(1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase编号: 209
• 分子式: C22H29FO4
• 平均质量: 376.4616632
• 单一同位素质量: 376.20498763
• SMILES: F[C@@]12[C@H]([C@H]3[C@@]([C@](O)(CC3)C(=O)C)(C[C@@H]1O)C)C[C@@H](C1=CC(=O)C=C[C@]21C)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](C)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1CC[C@]2(O)C(=O)C)C)C
• InChI: InChI=1S/C22H29FO4/c1-12-9-17-15-6-8-21(27,13(2)24)20(15,4)11-18(26)22(17,23)19(3)7-5-14(25)10-16(12)19/h5,7,10,12,15,17-18,26-27H,6,8-9,11H2,1-4H3/t12-,15-,17-,18-,19-,20-,21-,22-/m0/s1
• InChIKey: FAOZLTXFLGPHNG-KNAQIMQKSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one; (1R,2S,8S,10S,11S,14R,15S,17S)-14-acetyl-1-fluoro-14,17-dihydroxy-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC传统名: fluorometholone
• 商标名: Cortilet; Delmeson; Efflumidex; FML Liquifilm; Flarex; Fluaton; Flumetholon; Fluor-op; FML Forte; Loticort; Oxylone; Trilcin; Ursnon
• 别名: 11β,17α-Dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,20-dione; Fluorometholone; (6α,11β)-9-Fluoro-11,17-dihydroxy-6-methylpregna-1,4-diene-3,20-dione; 21-Desoxy-9α-fluoro-6-methylprednisolone; 6α-Methyl-9α-fluoro-11β,17α-dihydroxypregna-1,4-diene-3,20-dione; 6α-Methyl-9α-fluoro-21-desoxyprednisolone; 9α-Fluoro-11β,17α-dihydroxy-6α-methylpregna-1,4-diene-3,20-dione; Cortilet; Delmeson; Efflumidex; FML Forte; FML Liquifilm; FML SOP; Fluaton; Fluaton PVA; Flumetholon; Flumetholone; Fluor-Op; Loticort; NSC-33001; Oxylone; U 8614; Ursnon; FML; Fluoromethalone; Fluormetholone; Fluormetholon; Fluorometholone; 11β, 17α-Dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,-20-dione

登记号

• CAS号: 426-13-1
• EC号: 207-041-5
• MDL号: MFCD00056461
• PubChem SID: 24894996; 160963672; 46505984
• PubChem CID: 9878

理论计算性质

JChem

• Acid pKa: 12.648287
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 2.4208639
• LogD (pH = 7.4): 2.4208615
• Log P: 2.420864
• 摩尔折射率: 100.8677 cm^3
• 极化性: 38.960907 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.34
• LOG S: -4.36
• 溶解度: 1.66e-02 g/l

分子性质

理化性质

• 溶解度: 30 mg/L; DMSO; Methanol
• 外观: White to Off-White Solid
• 熔点: 274-276°C
• 疏水性(logP): 2

安全信息

• 保存条件: -20°C Freezer; Room Temperature (15-30°C), Protect from light
• RTECS编号: TU3834100
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 20/21/22
• 安全公开号: 36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H312-H332
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

产品相关信息

• 纯度: ≥98%

详细说明

MP Biomedicals - 02190208

(11β, 17α-Dihydroxy-9-fluoro-6-methyl-1,4-pregnadiene-3,-20-dione)

DrugBank - DB00324

• Drug Groups: approved
• Description: A glucocorticoid employed, usually as eye drops, in the treatment of allergic and inflammatory conditions of the eye. It has also been used topically in the treatment of various skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p732)
• Indication: For the ophthalmic treatment of corticosteroid-responsive inflammation of the palpebral and bulbar conjunctiva, cornea and anterior segment of the globe.
• Pharmacology: Corticosteroids such as fluorometholone inhibit the inflammatory response to a variety of inciting agents and probably delay or slow healing. They inhibit the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, deposition of collagen, and scar formation associated with inflammation.
• Toxicity: Side effects may include acute anterior uveitis and perforation of the globe. Keratitis, conjunctivitis, corneal ulcers, mydriasis, conjunctival hyperemia, loss of accommodation and ptosis have occasionally been reported following local use of corticosteroids. LD₅₀ = 234 mg/kg (rats)
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - F9381

Biochem/physiol Actions
Clinically significant in allergic conjunctivitis and as anti-inflammatory following cataract surgery.1

Toronto Research Chemicals - F593145

Fluorometholone is a glucocorticoid; anti-inflammatory.

参考文献

• Kupferman, A., et al.: Arch. Ophthlmol., 640, 100 (1982)
• Tokunaga H., et al.: Chem. Pharm. Bull., 32, 4012 (1982)