2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate

• ChemBase编号: 545
• 分子式: C27H36F2O6
• 平均质量: 494.5679464
• 单一同位素质量: 494.24799531
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](O)([C@@H](C3)C)C(=O)COC(=O)C(C)(C)C)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)COC(=O)C(C)(C)C)C)C)C
• InChI: InChI=1S/C27H36F2O6/c1-14-9-16-17-11-19(28)18-10-15(30)7-8-24(18,5)26(17,29)20(31)12-25(16,6)27(14,34)21(32)13-35-22(33)23(2,3)4/h7-8,10,14,16-17,19-20,31,34H,9,11-13H2,1-6H3/t14-,16+,17+,19+,20+,24+,25+,26+,27+/m1/s1
• InChIKey: JWRMHDSINXPDHB-OJAGFMMFSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate; 2-[(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate
• IUPAC传统名: flumethasone pivalate
• 商标名: Locorten
• 别名: Flumethasone Pivalate; (6α,11β,16α)-21-(2,2-Dimethyl-1-oxopropoxy)-6,9-difluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione; Flumetasone Pivalate; Locacorten; Locorten; Lorinden; Losalen; NSC 107680; Flumethasone 21-Pivalate; 6α,9-Difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-(2,2-dimethylpropionate); Flumethasone pivalate

登记号

• CAS号: 2002-29-1
• EC号: 217-901-1
• MDL号: MFCD00079287
• PubChem SID: 160964008; 46505121; 24894735
• PubChem CID: 443980

理论计算性质

JChem

• Acid pKa: 12.435035
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): 3.5825121
• LogD (pH = 7.4): 3.5825083
• Log P: 3.5825121
• 摩尔折射率: 125.1702 cm^3
• 极化性: 48.730103 Å^3
• 极化表面积: 100.9 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.21
• LOG S: -4.67
• 溶解度: 1.07e-02 g/l

分子性质

理化性质

• 溶解度: 0.392 mg/L
• 疏水性(logP): 2.1

安全信息

• RTECS编号: TU3832010
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 40
• 安全公开号: 22-36
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H351
• GHS警示性声明: P281
• 个人保护装置: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

详细说明

DrugBank - DB00663

• Drug Groups: approved
• Description: Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.
• Indication: For the treatment of contact dermatitis, atopic dermatitis, exczema, psoriasis, diaper rash and other skin conditions
• Pharmacology: Flumethasone pivalate is a moderately potent difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. As it is a privalate salt, its anti-inflammatory action is concentrated at the site of application. This local effect on diseased areas results in a prompt decrease in inflammation, exudation and itching.
• Toxicity: Can lead to signs of irritation such as burning sensation, itching or skin rash at the site of application; hypersensitivity reactions.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic
• Absorption: Minimal if applied topically

Sigma Aldrich - F0891

Application
Flumethasone pivalate is a topical corticosteroid. Prompt decrease in inflammation, exudation and itching is experienced after application. It is a difluorinated corticosteroid ester with anti-inflammatory, antipruritic and vasoconstrictive properties. It is used to study adrenocortical suppression1, plasma transcortin binding, and cutaneous atrophy and telangiectasia2.
Biochem/physiol Actions
Flumethasone is a glucocorticoid receptor agonist. It binds to the nucleus causing a variety of genetic activation and repressions. The anti-inflammatory actions of flumethasone is thought to involve lipocortins and phospholipase A2 inhibitory proteins, which results in the inhibition of arachidonic acid and the control of prostaglandin and leukotriene biosynthesis. Flumethasone suppresses the immune system 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.
Flumethasone pivalate is a glucocorticoid receptor agonist used in studies on plasma transcortin binding.

Toronto Research Chemicals - F455015

An anti-inflammatory anti-itching corticosteroid found in topical creams.

参考文献

• Fliri, A., et al.: J. Med. Chem., 52, 8038 (2009)
• Hoeller, S., et al.: J. Pharm. Sci., 98, 2686 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)