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
Transcriptional potencies of inhaled glucocorticoids.	2000 Jul	10903220
Topical corticosteroids in nasal polyposis.	2001	11368283
Cost analysis of the use of inhaled corticosteroids in the treatment of asthma: a 1-year follow-up.	2001 Dec	11778798
e-NO peak versus e-NO plateau values in evaluating e-NO production in steroid-naive and in steroid-treated asthmatic children and in detecting response to inhaled steroid treatment.	2001 Jan	11180673
Pharmacokinetics of intranasal corticosteroids.	2001 Jul	11449203
Improved asthma control after changing from low-to-medium doses of other inhaled corticosteroids to low-dose fluticasone propionate.	2001 Jun 8	11549975
Aerosol characterization of nebulized intranasal glucocorticoid formulations.	2001 Summer	11681655
The output of flunisolide from different nebulisers.	2002 Apr	11999135
Clinical review: severe asthma.	2002 Feb	11940264
Single-dose study to compare the pharmacokinetics of HFA flunisolide and CFC flunisolide.	2002 Feb	11835202
Cushing's syndrome, growth impairment, and occult adrenal suppression associated with intranasal steroids.	2002 Jul	12089123
Systemic effect comparisons of six inhaled corticosteroid preparations.	2002 May 15	12016099
Intranasal corticosteroids for allergic rhinitis.	2002 Nov	12432972
Multiple-dose proportionality study of flunisolide hydrofluoroalkane.	2002 Sep-Oct	12476540
Triple inhaled drug protocol for the treatment of acute severe asthma.	2003 Jun	12796167
Significant receptor affinities of metabolites and a degradation product of mometasone furoate.	2004 Jul 22	15285788
Interactions between rhinitis and asthma.	2004 Mar-Apr	15176491
Treatment with inhaled flunisolide.	2004 May	15136418
Add-on therapy options in asthma not adequately controlled by inhaled corticosteroids: a comprehensive review.	2004 Oct 27	15509300
Comparison of the analysis of corticosteroids using different techniques.	2005 Jan	15700162
Polymorphisms in signal transducer and activator of transcription 3 and lung function in asthma.	2005 Jun 3	15935090
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
Meta-analysis finds use of inhaled corticosteroids during pregnancy safe: a systematic meta-analysis review.	2006 Aug	16937916
Allergic rhinitis: evidence for impact on asthma.	2006 Nov 30	17140422
A dose-ranging study of tiotropium delivered via Respimat Soft Mist Inhaler or HandiHaler in COPD patients.	2007	18268929
Strength and endurance of the respiratory and handgrip muscles after the use of flunisolide in normal subjects.	2007 Jul	17509852
Montelukast in the management of allergic rhinitis.	2007 Jun	18360641
Intranasal flunisolide treatment in children with adenoidal hypertrophy.	2007 Oct-Dec	18179756
Molecular and clinical pharmacology of intranasal corticosteroids: clinical and therapeutic implications.	2008 Oct	18782107

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

QR01AD04