FLUNISOLIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C24H31FO6.H2O
Molecular Weight	887.0108
Optical Activity	UNSPECIFIED
Defined Stereocenters	18 / 18
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CC1(C)O[C@@H]2C[C@H]3[C@@H]4C[C@H](F)C5=CC(=O)C=C[C@]5(C)[C@H]4[C@@H](O)C[C@]3(C)[C@@]2(O1)C(=O)CO.CC6(C)O[C@@H]7C[C@H]8[C@@H]9C[C@H](F)C%10=CC(=O)C=C[C@]%10(C)[C@H]9[C@@H](O)C[C@]8(C)[C@@]7(O6)C(=O)CO

InChI

InChIKey=MIXMJCQRHVAJIO-TZHJZOAOSA-N

InChI=1S/2C24H31FO6.H2O/c2*1-21(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;/h2*5-7,13-14,16-17,19-20,26,28H,8-11H2,1-4H3;1H2/t2*13-,14-,16-,17-,19+,20+,22-,23-,24+;/m00./s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C24H31FO6
Molecular Weight	434.4977
Charge	0
Count

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

Description
Sources: http://www.drugbank.ca/drugs/DB00180
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/pro/flunisolide.html

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 173 Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00180	Agonist 2752
eosinophils 3 Target ID: CHEMBL614636 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9756205	Inhibitor 8504		32.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Perennial or seasonal allergic rhinitis 6 Sources: https://www.drugs.com/pro/flunisolide.html	Primary		Approved 8583	FLUNISOLIDE Approved Use Flunisolide Nasal Solution is indicated for the treatment of the nasal symptoms of seasonal or perennial rhinitis. Launch Date 2002

C_max

Value	Dose	Co-administered	Analyte	Population
3.4 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021247s008lbl.pdf	160 μg 2 times / day steady-state, respiratory dose: 160 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered:		FLUNISOLIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
9.4 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9505980	3 mg single, respiratory dose: 3 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUNISOLIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
4.7 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021247s008lbl.pdf	160 μg 2 times / day steady-state, respiratory dose: 160 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered:		FLUNISOLIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
14.2 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9505980	3 mg single, respiratory dose: 3 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUNISOLIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/021247s008lbl.pdf	160 μg 2 times / day steady-state, respiratory dose: 160 μg route of administration: Respiratory experiment type: STEADY-STATE co-administered:		FLUNISOLIDE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN
1.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9505980	3 mg single, respiratory dose: 3 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUNISOLIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
20% EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/9505980	3 mg single, respiratory dose: 3 mg route of administration: Respiratory experiment type: SINGLE co-administered:		FLUNISOLIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
160 ug 2 times / day steady, respiratory Recommended Dose: 160 ug, 2 times / day Route: respiratory Route: steady Dose: 160 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf	unhealthy, 4-78 years Health Status: unhealthy Age Group: 4-78 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf	Other AEs: Headache, Fever... Other AEs: Headache (13.8%) Fever (3.7%) Allergic reaction (4.6%) Pain (4.6%) Accidental injury (3.7%) Infection (0.9%) Back pain (3.2%) Vomiting (4.6%) Dyspepsia (3.2%) Pharyngitis (16.6%) Rhinitis (15.7%) Cough increased (5.5%) Sinusitis (4.1%) Epistaxis (0.9%) Rash (3.7%) Urinary tract infection (0.9%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf
320 ug 2 times / day steady, respiratory Recommended Dose: 320 ug, 2 times / day Route: respiratory Route: steady Dose: 320 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf	unhealthy, 4-78 years Health Status: unhealthy Age Group: 4-78 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf	Other AEs: Headache, Fever... Other AEs: Headache (8.8%) Fever (0.9%) Allergic reaction (4.4%) Pain (1.8%) Accidental injury (3.5%) Infection (0.9%) Back pain (1.8%) Dyspepsia (3.5%) Pharyngitis (16.8%) Rhinitis (3.5%) Cough increased (1.8%) Sinusitis (8.8%) Rash (1.8%) Urinary tract infection (3.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf
80 ug 2 times / day steady, respiratory Recommended Dose: 80 ug, 2 times / day Route: respiratory Route: steady Dose: 80 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf	unhealthy, 4-78 years Health Status: unhealthy Age Group: 4-78 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf	Other AEs: Headache, Fever... Other AEs: Headache (9%) Fever (6.9%) Allergic reaction (4.2%) Pain (2.6%) Accidental injury (3.7%) Infection (3.7%) Back pain (0.5%) Vomiting (4.2%) Dyspepsia (2.1%) Pharyngitis (17.5%) Rhinitis (9%) Cough increased (8.5%) Sinusitis (7.4%) Epistaxis (3.2%) Rash (2.6%) Urinary tract infection (1.1%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/021247LBL.pdf
85 ug 2 times / day steady, respiratory Dose: 85 ug, 2 times / day Route: respiratory Route: steady Dose: 85 ug, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021247s000_ClinPharmR.pdf	unhealthy, 6-11 years Health Status: unhealthy Age Group: 6-11 years Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021247s000_ClinPharmR.pdf	Disc. AE: Asthma, Pharyngitis... AEs leading to discontinuation/dose reduction: Asthma (10%) Pharyngitis (1.7%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021247s000_ClinPharmR.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2006/021247s000_ClinPharmR.pdf Page: 16.0	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11724763/	yes

PubMed

Title	Date	PubMed
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.	2008-11-04	18983670
Molecular and clinical pharmacology of intranasal corticosteroids: clinical and therapeutic implications.	2008-10	18782107
Late development of esophageal stricture following radiation and chemotherapy for small cell carcinoma of the lung: A case report.	2008-09-19	18803839
The impact of generic-only drug benefits on patients' use of inhaled corticosteroids in a Medicare population with asthma.	2008-07-18	18638405
Relative oral corticosteroid-sparing effect of 7 inhaled corticosteroids in chronic asthma: a meta-analysis.	2008-07	18681088
Adrenal suppression and Cushing's syndrome secondary to an interaction between ritonavir and fluticasone: a review of the literature.	2008-07	18459946
Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry.	2008-05-02	18054785
Nebulisation of corticosteroid suspensions and solutions with a beta(2) agonist.	2008-05	18416936
New treatment options in allergic rhinitis: patient considerations and the role of ciclesonide.	2008-04	18728855
Intranasal flunisolide treatment in children with adenoidal hypertrophy.	2008-01-09	18179756
Pharmacokinetics and tolerability (Study 1) with particular reference to ocular safety (Study 2) of tiotropium Respimat soft mist inhaler: findings from two dose-ranging studies in healthy men.	2008	18990967
A reappraisal of the clinical efficacy of nebulized flunisolide in pediatric asthma: the Italian experience.	2007-09-22	17883883
Compressor/nebulizers differences in the nebulization of corticosteroids. The CODE study (Corticosteroids and Devices Efficiency).	2007-09-20	17876957
Human receptor kinetics and lung tissue retention of the enhanced-affinity glucocorticoid fluticasone furoate.	2007-07-25	17650349
Strength and endurance of the respiratory and handgrip muscles after the use of flunisolide in normal subjects.	2007-07	17509852
Montelukast in the management of allergic rhinitis.	2007-06	18360641
Hypertrichosis as a side effect of inhaled steroids in children.	2007-04	17351929
Evidence-based selection of inhaled corticosteroid for treatment of chronic asthma.	2007-03-17	17365197
Topical nasal steroids for intermittent and persistent allergic rhinitis in children.	2007-01-24	17253485
A dose-ranging study of tiotropium delivered via Respimat Soft Mist Inhaler or HandiHaler in COPD patients.	2007	18268929
Allergic rhinitis: evidence for impact on asthma.	2006-11-30	17140422
Topical glucocorticosteroids in rhinitis: clinical aspects.	2006-10	16923704
Meta-analysis finds use of inhaled corticosteroids during pregnancy safe: a systematic meta-analysis review.	2006-08	16937916
Once-daily intranasal corticosteroids for allergic rhinitis. Examining Treatment issues.	2006-04	16972477
Alternating current electrical stimulation enhanced chemotherapy: a novel strategy to bypass multidrug resistance in tumor cells.	2006-03-17	16545134
Ciclesonide for the treatment of asthma.	2006-03	18360579
Effects of long-term inhaled corticosteroids on adrenal function in patients with asthma.	2006-03	16597078
Inhaled flunisolide suppresses the hypothalamic-pituitary-adrenocortical axis, but has minimal systemic immune effects in healthy cats.	2006-02-25	16496924
Budesonide/formoterol and formoterol provide similar rapid relief in patients with acute asthma showing refractoriness to salbutamol.	2006-01-24	16433920
Use of Respimat Soft Mist inhaler in COPD patients.	2006	18046862
Pharmacological treatment of chronic obstructive pulmonary disease.	2006	18044097
Nebulized drug admixtures: effect on aerosol characteristics and albuterol output.	2006	17196077
Flunisolide decreases exhaled nitric oxide and nitrotyrosine levels in asthmatic children.	2006	17047290
Flunisolide attenuates nitric oxide-induced DNA damage in rat trachea epithelial cells.	2006	16696591
Efficacy of nebulized flunisolide combined with salbutamol and ipratropium bromide in stable patients with moderate-to-severe chronic obstructive pulmonary disease.	2006	16293958
How do topical nasal corticosteroids improve sleep and daytime somnolence in allergic rhinitis?	2005-12	16337455
Evidence of remodeling in peripheral airways of patients with mild to moderate asthma: effect of hydrofluoroalkane-flunisolide.	2005-11	16275364
Effects of drug treatment on inflammation and hyperreactivity of airways and on immune variables in cats with experimentally induced asthma.	2005-07	16111148
The nitrosterols--a step forward from the steroid anti-inflammatory drugs?	2005-07	16022571
Polymorphisms in signal transducer and activator of transcription 3 and lung function in asthma.	2005-06-03	15935090
Effects of inhaled corticosteroids on bone.	2005-01	15702810
Comparison of the analysis of corticosteroids using different techniques.	2005-01	15700162
[Hydrofluoroalkane as a propellant for pressurized metered-dose inhalers: history, pulmonary deposition, pharmacokinetics, efficacy and safety].	2004-12-29	15622419
Quantitative, highly sensitive liquid chromatography-tandem mass spectrometry method for detection of synthetic corticosteroids.	2004-12	15486026
Add-on therapy options in asthma not adequately controlled by inhaled corticosteroids: a comprehensive review.	2004-10-27	15509300
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.	2004-09	15291899
Significant receptor affinities of metabolites and a degradation product of mometasone furoate.	2004-07-22	15285788
[Therapeutic effect of the association between pulmonary ventilation and aerosol--inhalation with sulphureous mineral water in the chronic bronchopneumopathies].	2004-04	15354759
Asthma steroid pharmacogenetics: a study strategy to identify replicated treatment responses.	2004	16113459
Safety and tolerability of treatments for allergic rhinitis in children.	2004	15366976

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 Created by `admin` on `Mon Mar 31 18:00:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:00:53 GMT 2025`
Record UNII	QK4DYS664X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PREGNA-1,4-DIENE-3,20-DIONE, 6-FLUORO-11,21-DIHYDROXY-16,17-((1-METHYLETHYLIDENE)BIS(OXY))-, HYDRATE (2:1), (6.ALPHA.,11.BETA.,16.ALPHA.)-

Preferred Name

English

FLUNISOLIDE

Official Name

English

AEROSPAN

Brand Name

English

AEROBID

Brand Name

English

FLUNISOLIDE [ORANGE BOOK]

Common Name

English

NASAREL

Brand Name

English

RS-3999

Code

English

FLUNISOLIDE [JAN]

Common Name

English

NASALIDE

Brand Name

English

6?-Fluoro-11?,16?,17,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone, hemihydrate

Common Name

English

Flunisolide hemihydrate [WHO-DD]

Common Name

English

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

Common Name

English

FLUNISOLIDE [VANDF]

Common Name

English

FLUNISOLIDE [MART.]

Common Name

English

NSC-757871

Code

English

FLUNISOLIDE [USAN]

Common Name

English

FLUNISOLIDE [USP MONOGRAPH]

Common Name

English

FLUNISOLIDE [USP-RS]

Common Name

English

Classification Tree Code System Code

WHO-VATC

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