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83-12-5 molecular structure
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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 and InChIs

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

Cite this record

CBID:381 http://www.chembase.cn/molecule-381.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.875343  H Acceptors
H Donor LogD (pH = 5.5) 2.1649199 
LogD (pH = 7.4) 0.43830353  Log P 2.8809052 
Molar Refractivity 65.2335 cm3 Polarizability 24.823254 Å3
Polar Surface Area 34.14 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.1  LOG S -3.98 
Solubility (Water) 2.30e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
27 mg/L (at 20 oC) expand Show data source
Melting Point
144-148 °C expand Show data source
144-148 °C(lit.) expand Show data source
148 - 150°C expand Show data source
Hydrophobicity(logP)
2.6 expand Show data source
2.81 expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
NK6125000 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
25 expand Show data source
25-43 expand Show data source
Safety Statements
36/37/39-45 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H317 expand Show data source
GHS Precautionary statements
P280-P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Admin Routes
Oral expand Show data source
Half Life
5 to 10 hours expand Show data source
Protein Bound
88% expand Show data source
Pregnancy Category
D (Australia) expand Show data source
Passes into breast milk expand Show data source
Purity
≥95.0% (CH) expand Show data source
95% expand Show data source
97% expand Show data source
null% expand Show data source
Grade
purum expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C15H10O2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05216665 external link
MP Biomedicals Rare Chemical collection
DrugBank - DB00498 external link
Item Information
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 external link
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 external link
Packaging
25 g in poly bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  Link/
  • • Naisbitt DJ et al. J Pharmacol Exp Ther. 2005 Jun
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PATENTS

PATENTS

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