Phenindione

Chemical compound

AU: D
Passes into breast milk

Routes of
administrationOralATC code

B01AA02 (WHO)

Pharmacokinetic dataProtein binding88%Elimination half-life5 to 10 hoursIdentifiers

IUPAC name

2-phenyl-1H-indene-1,3(2H)-dione

CAS Number

83-12-5^Y

PubChem CID

4760

IUPHAR/BPS

6838

DrugBank

DB00498^Y

ChemSpider

4596^Y

UNII

5M7Y6274ZE

KEGG

D08354^Y

ChEBI

CHEBI:8066^Y

ChEMBL

ChEMBL711^Y

CompTox Dashboard (EPA)

DTXSID5023453

ECHA InfoCard100.001.323

Chemical and physical dataFormulaC₁₅H₁₀O₂Molar mass222.243 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

O=C2c1ccccc1C(=O)C2c3ccccc3

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^Y
Key:NFBAXHOPROOJAW-UHFFFAOYSA-N^Y

(verify)

Phenindione is an anticoagulant which functions as a Vitamin K antagonist.

Phenindione was introduced in the early 1950s. It acts similar to warfarin, but it has been associated with hypersensitivity reactions, so it is rarely used and warfarin is preferred.^[1]^[2]

References

^ Naisbitt DJ, Farrell J, Chamberlain PJ, Hopkins JE, Berry NG, Pirmohamed M, Park BK (June 2005). "Characterization of the T-cell response in a patient with phenindione hypersensitivity". The Journal of Pharmacology and Experimental Therapeutics. 313 (3): 1058–65. doi:10.1124/jpet.105.083758. PMID 15743920. S2CID 17052792.
^ Sweetman SC, ed. (2009). Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. "Phenindione", p. 1369.

External links

Diseases Database (DDB): 30536

Antithrombotics (thrombolytics, anticoagulants and antiplatelet drugs) (B01)

Antiplatelet drugs

Glycoprotein IIb/IIIa inhibitors	Abciximab Eptifibatide Orbofiban Roxifiban Sibrafiban^§ Tirofiban
ADP receptor/P2Y₁₂ inhibitors	Thienopyridines Clopidogrel Prasugrel Ticlopidine Nucleotide/nucleoside analogs Cangrelor Elinogrel Ticagrelor
Prostaglandin analogue (PGI2)	Beraprost Iloprost Prostacyclin Treprostinil
COX inhibitors	Acetylsalicylic acid/Aspirin^# Aloxiprin Carbasalate calcium Indobufen Triflusal
Thromboxane inhibitors	Thromboxane synthase inhibitors Dipyridamole (+ aspirin) Picotamide Terbogrel Receptor antagonists Terbogrel Terutroban^§
Phosphodiesterase inhibitors	Cilostazol Dipyridamole Triflusal
Other	Cloricromen Ditazole Vorapaxar

Anticoagulants

Vitamin K antagonists
(inhibit II, VII, IX, X)

Factor Xa inhibitors
(with some II inhibition)

Heparin group/ glycosaminoglycans/ (bind antithrombin)	Low-molecular-weight heparin Bemiparin Certoparin Dalteparin Enoxaparin Nadroparin Parnaparin Reviparin Tinzaparin Oligosaccharides Fondaparinux Idraparinux^§ Heparinoids Danaparoid Dermatan sulfate Sulodexide
Direct Xa inhibitors ("xabans")	Apixaban Betrixaban Darexaban^§ Edoxaban Otamixaban^§ Rivaroxaban