2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione

• ChemBase编号: 996
• 分子式: C16H12O3
• 平均质量: 252.26468
• 单一同位素质量: 252.07864424
• SMILES: O=C1C(C(=O)c2c1cccc2)c1ccc(OC)cc1
• Canonical SMILES: COc1ccc(cc1)C1C(=O)c2c(C1=O)cccc2
• InChI: InChI=1S/C16H12O3/c1-19-11-8-6-10(7-9-11)14-15(17)12-4-2-3-5-13(12)16(14)18/h2-9,14H,1H3
• InChIKey: XRCFXMGQEVUZFC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione
• IUPAC传统名: anisindione; 2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione
• 商标名: Miradon; Unidone
• 别名: Anisin indandione; Anisindione; 2-(4-Methoxyphenyl)-1H-indene-1,3(2H)-dione; Miradon; 2- p -Anisyl-1,3-indanedione; Anisindione

登记号

• CAS号: 117-37-3
• MDL号: MFCD00176194
• PubChem SID: 160964459; 46504660
• PubChem CID: 2197
• CHEBI ID: 133809
• CHEMBL: 712
• Chemspider ID: 2112
• DrugBank ID: DB01125
• KEGG ID: D07457
• 美国药典/FDA物质标识码: S747T1ERAJ
• 维基百科标题: Anisindione

理论计算性质

JChem

• Acid pKa: 4.504836
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 1.688942
• LogD (pH = 7.4): 0.0026127298
• Log P: 2.723234
• 摩尔折射率: 71.6967 cm^3
• 极化性: 27.33295 Å^3
• 极化表面积: 43.37 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: 2.99
• LOG S: -4.3
• 溶解度: 1.28e-02 g/l

分子性质

理化性质

• 溶解度: 79.8 mg/L
• 疏水性(logP): 2.6

安全信息

• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 作用靶点: Others
• 给药途径: Oral
• 生物活性机理: Clotting-factors; Depletes clotting-factor-IX; Depletes clotting-factor-VII; Depletes clotting-factor-X; Depletes prothrombin; Interferes with synthesis of vitamin-K-dependent

产品相关信息

• 成盐信息: Free Base
• 简要说明: Tautomers
• 应用领域: Orally active anticoagulant

详细说明

DrugBank - DB01125

• Drug Groups: approved
• Description: Anisindione is a synthetic anticoagulant and an indanedione derivative. It prevents the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, in the liver by inhibiting the vitamin K-mediated gamma-carboxylation of precursor proteins.
• Indication: For the prophylaxis and treatment of venous thrombosis and its extension, the treatment of atrial fibrillation with embolization, the prophylaxis and treatment of pulmonary embolism, and as an adjunct in the treatment of coronary occlusion.
• Pharmacology: Anisindione is a synthetic anticoagulant and an indanedione derivative. It is prescribed only if you cannot take coumarin-type anticoagulants such as coumadin as anisindione is a powerful drug with serious potential side effects. Anticoagulants decrease the clotting ability of the blood and therefore help to prevent harmful clots from forming in the blood vessels. These medicines are sometimes called blood thinners, although they do not actually thin the blood. They also will not dissolve clots that already have formed, but they may prevent the clots from becoming larger and causing more serious problems.
• Toxicity: An overdose is likely to cause abnormal bleeding, for which the symptoms include: bleeding from gums or nose, blood in urine or stools, excessive bleeding from minor cuts, patches of discoloration or bruises on the skin.
• Affected Organisms: Humans and other mammals
• Absorption: Accumulation does not occur with repeated dosing.
• Half Life: Not Known
• Protein Binding: Not Known
• References: CONNELL WF, MAYER GA: Evaluation of anticoagulant therapy with anisindione (miradon). Can Med Assoc J. 1959 May 15;80(10):785-90. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• CONNELL WF, MAYER GA: Evaluation of anticoagulant therapy with anisindione (miradon). Can Med Assoc J. 1959 May 15;80(10):785-90. Pubmed
• Horeau, A. et al., Bull. Soc. Chim. Fr., 1948, 53
• Molho, D. et al., C. R. Hebd. Seances Acad. Sci., 1961, 252, 336, (pharmacol)
• Perjessy, A. et al., Tetrahedron, 1971, 27, 6154, (nmr)
• Pisarenko, L.M. et al., Dokl. Akad. Nauk SSSR, 1973, 213, 638, (nmr)
• Nauta, W.Th. et al., Pharmacochemistry of 1,3-Indandiones, Elsevier, Amsterdam, 1981, 187, (pharmacol, rev)
• Murthy, A.R. et al., J. Med. Chem., 1985, 28, 1591, (synth)
• Grosset, A.B.M. et al., Am. J. Hematol., 1994, 46, 138, (use)
• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 825