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

• ChemBase ID: 996
• Molecular Formular: C16H12O3
• Molecular Mass: 252.26468
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione
• IUPAC Traditional name: anisindione; 2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione
• Brand Name: Miradon; Unidone
• Synonyms: Anisin indandione; Anisindione; 2-(4-Methoxyphenyl)-1H-indene-1,3(2H)-dione; Miradon; 2- p -Anisyl-1,3-indanedione; Anisindione

Database IDs

• CAS Number: 117-37-3
• MDL Number: MFCD00176194
• PubChem SID: 160964459; 46504660
• PubChem CID: 2197
• CHEBI ID: 133809
• CHEMBL: 712
• Chemspider ID: 2112
• DrugBank ID: DB01125
• KEGG ID: D07457
• Unique Ingredient Identifier: S747T1ERAJ
• Wikipedia Title: Anisindione

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.504836
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.688942
• LogD (pH = 7.4): 0.0026127298
• Log P: 2.723234
• Molar Refractivity: 71.6967 cm^3
• Polarizability: 27.33295 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.99
• LOG S: -4.3
• Solubility (Water): 1.28e-02 g/l

PROPERTIES

Physical Property

• Solubility: 79.8 mg/L
• Hydrophobicity(logP): 2.6

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: Others
• Admin Routes: Oral
• Mechanism of Action: Clotting-factors; Depletes clotting-factor-IX; Depletes clotting-factor-VII; Depletes clotting-factor-X; Depletes prothrombin; Interferes with synthesis of vitamin-K-dependent

Product Information

• Salt Data: Free Base
• Description: Tautomers
• Application(s): Orally active anticoagulant

DETAILS

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

REFERENCES

• 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