2-phenyl-2,3-dihydro-1H-indene-1,3-dione

• ChemBase ID: 381
• Molecular Formular: C15H10O2
• Molecular Mass: 222.2387
• Monoisotopic Mass: 222.06807956
• SMILES: O=C1C(C(=O)c2c1cccc2)c1ccccc1
• Canonical SMILES: O=C1C(c2ccccc2)C(=O)c2c1cccc2
• InChI: InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H
• InChIKey: NFBAXHOPROOJAW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-phenyl-2,3-dihydro-1H-indene-1,3-dione
• IUPAC Traditional name: phenindione
• Brand Name: Athrombon; Bindan; Cronodione; Danedion; Danilon; Danilone; Diadilan; Dindevan; Dineval; Diophindane; Emandion; Emandione; Eridione; Fenhydren; Fenilin; Fenindion; Hedulin; Hemolidione; Indema; Indion; Indon; PID; Phenhydren; Phenillin; Phenylen; Phenylin; Phenylindanedione; Phenylindione; Phenyline; Phenyllin; Pindione; Rectadione; Theradione; Thrombasal; Tromazal; Trombol
• Synonyms: Phenindione; Dindevan; Rectadione; Phenindione; 2-Phenyl-1,3-indandione; 2-phenyl-1H-indene-1,3(2H)-dione; 2-phenylindane-1,3-dione; 2-PHENYL-1,3-INDANEDIONE; 2-phenyl-2,3-dihydro-1H-indene-1,3-dione; 苯茚二酮; 2-苯基-1,3-茚满二酮

Database IDs

• CAS Number: 83-12-5
• EC Number: 201-454-4
• MDL Number: MFCD00003782
• Beilstein Number: 1911699
• PubChem SID: 24898344; 160963844; 46505018
• PubChem CID: 4760
• CHEBI ID: 8066
• ATC CODE: B01AA02
• CHEMBL: 711
• Chemspider ID: 4596
• DrugBank ID: DB00498
• KEGG ID: D08354
• Unique Ingredient Identifier: 5M7Y6274ZE
• Wikipedia Title: Phenindione

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.875343
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.1649199
• LogD (pH = 7.4): 0.43830353
• Log P: 2.8809052
• Molar Refractivity: 65.2335 cm^3
• Polarizability: 24.823254 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.1
• LOG S: -3.98
• Solubility (Water): 2.30e-02 g/l

PROPERTIES

Physical Property

• Solubility: 27 mg/L (at 20 oC)
• Melting Point: 144-148 °C; 144-148 °C(lit.); 148 - 150°C
• Hydrophobicity(logP): 2.6; 2.81

Safety Information

• Storage Condition: -20°C
• RTECS: NK6125000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25; 25-43
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H317
• GHS Precautionary statements: P280-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 5 to 10 hours
• Protein Bound: 88%
• Pregnancy Category: D (Australia); Passes into breast milk

Product Information

• Purity: ≥95.0% (CH); 95%; 97%; null%
• Grade: purum
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C15H10O2

DETAILS

MP Biomedicals - 05216665

MP Biomedicals Rare Chemical collection

DrugBank - DB00498

• Drug Groups: approved
• Description: An indandione that has been used as an anticoagulant. Phenindione has actions similar to warfarin, but it is now rarely employed because of its higher incidence of severe adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p234)
• Indication: For the treatment of pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, mural thrombosis, and thrombophili. Also used for anticoagulant prophylaxis.
• Pharmacology: Phenindione thins the blood by antagonizing vitamin K which is required for the production of clotting factors in the liver. Anticoagulants such as Phenindione have no direct effect on an established thrombus, nor do they reverse ischemic tissue damage (damage caused by an inadequate blood supply to an organ or part of the body). However, once a thrombus has occurred, the goal of anticoagulant treatment is to prevent further extension of the formed clot and prevent secondary thromboembolic complications which may result in serious and possibly fatal sequelae. Phenindione has actions similar to warfarin, but it is now rarely employed because of its higer incidence of severe adverse effects.
• Toxicity: Oral, mouse: LD50 = 175 mg/kg; Oral, rat: LD50 = 163 mg/kg.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Absorbed slowly from the gastrointestinal tract.
• Half Life: 5-10 hours
• Protein Binding: 88%
• References: / [Link]
• External Links: Wikipedia

Selleck Chemicals - S1921

Research Area: Immunology, Cardiovascular Disease
Biological Activity:
Phenindione(Rectadione) is an anticoagulant which functions as a Vitamin K antagonist. A lymphocyte transformation test showed proliferation of T-cells from the hypersensitive patient, but not from four controls on exposure to phenindione in vitro. Drug-specific T-cell clones were generated and characterized in terms of their phenotype, functionality, and mechanism of antigen presentation. Forty-three human leukocyte antigen class II restricted CD4+ αβ T-cell clones were identified. T-cell activation resulted in the secretion of interferon-γ and interleukin-5. [1][2]

Sigma Aldrich - P26406

Packaging
25 g in poly bottle

REFERENCES

• Link/
• Naisbitt DJ et al. J Pharmacol Exp Ther. 2005 Jun