(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

• ChemBase ID: 65
• Molecular Formular: C24H31FO6
• Molecular Mass: 434.4977432
• Monoisotopic Mass: 434.21046693
• SMILES: F[C@H]1C[C@H]2[C@H]3[C@@]([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)(C[C@H](O)[C@@H]2[C@@]2(C1=CC(=O)C=C2)C)C
• Canonical SMILES: OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@H]2[C@H]1C[C@@H](C1=CC(=O)C=C[C@]21C)F)(C)C
• 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
• InChIKey: XSFJVAJPIHIPKU-XWCQMRHXSA-N

NAMES AND DATABASE IDS

Names

• 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,^8.0^1^3,^1^8]icosa-14,17-dien-16-one; (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
• IUPAC Traditional name: soluzione; flunisolide
• Brand Name: Aerobid; Bronalide; Lunis; Nasalide; Nasarel; Rhinalar; Synaclyn; Syntaris
• Synonyms: (6α,11β,16α)-6-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione; 6α-Fluoro-11β,21-dihydroxy-16α,17α-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione; Aerobid M; Bronalide; Lunis; Nisolid; RS 3999; Rhinalar; Soluzione; Synaclyn; Syntaris; Flunisolide [anhydrous]; flunisolide; Flunisolide; AeroBid; Nasalide; Nasarel

Database IDs

• CAS Number: 3385-03-3
• PubChem SID: 160963528; 46507894
• PubChem CID: 82153

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.726746
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.5607916
• LogD (pH = 7.4): 1.5607915
• Log P: 1.5607916
• Molar Refractivity: 111.8852 cm^3
• Polarizability: 43.367012 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -4.07
• Solubility (Water): 3.74e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Practically insoluble
• Apperance: White Solid
• Melting Point: 237-240°C (dec.)
• Hydrophobicity(logP): 1.1

Safety Information

• Storage Condition: -20°C; Refrigerator

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00180

• Drug Groups: approved; 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.
• Indication: For the maintenance treatment of asthma as a prophylactic therapy.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, converted to the S beta-OH metabolite.
• Absorption: Absorbed rapidly
• Half Life: 1.8 hours
• Protein Binding: Approximately 40% after oral inhalation
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1513

Research Area: Inflammation
Biological Activity:
Flunisolide (AeroBid, Nasalide, Nasarel) is a corticosteroid often prescribed as treatment for allergic rhinitis. The principal mechanism of action of Flunisolide is to activate glucocorticoid receptors. It also has anti-inflammatory action. [1]

Toronto Research Chemicals - F500485

Synthetic fluorinated corticosteroid related to Prednisolone (P703740). Antiasthmatic.

REFERENCES

• http://en.wikipedia.org/wiki/Flunisolide
• Chu, N.I., et al.: Drug Metab. Dispos., 7, 81 (1979)
• Pakes, G.E., et al.: Drugs, 19, 397 (1979)