FLUNISOLIDE ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H31FO6
Molecular Weight	434.4977
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@@]12C[C@@]3([H])[C@]4([H])C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@@]4([H])[C@@H](O)C[C@]3(C)[C@@]1(OC(C)(C)O2)C(=O)CO

InChI

InChIKey=XSFJVAJPIHIPKU-XWCQMRHXSA-N

InChI=1S/C24H31FO6/c1-21(2)30-19-9-14-13-8-16(25)15-7-12(27)5-6-22(15,3)20(13)17(28)10-23(14,4)24(19,31-21)18(29)11-26/h5-7,13-14,16-17,19-20,26,28H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,20+,22-,23-,24+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C24H31FO6
Molecular Weight	434.4977
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Flunisolide is a synthetic corticosteroid. It is administered either as an oral metered-dose inhaler for the treatment of asthma or as a nasal spray for treating allergic rhinitis. Corticosteroids are naturally occurring hormones that prevent or suppress inflammation and immune responses. When given as an intranasal spray, flunisolide reduces watery nasal discharge (rhinorrhea), nasal congestion, postnasal drip, sneezing, and itching oat the back of the throat that are common allergic symptoms. Flunisolide is a glucocorticoid receptor agonist. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. Flunisolide binds to plasma transcortin, and it becomes active when it is not bound to transcortin. It is used for the maintenance treatment of asthma as a prophylactic therapy. Flunisolide is marketed as AeroBid, Nasalide, Nasarel.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glucocorticoid receptor 172	Agonist 2,678
eosinophils 3	Inhibitor 8,297		32.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Perennial or seasonal allergic rhinitis 6	Primary		Approved 8,429	FLUNISOLIDE

C_max

Value	Dose	Co-administered	Analyte	Population
1 ng/mL	160 μg 2 times / day multiple, respiratory		FLUNISOLIDE unknown	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1.2 ng × h/mL	160 μg 2 times / day multiple, respiratory		FLUNISOLIDE unknown	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.7 h	0.5 mg single, respiratory		FLUNISOLIDE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
20%	0.5 mg single, respiratory		FLUNISOLIDE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
160 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 217	Other AEs: Headache, Fever...
320 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 113	Other AEs: Headache, Fever...
80 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 189	Other AEs: Headache, Fever...
85 ug 2 times / day steady, respiratory	unhealthy, 6-11 years n = 510	Disc. AE: Asthma, Pharyngitis...

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AEs

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AE	Significance	Dose	Population
Epistaxis	0.9%	160 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 217
Infection	0.9%	160 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 217
Urinary tract infection	0.9%	160 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 217
Headache	13.8%	160 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 217
Rhinitis	15.7%	160 ug 2 times / day steady, respiratory (starting) Recommended	unhealthy, 4-78 years n = 217

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1,537

Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1,737	substrate 3,367	yes
P-gp 1,537	substrate 3,367	yes

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PubMed

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Title	Date	PubMed
[Therapeutic effect of the association between pulmonary ventilation and aerosol--inhalation with sulphureous mineral water in the chronic bronchopneumopathies].	2004 Apr	15354759
In vitro effects of flunisolide on MMP-9, TIMP-1, fibronectin, TGF-beta1 release and apoptosis in sputum cells freshly isolated from mild to moderate asthmatics.	2004 Sep	15291899
How do topical nasal corticosteroids improve sleep and daytime somnolence in allergic rhinitis?	2005 Dec	16337455
Efficacy of nebulized flunisolide combined with salbutamol and ipratropium bromide in stable patients with moderate-to-severe chronic obstructive pulmonary disease.	2006	16293958
New treatment options in allergic rhinitis: patient considerations and the role of ciclesonide.	2008 Apr	18728855

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Patents

Sample Use Guides

In Vivo Use Guide

Initial dose: 2 sprays in each nostril 2 times a day. If needed, this dose may be increased to 2 sprays in each nostril 3 times a day. Maximum total daily doses should not exceed 8 sprays in each nostril.

Route of Administration: Nasal

In Vitro Use Guide

Flunisolide at all the tested concentrations ((0.1 to 10 uM) effectively inhibited ICAM-1 expression and GM-CSF and IL-5 release. The percent inhibition induced by the highest flunisolide concentration (10 uM) for the various BEAS-2B functions was 30%, 60%, and 70%, respectively.

Substance Class	Chemical
Record UNII	78M02AA8KF
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

FLUNISOLIDE ANHYDROUS

Common Name

English

FLUNISOLIDE [MI]

Common Name

English

6.ALPHA.-FLUORO-11.BETA.,16.ALPHA.,17,21-TETRAHYDROXYPREGNA-1,4-DIENE-3,20-DIONE CYCLIC 16,17-ACETAL WITH ACETONE

Common Name

English

flunisolide [INN]

Common Name

English

PREGNA-1,4-DIENE-3,20-DIONE, 6-FLUORO-11,21-DIHYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))- (6.ALPHA.,11.BETA.,16.ALPHA.)-

Common Name

English

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Classification Tree

Code System

Code

Glucocorticoids

WHO-ATC

R03BA03

Corticosteroids

WHO-ATC

R01AD04

Established Pharmacologic Class

NDF-RT

N0000175576

Steroid Hormone Receptor Agonists

NDF-RT

N0000175450

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Code System

Code

Type

Description

RXCUI

1546428

PRIMARY

FDA UNII

78M02AA8KF

PRIMARY

DAILYMED

78M02AA8KF

PRIMARY

CHEBI

5106

PRIMARY

NCI_THESAURUS

C132268

PRIMARY

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Type

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					78M02AA8KF

FLUNISOLIDE ANHYDROUS

ACTIVE MOIETY

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SMILES

InChI

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as victim

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound