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Identification
NameFlunisolide
Accession NumberDB00180  (APRD00976)
Typesmall molecule
Groupsapproved, investigational
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
SynonymsNot Available
SaltsNot Available
Brand names
NameCompany
AeroBidNot Available
BronalideNot Available
NasalideNot Available
NasarelNot Available
RhinalarNot Available
SyntarisNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number3385-03-3
WeightAverage: 434.4977
Monoisotopic: 434.210466929
Chemical FormulaC24H31FO6
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassGluco/mineralocorticoids, Progestogins and Derivatives
Direct parentGluco/mineralocorticoids, Progestogins and Derivatives
Alternative parentsHalogenated Steroids; Hydroxysteroids; Ketosteroids; Cyclohexanols; 1,3-Dioxolanes; Cyclic Alcohols and Derivatives; Ketones; Primary Alcohols; Polyamines; Enolates; Acetals; Alkyl Fluorides; Aldehydes; Organofluorides
Substituents20-keto-steroid; 6-halo-steroid; 11-hydroxy-steroid; 3-keto-steroid; cyclohexanol; meta-dioxolane; cyclic alcohol; ketone; secondary alcohol; primary alcohol; acetal; polyamine; enolate; ether; carbonyl group; organofluoride; alkyl halide; alkyl fluoride; aldehyde; organohalogen; alcohol
Classification descriptionThis compound belongs to the gluco/mineralocorticoids, progestogins and derivatives. These are steroids whose structure is based on an hydroxylated prostane moiety.
Pharmacology
IndicationFor the maintenance treatment of asthma as a prophylactic therapy.
PharmacodynamicsFlunisolide 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 actionFlunisolide 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.
AbsorptionAbsorbed rapidly
Volume of distributionNot Available
Protein bindingApproximately 40% after oral inhalation
Metabolism

Primarily hepatic, converted to the S beta-OH metabolite.

Route of eliminationNot Available
Half life1.8 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9865
Blood Brain Barrier + 0.9683
Caco-2 permeable + 0.5
P-glycoprotein substrate Substrate 0.7912
P-glycoprotein inhibitor I Non-inhibitor 0.5674
P-glycoprotein inhibitor II Non-inhibitor 0.8383
Renal organic cation transporter Non-inhibitor 0.8304
CYP450 2C9 substrate Non-substrate 0.8679
CYP450 2D6 substrate Non-substrate 0.8856
CYP450 3A4 substrate Substrate 0.6964
CYP450 1A2 substrate Non-inhibitor 0.9327
CYP450 2C9 substrate Non-inhibitor 0.9394
CYP450 2D6 substrate Non-inhibitor 0.9559
CYP450 2C19 substrate Non-inhibitor 0.9311
CYP450 3A4 substrate Non-inhibitor 0.8309
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8806
Ames test Non AMES toxic 0.7682
Carcinogenicity Non-carcinogens 0.9174
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.7033 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9838
hERG inhibition (predictor II) Non-inhibitor 0.671
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
FormRouteStrength
SprayNasal
Spray, meteredNasal
Prices
Unit descriptionCostUnit
Aerobid 250 mcg/act Aerosol 7 gm Inhaler101.95USDinhaler
Aerobid-M 250 mcg/act Aerosol 7 gm Inhaler101.95USDinhaler
Flunisolide 29 mcg/act Solution 25ml Bottle57.16USDbottle
Flunisolide 0.025% Solution 25ml Bottle48.35USDbottle
Aerobid aerosol with adapter14.0USDg
Aerobid-m aerosol with adapter14.0USDg
Flunisolide 29 mcg-0.025% spray2.2USDml
Nasarel 29 mcg-0.025% spray1.98USDml
Apo-Flunisolide 0.025 % Spray0.62USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point245 °CNot Available
water solubilityPractically insolubleNot Available
logP1.1Not Available
Predicted Properties
PropertyValueSource
water solubility3.74e-02 g/lALOGPS
logP2.2ALOGPS
logP1.56ChemAxon
logS-4.1ALOGPS
pKa (strongest acidic)13.73ChemAxon
pKa (strongest basic)-2.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count6ChemAxon
hydrogen donor count2ChemAxon
polar surface area93.06ChemAxon
rotatable bond count2ChemAxon
refractivity111.89ChemAxon
polarizability44.88ChemAxon
number of rings5ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Richard E. Jones, Jacquelyn A. Smithers, “Process for preparing flunisolide.” U.S. Patent US4273710, issued July, 1965.

US4273710
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00324
PubChem Compound82153
PubChem Substance46507894
ChemSpider74144
ChEBI5106
ChEMBLCHEMBL1512
Therapeutic Targets DatabaseDAP001046
PharmGKBPA449661
Drug Product Database2239288
RxListhttp://www.rxlist.com/cgi/generic/flunisolide.htm
Drugs.comhttp://www.drugs.com/cdi/flunisolide-spray.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/aer1009.shtml
WikipediaFlunisolide
ATC CodesR01AD04R03BA03
AHFS Codes
  • 52:08.08
PDB EntriesNot Available
FDA labelshow(4.31 MB)
MSDSshow(74.3 KB)
Interactions
Drug Interactions
Drug
TelithromycinTelithromycin 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.
VoriconazoleVoriconazole, 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 InteractionsNot Available

1. Glucocorticoid receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Glucocorticoid receptor P04150 Details

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

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Lexicomp.

1. Corticosteroid-binding globulin

Kind: protein

Organism: Human

Pharmacological action: yes

Components

Name UniProt ID Details
Corticosteroid-binding globulin P08185 Details

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 September 24, 2013 15:06