ContaminantDB: Phenindione

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:20 UTC

Update Date

2026-03-26 21:06:41 UTC

Accession Number

CHEM002441

Identification

Common Name

Phenindione

Class

Small Molecule

Description

Phenindione is only found in individuals that have used or taken this drug. It is 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). Phenindione inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Anticoagulant
Aromatic Hydrocarbon
Drug
Ester
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Phenyl-1,3(2H)-indenedione	ChEBI
2-Phenyl-1,3-diketohydrindene	ChEBI
2-Phenyl-1,3-indandione	ChEBI
Fenindiona	ChEBI
Phenindionum	ChEBI
PID	ChEBI
Hedulin	Kegg
Merck lipha santé brand OF phenindione	HMDB
2 Phenyl 1,3 indandione	HMDB
Boots brand OF phenindione	HMDB
Goldshield brand OF phenindione	HMDB
Phenylindanedione	HMDB
Phenyline	HMDB
Pindione	HMDB
Dindevan	HMDB
Fenilin	HMDB

Chemical Formula

C₁₅H₁₀O₂

Average Molecular Mass

222.239 g/mol

Monoisotopic Mass

222.068 g/mol

CAS Registry Number

83-12-5

IUPAC Name

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

Traditional Name

indon

SMILES

O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1

InChI Identifier

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

InChI Key

NFBAXHOPROOJAW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as indanediones. Indanediones are compounds containing an indane ring bearing two ketone groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Indanedione
Aryl alkyl ketone
Aryl ketone
1,3-diketone
1,3-dicarbonyl compound
Monocyclic benzene moiety
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

aromatic ketone (CHEBI:8066 )
beta-diketone (CHEBI:8066 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

anticoagulant

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	150°C
Boiling Point	Not Available
Solubility	27 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.023 g/L	ALOGPS
logP	3.1	ALOGPS
logP	2.88	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.88	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	65.23 m³·mol⁻¹	ChemAxon
Polarizability	23.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-8950000000-db616a8e7e559a5a5f6f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-9b298f1072fd790bda04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-3390000000-11fefa0e023507256e68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9460000000-25e9eb850e8f08d73284	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-3ff702d3fba3b4ba61c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-782f754ab0024fcab923	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gi9-5940000000-5905bd66b8f78a2f70a3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-4526ea1529fb7968e1f9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2390000000-dafe0249a10821f9782f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-ee672ba3244610e83f29	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-67222288c14ba81150ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-67222288c14ba81150ce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01c0-0920000000-f427c2360b8ee97f9d00	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00di-4690000000-3b0da30c88d7d0ecf339	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Ingestion (5) ; dermal (5). Absorbed slowly from the gastrointestinal tract.

Mechanism of Toxicity

Phenindione inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots. (1)

Metabolism

Hepatic. Half Life: 5-10 hours

Toxicity Values

Oral, mouse: LD50 = 175 mg/kg; Oral, rat: LD50 = 163 mg/kg.

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Phenindione is an anticoagulant drug derived from coumarin. (3) For the treatment of pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, mural thrombosis, and thrombophili. Also used for anticoagulant prophylaxis.

Minimum Risk Level

Not Available

Health Effects

Phenindione is an anticoagulant and may cause internal bleeding, leading to shock, loss of consciousness, and eventually death. (2)

Symptoms

Phenindione may cause bleeding complications. (2)

Treatment

The primary antidote to phenindione poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses phenindione can affect the body for many months, and the antidote must be administered regularly for a long period of time. (2)

Concentrations

Not Available

External Links

DrugBank ID

DB00498

HMDB ID

HMDB0014641

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID