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Identification
Name Flunisolide
Accession Number DB00180 (APRD00976)
Type small molecule
Groups approved
Description

Flunisolide (marketed as AeroBid, Nasalide, Nasarel) is a corticosteroid often prescribed as treatment for allergic rhinitis.

The principle mechanism of action of flunisolide is to activate glucocorticoid receptors. It also has anti-inflammatory action.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Flunisolide [anhydrous]
Salts Not Available
Brand names
Name Company
Aerobid
Bronalide
Lunis
Nasalide
Nasarel
Rhinalar
Synaclyn
Syntaris
Brand mixtures Not Available
Categories
  • Anti-Asthmatic Agents
  • Anti-inflammatory Agents
CAS number 3385-03-3
Weight Average: 434.4977
Monoisotopic: 434.210466929
Chemical Formula C24H31FO6
InChI Key InChIKey=XSFJVAJPIHIPKU-XWCQMRHXSA-N
InChI
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
Plain Text
IUPAC Name
(1S,2S,4R,8S,9S,11S,12S,13R,19S)-19-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetals and Derivatives
  • Alkyl Halides
  • Ethers
  • Dioxoles
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Ketones
Pharmacology
Indication For the maintenance treatment of asthma as a prophylactic therapy.
Pharmacodynamics 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.
Mechanism of action 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.
Absorption Absorbed rapidly
Volume of distribution Not Available
Protein binding Approximately 40% after oral inhalation
Metabolism Primarily hepatic, converted to the S beta-OH metabolite.
Route of elimination Not Available
Half life 1.8 hours
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Roche palo alto llc
  • Acton pharmaceuticals inc
  • Apotex inc richmond hill
  • Bausch and lomb pharmaceuticals inc
  • Qpharma llc
  • Ivax research inc
  • Teva branded pharmaceutical products r and d inc
Packagers
Dosage forms
Form Route Strength
Spray Nasal
Spray, metered Nasal
Prices
Unit description Cost Unit
Aerobid 250 mcg/act Aerosol 7 gm Inhaler 101.95 USD inhaler
Aerobid-M 250 mcg/act Aerosol 7 gm Inhaler 101.95 USD inhaler
Flunisolide 29 mcg/act Solution 25ml Bottle 57.16 USD bottle
Flunisolide 0.025% Solution 25ml Bottle 48.35 USD bottle
Aerobid aerosol with adapter 14.0 USD g
Aerobid-m aerosol with adapter 14.0 USD g
Flunisolide 29 mcg-0.025% spray 2.2 USD ml
Nasarel 29 mcg-0.025% spray 1.98 USD ml
Apo-Flunisolide 0.025 % Spray 0.62 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 245 °C Not Available
water solubility Practically insoluble Not Available
logP 1.1 Not Available
Predicted Properties
Property Value Source
water solubility 3.74e-02 g/l ALOGPS
logP 2.2 ALOGPS
logP 1.56 ChemAxon
logS -4.1 ALOGPS
pKa (strongest acidic) 13.73 ChemAxon
pKa (strongest basic) -2.9 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 6 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 93.06 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 111.89 ChemAxon
polarizability 44.88 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00324 Link_out
PubChem Compound 82153 Link_out
PubChem Substance 46507894 Link_out
ChemSpider 74144 Link_out
ChEBI 5106 Link_out
ChEMBL 5106 Link_out
Therapeutic Targets Database DAP001046 Link_out
PharmGKB PA449661 Link_out
Drug Product Database 2239288 Link_out
RxList http://www.rxlist.com/cgi/generic/flunisolide.htm Link_out
Drugs.com http://www.drugs.com/cdi/flunisolide-spray.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/aer1009.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Flunisolide Link_out
ATC Codes
  • R01AD04
  • R03BA03
AHFS Codes
  • 52:08.08
PDB Entries Not Available
FDA label show (4.31 MB)
MSDS show (74.3 KB)
Interactions
Drug Interactions
Drug Interaction
Telithromycin Telithromycin may reduce clearance of Flunisolide. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Flunisolide if Telithromycin is initiated, discontinued or dose changed.
Voriconazole Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of flunisolide by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of flunisolide if voriconazole is initiated, discontinued or dose changed.
Food Interactions Not Available
Targets

1. Glucocorticoid receptor

Pharmacological action: yes
Actions: agonist

Receptor for glucocorticoids (GC). Has a dual mode of action:as a transcription factor that binds to glucocorticoid response elements (GRE) and as a modulator of other transcription factors. Affects inflammatory responses, cellular proliferation and differentiation in target tissues. Could act as a coactivator for STAT5-dependent transcription upon growth hormone (GH) stimulation and could reveal an essential role of hepatic GR in the control of body growth

Organism class: human
UniProt ID: P04150 Link_out
Gene: NR3C1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Hochhaus G, Moellmann HW: Binding affinities of rimexolone (ORG 6216), flunisolide and their putative metabolites for the glucocorticoid receptor of human synovial tissue. Agents Actions. 1990 Jun;30(3-4):377-80. Pubmed
  2. Johnson M: Development of fluticasone propionate and comparison with other inhaled corticosteroids. J Allergy Clin Immunol. 1998 Apr;101(4 Pt 2):S434-9. Pubmed
  3. Valotis A, Hogger P: Significant receptor affinities of metabolites and a degradation product of mometasone furoate. Respir Res. 2004 Jul 22;5:7. Pubmed
  4. Hogger P, Erpenstein U, Rohdewald P, Sorg C: Biochemical characterization of a glucocorticoid-induced membrane protein (RM3/1) in human monocytes and its application as model system for ranking glucocorticoid potency. Pharm Res. 1998 Feb;15(2):296-302. Pubmed
  5. Badia L, Lund V: Topical corticosteroids in nasal polyposis. Drugs. 2001;61(5):573-8. Pubmed
  6. Philibert D, Bouchoux F, Cerede E, Corallo F, Allaire JM: [Pharmacologic study of the glucocorticoid activity of flunisolide compared with other steroids in the rat] Allerg Immunol (Paris). 1993 Feb;25(2):77-81. Pubmed
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: substrate

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out
Carriers

1. Corticosteroid-binding globulin

Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species

UniProt ID: P08185 Link_out
Gene: SERPINA6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19