(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编号: 65
• 分子式: C24H31FO6
• 平均质量: 434.4977432
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: soluzione; flunisolide
• 商标名: Aerobid; Bronalide; Lunis; Nasalide; Nasarel; Rhinalar; Synaclyn; Syntaris
• 别名: (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

登记号

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

理论计算性质

JChem

• Acid pKa: 13.726746
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 1.5607916
• LogD (pH = 7.4): 1.5607915
• Log P: 1.5607916
• 摩尔折射率: 111.8852 cm^3
• 极化性: 43.367012 Å^3
• 极化表面积: 93.06 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.2
• LOG S: -4.07
• 溶解度: 3.74e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; Methanol; Practically insoluble
• 外观: White Solid
• 熔点: 237-240°C (dec.)
• 疏水性(logP): 1.1

安全信息

• 保存条件: -20°C; Refrigerator

产品相关信息

• 成盐信息: Free Base

详细说明

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.

参考文献

• 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)