Basic information
- CAS
3385-03-3- Standard SMILES
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(C(=O)CO)O1- InChIKey
XSFJVAJPIHIPKU-XWCQMRHXSA-N- Molecular formula
- C24H31FO6
- Average molar mass
- 434.5 g/mol
- Monoisotopic mass
- 434.21046687
Overview
Flunisolide can cause developmental toxicity and female reproductive toxicity according to state or federal government labeling requirements.
Names & identifiers
- Preferred name
- Flunisolide
- IUPAC
- (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
- English name
- Flunisolide
- Molecular formula
- C24H31FO6
- Molecular weight
- 434.5
Names & synonyms
flunisolide3385-03-3AerobidSyntarisFlunisolide anhydrousFlunisolidaNasalideNasarelAerospanFlunisolidumFlunisolide HemihydrateAerospan HFA
Show more names
6-FLUORO-11,16ALPHA,17,21-TETRAHYDROXYPREGNA-1,4-DIENE-3,20-DIONE 16,17-ACETONIDELunisNisolidRS 3999SynaclynBronalideAerobid M
DTXSID1045534RS-3999Syntaris Hayfever77326-96-678M02AA8KFCHEBI:5106DTXCID9025534NSC-757871
Database identifiers
- CAS
3385-03-3、77326-96-6- PubChem CID
- 82153
- DTXSID
DTXSID1045534- ChEMBL
CHEMBL1512- ChEBI
CHEBI:5106- UNII
- 78M02AA8KF
- EC Number
- 222-193-2、680-658-9
- Nikkaji
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 93.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 2
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 910
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Respiratory system -> Nasal preparations
LogP1.1
Solubility
Practically insoluble
3.74e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Allergic Agents; Anti-Asthmatic Agents; Corticosteroids, Inhaled; Glucocorticoids; Anti-Inflammatory Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Melting Point
226-230
245 °C
Physical DescriptionSolid
Collision Cross Section
219.68 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
199.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (97.7%): Fatal if swallowed [Danger Acute toxicity, oral]
P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 43 reports by companies from 5 notifications to the ECHA C&L Inventory.
Danger
H300 (66.7%): Fatal if swallowed [Danger Acute toxicity, oral]
Hazard information
Regulatory InformationHazard Traits - Developmental Toxicity; Reproductive Toxicity
Hazard Classes and Categories
Acute Tox. 1 (97.7%)
Acute Tox. 1 (66.7%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- TU3900000
- ridadr
- UN 2811 6.1 / PGI
- risk_code
- 28
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- T+
- safety_code
- 28-36/37-45
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
R - Respiratory system
QR - Respiratory system
QR - Respiratory system
Protein BindingApproximately 40% after oral inhalation
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.
Biological Half-Life1.8 hours
Metabolism/MetabolitesPrimarily hepatic, converted to the S beta-OH metabolite.
FDA Pharmacological Classification
78M02AA8KF
FLUNISOLIDE ANHYDROUS
Established Pharmacologic Class [EPC] - Corticosteroid
Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists
Flunisolide anhydrous is a Corticosteroid. The mechanism of action of flunisolide anhydrous is as a Corticosteroid Hormone Receptor Agonist.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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