy and tolerability of isoflupredone and dexamethasone in the treatment of horses affected with recurrent airway obstruction ('heaves').	2003 Jun	12880012
Pharmacodynamics of isoflupredone acetate in an endotoxin-induced mastitis model.	2003 Mar	12703615
Evaluation of exogenous glucocorticoid injection on preweaning growth performance of neonatal pigs under commercial conditions.	2004 Apr	15080348
Effects of two anti-inflammatory drugs on physiologic variables and milk production in cows with endotoxin-induced mastitis.	2004 Jan	14719704
[Traumatic lesion of the optic nerve head by flying fish: a case report].	2004 May	15162294
Conjunctival lymphoid hyperplasia presenting with bilateral panuveitis.	2005 Mar	15767083
Cutaneous reactions to imatinib mesylate treated by topical steroid.	2005 Mar	15726597
Formulation of an ophthalmic lipid emulsion containing an anti-inflammatory steroidal drug, difluprednate.	2005 Sep 14	16023810
Injection site with generalized rash caused by pegylated interferon alpha 2a injection.	2006	16319482
Topical steroid and antibiotic combination therapy in red eye conditions.	2006 Apr	16611527
Effects of dexamethasone and isoflupredone acetate on plasma potassium concentrations and other biochemical measurements in dairy cows in early lactation.	2006 Jul	16817750
Effect of isoflupredone acetate with or without insulin on energy metabolism, reproduction, milk production, and health in dairy cows in early lactation.	2007 Sep	17699036
New drugs: Clevidipine butyrate, difluprednate, and tetrabenazine.	2008 Nov-Dec	19019814
Difluprednate ophthalmic emulsion 0.05% for postoperative inflammation and pain.	2009 Jan	19101421
New drugs 09, part 2.	2009 Jun	19474606
Metabolic profiles of difluprednate in rabbit ocular tissues after instillation of difluprednate ophthalmic emulsion.	2010 Aug	20509750
Intraocular pressure elevation from topical difluprednate use.	2010 Dec	21111374
Steroid eye drop treatment (difluprednate ophthalmic emulsion) is effective in reducing refractory diabetic macular edema.	2010 Jun	20180131
Pathology in practice. Pemphigus foliaceous.	2010 Nov 1	21034341
Durezol (Difluprednate Ophthalmic Emulsion 0.05%) compared with Pred Forte 1% ophthalmic suspension in the treatment of endogenous anterior uveitis.	2010 Oct	20809807

Patents

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 `Fri Dec 15 15:10:38 UTC 2023` Edited by `admin` on `Fri Dec 15 15:10:38 UTC 2023`
Record UNII	9H05937G3X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FLUPREDNISOLONE

Official Name

English

6α-Fluoro-11β,17,21-trihydroxypregna-1,4-diene-3,20-dione

Systematic Name

English

NSC-47439

Code

English

ALPHADROL

Brand Name

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