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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
Synonyms
Flunisolida
Flunisolide anhydrous
Flunisolidum
External Identifiers Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Aerospanaerosol, metered80 ug/1respiratory (inhalation)MEDA Pharmaceuticals2012-03-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Aerospanaerosol, metered80 ug/1respiratory (inhalation)Acton Pharmaceuticals, Inc.2012-03-01Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Bronalide Inhal 250mcg/aemmetered-dose aerosol250 mcginhalationBoehringer Ingelheim (Canada) Ltd Ltee1988-12-311999-02-15Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Novo-flunisolidespray25 mcgnasalNovopharm Limited1998-06-302005-08-10Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
PMS-flunisolidespray0.025 %nasalPharmascience Inc1994-12-312009-08-27Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Ratio-flunisolidespray25 mcgnasalRatiopharm Inc Division Of Teva Canada Limited1993-12-312010-08-02Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhinalarspray.025 %nasalSyntex Inc.1978-12-311996-09-30Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Rhinalar Nasal Mistsolution; spray25 mcgnasalIvax Laboratories Incorporated1996-12-312015-10-26Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-flunisolide Nasal Spraymetered-dose pump0.25 mgnasalApotex Inc2000-03-10Not applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Flunisolidesolution.25 mg/mLnasalBausch & Lomb Incorporated2002-02-20Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flunisolidespray, metered.25 mg/mLnasalRising Pharmaceuticals, Inc2006-08-03Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Flunisolidesolution.25 mg/mLnasalPhysicians Total Care, Inc.2003-05-23Not applicableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AeroBidRoche
BronalideKrewel
NasalideTeva Santé
NasarelNot Available
SyntarisTeva
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIIQK4DYS664X
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[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassHydroxysteroids
Direct Parent21-hydroxysteroids
Alternative Parents
Substituents
  • 21-hydroxysteroid
  • Progestogin-skeleton
  • Pregnane-skeleton
  • 20-oxosteroid
  • 11-hydroxysteroid
  • 11-beta-hydroxysteroid
  • Oxosteroid
  • Halo-steroid
  • 6-halo-steroid
  • 3-oxosteroid
  • 3-oxo-delta-1,4-steroid
  • Delta-1,4-steroid
  • Cyclic alcohol
  • Alpha-hydroxy ketone
  • Meta-dioxolane
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+0.9865
Blood Brain Barrier+0.9683
Caco-2 permeable+0.5
P-glycoprotein substrateSubstrate0.7912
P-glycoprotein inhibitor INon-inhibitor0.5674
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.8304
CYP450 2C9 substrateNon-substrate0.8679
CYP450 2D6 substrateNon-substrate0.8856
CYP450 3A4 substrateSubstrate0.6964
CYP450 1A2 substrateNon-inhibitor0.9327
CYP450 2C9 inhibitorNon-inhibitor0.9394
CYP450 2D6 inhibitorNon-inhibitor0.9559
CYP450 2C19 inhibitorNon-inhibitor0.9311
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8806
Ames testNon AMES toxic0.7682
CarcinogenicityNon-carcinogens0.9174
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7033 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9838
hERG inhibition (predictor II)Non-inhibitor0.671
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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
Aerosol, meteredrespiratory (inhalation)80 ug/1
Metered-dose pumpnasal0.25 mg
Metered-dose aerosolinhalation250 mcg
Solutionnasal.25 mg/mL
Spray, meterednasal.25 mg/mL
Spraynasal0.025 %
Spraynasal25 mcg
Spraynasal.025 %
Solution; spraynasal25 mcg
Prices
Unit descriptionCostUnit
Aerobid 250 mcg/act Aerosol 7 gm Inhaler101.95USD inhaler
Aerobid-M 250 mcg/act Aerosol 7 gm Inhaler101.95USD inhaler
Flunisolide 29 mcg/act Solution 25ml Bottle57.16USD bottle
Flunisolide 0.025% Solution 25ml Bottle48.35USD bottle
Aerobid aerosol with adapter14.0USD g
Aerobid-m aerosol with adapter14.0USD g
Flunisolide 29 mcg-0.025% spray2.2USD ml
Nasarel 29 mcg-0.025% spray1.98USD ml
Apo-Flunisolide 0.025 % Spray0.62USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point226-230American Cyanamid Co.; British Patent 933,867; August 14, 1963.
water solubilityPractically insolubleNot Available
logP1.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0374 mg/mLALOGPS
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 Area93.06 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity111.89 m3·mol-1ChemAxon
Polarizability44.88 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

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

US4273710
General ReferencesNot Available
External Links
ATC CodesR03BA03R01AD04
AHFS Codes
  • 52:08.08
PDB EntriesNot Available
FDA labelDownload (4.31 MB)
MSDSDownload (74.3 KB)
Interactions
Drug Interactions
Drug
Amphotericin BFlunisolide may increase the hypokalemic activities of Amphotericin B.
AprepitantThe serum concentration of Flunisolide can be increased when it is combined with Aprepitant.
AtazanavirThe serum concentration of Flunisolide can be increased when it is combined with Atazanavir.
BendroflumethiazideFlunisolide may increase the hypokalemic activities of Bendroflumethiazide.
BexaroteneThe serum concentration of Flunisolide can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Flunisolide can be increased when it is combined with Boceprevir.
BosentanThe serum concentration of Flunisolide can be decreased when it is combined with Bosentan.
BumetanideFlunisolide may increase the hypokalemic activities of Bumetanide.
CarbamazepineThe metabolism of Flunisolide can be increased when combined with Carbamazepine.
CeritinibFlunisolide may increase the hyperglycemic activities of Ceritinib.
ChlorothiazideFlunisolide may increase the hypokalemic activities of Chlorothiazide.
ChlorthalidoneFlunisolide may increase the hypokalemic activities of Chlorthalidone.
ClarithromycinThe serum concentration of Flunisolide can be increased when it is combined with Clarithromycin.
CobicistatThe serum concentration of Flunisolide can be increased when it is combined with Cobicistat.
ConivaptanThe serum concentration of Flunisolide can be increased when it is combined with Conivaptan.
CrizotinibThe metabolism of Flunisolide can be decreased when combined with Crizotinib.
DabrafenibThe serum concentration of Flunisolide can be decreased when it is combined with Dabrafenib.
DarunavirThe serum concentration of Flunisolide can be increased when it is combined with Darunavir.
DasatinibThe serum concentration of Flunisolide can be increased when it is combined with Dasatinib.
DeferasiroxThe serum concentration of Flunisolide can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Flunisolide can be decreased when combined with Delavirdine.
DexamethasoneThe serum concentration of Flunisolide can be decreased when it is combined with Dexamethasone.
DiltiazemThe metabolism of Flunisolide can be decreased when combined with Diltiazem.
DronedaroneThe metabolism of Flunisolide can be decreased when combined with Dronedarone.
EfavirenzThe serum concentration of Flunisolide can be decreased when it is combined with Efavirenz.
EnzalutamideThe metabolism of Flunisolide can be increased when combined with Enzalutamide.
ErythromycinThe metabolism of Flunisolide can be decreased when combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Flunisolide can be decreased when it is combined with Eslicarbazepine acetate.
Ethacrynic acidFlunisolide may increase the hypokalemic activities of Ethacrynic acid.
EtravirineThe serum concentration of Flunisolide can be decreased when it is combined with Etravirine.
FluconazoleThe metabolism of Flunisolide can be decreased when combined with Fluconazole.
FosamprenavirThe metabolism of Flunisolide can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Flunisolide can be increased when it is combined with Fosaprepitant.
FosphenytoinThe metabolism of Flunisolide can be increased when combined with Fosphenytoin.
FurosemideFlunisolide may increase the hypokalemic activities of Furosemide.
HydrochlorothiazideFlunisolide may increase the hypokalemic activities of Hydrochlorothiazide.
IdelalisibThe serum concentration of Flunisolide can be increased when it is combined with Idelalisib.
ImatinibThe metabolism of Flunisolide can be decreased when combined with Imatinib.
IndapamideFlunisolide may increase the hypokalemic activities of Indapamide.
IndinavirThe serum concentration of Flunisolide can be increased when it is combined with Indinavir.
IsavuconazoniumThe metabolism of Flunisolide can be decreased when combined with Isavuconazonium.
ItraconazoleThe serum concentration of Flunisolide can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Flunisolide can be increased when it is combined with Ivacaftor.
KetoconazoleThe serum concentration of Flunisolide can be increased when it is combined with Ketoconazole.
LopinavirThe serum concentration of Flunisolide can be increased when it is combined with Lopinavir.
LuliconazoleThe serum concentration of Flunisolide can be increased when it is combined with Luliconazole.
MethyclothiazideFlunisolide may increase the hypokalemic activities of Methyclothiazide.
MetolazoneFlunisolide may increase the hypokalemic activities of Metolazone.
MifepristoneThe serum concentration of Flunisolide can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of Flunisolide can be decreased when it is combined with Mitotane.
ModafinilThe serum concentration of Flunisolide can be decreased when it is combined with Modafinil.
NadololFlunisolide may increase the hypokalemic activities of Nadolol.
NafcillinThe serum concentration of Flunisolide can be decreased when it is combined with Nafcillin.
NefazodoneThe serum concentration of Flunisolide can be increased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Flunisolide can be increased when it is combined with Nelfinavir.
NetupitantThe serum concentration of Flunisolide can be increased when it is combined with Netupitant.
NilotinibThe metabolism of Flunisolide can be decreased when combined with Nilotinib.
OsimertinibThe serum concentration of Flunisolide can be increased when it is combined with Osimertinib.
PalbociclibThe serum concentration of Flunisolide can be increased when it is combined with Palbociclib.
PalonosetronThe serum concentration of Flunisolide can be increased when it is combined with Palonosetron.
PhenobarbitalThe metabolism of Flunisolide can be increased when combined with Phenobarbital.
PhenytoinThe metabolism of Flunisolide can be increased when combined with Phenytoin.
PosaconazoleThe serum concentration of Flunisolide can be increased when it is combined with Posaconazole.
PrimidoneThe metabolism of Flunisolide can be increased when combined with Primidone.
RifabutinThe metabolism of Flunisolide can be increased when combined with Rifabutin.
RifampicinThe metabolism of Flunisolide can be increased when combined with Rifampicin.
RifapentineThe metabolism of Flunisolide can be increased when combined with Rifapentine.
RitonavirThe serum concentration of Flunisolide can be increased when it is combined with Ritonavir.
SaquinavirThe serum concentration of Flunisolide can be increased when it is combined with Saquinavir.
SiltuximabThe serum concentration of Flunisolide can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Flunisolide can be increased when it is combined with Simeprevir.
StiripentolThe serum concentration of Flunisolide can be increased when it is combined with Stiripentol.
SulfisoxazoleThe metabolism of Flunisolide can be decreased when combined with Sulfisoxazole.
TelaprevirThe serum concentration of Flunisolide can be increased when it is combined with Telaprevir.
TelithromycinThe serum concentration of Flunisolide can be increased when it is combined with Telithromycin.
TocilizumabThe serum concentration of Flunisolide can be decreased when it is combined with Tocilizumab.
TorasemideFlunisolide may increase the hypokalemic activities of Torasemide.
VerapamilThe metabolism of Flunisolide can be decreased when combined with Verapamil.
VoriconazoleThe serum concentration of Flunisolide can be increased when it is combined with Voriconazole.
Food InteractionsNot Available

Targets

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

Enzymes

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.

Carriers

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
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Drug created on June 13, 2005 07:24 / Updated on September 24, 2013 15:06