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Showing drug card for Phenindione (DB00498)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:50
Primary Accession Number DB00498
Secondary Accession Number
  • APRD00166
Name Phenindione
Drug Type
  • Approved
  • Small Molecule
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)
Synonyms Not Available
Brand Names
  1. Athrombon
  2. Bindan
  3. Cronodione
  4. Danedion
  5. Danilon
  6. Danilone
  7. Diadilan
  8. Dindevan
  9. Dineval
  10. Diophindane
  11. Emandion
  12. Emandione
  13. Eridione
  14. Fenhydren
  15. Fenilin
  16. Fenindion
  17. Hedulin
  18. Hemolidione
  19. Indema
  20. Indion
  21. Indon
  22. PID
  23. Phenhydren
  24. Phenillin
  25. Phenylen
  26. Phenylin
  27. Phenylindanedione
  28. Phenylindione
  29. Phenyline
  30. Phenyllin
  31. Pindione
  32. Rectadione
  33. Theradione
  34. Thrombasal
  35. Tromazal
  36. Trombol
Brand Mixtures Not Available
Chemical IUPAC Name 2-phenylindene-1,3-dione
Chemical Formula C15H10O2
Chemical Structure Structure
CAS Registry Number 83-12-5
InChI Identifier InChI=1/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-UHFFFAOYAZ
KEGG Drug Not Available
KEGG Compound C07584 Link Image
PubChem Compound 4760 Link Image
PubChem Substance 9786 Link Image
ChEBI ID 8066 Link Image
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Phenindione Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 222.2387
Monoisotopic Molecular Weight 222.0681
State Solid
Melting Point 148-151 oC
Experimental Water Solubility 27 mg/L (at 20 oC) Source: PhysProp
Predicted Water Solubility 2.30e-02 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 2.6 Source: PhysProp
Predicted LogP 3.10 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.98 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1
Canonical SMILES O=C1C(C(=O)C2=CC=CC=C12)C1=CC=CC=C1
Drug Category
  • Anticoagulants
ATC Codes
AHFS Codes Not Available
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.
Mechanism of Action 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.
Absorption Absorbed slowly from the gastrointestinal tract.
Toxicity Oral, mouse: LD50 = 175 mg/kg; Oral, rat: LD50 = 163 mg/kg.
Protein Binding 88%
Biotransformation Hepatic.
Half Life 5-10 hours
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. [PubMed Link Image]
  2. Wikipedia Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Vitamin K epoxide reductase complex subunit 1
Drug Target 1 [top]
Target 1 ID 787
Target 1 Name Vitamin K epoxide reductase complex subunit 1
Target 1 Synonyms
  1. EC 1.1.4.1
  2. Vitamin K1 2,3-epoxide reductase subunit 1
Target 1 Gene Name VKORC1
Target 1 Protein Sequence >Vitamin K epoxide reductase complex subunit 1 
MGSTWGSPGWVRLALCLTGLVLSLYALHVKAARARDRDYRALCDVGTAISCSRVFSSRWG
RGFGLVEHVLGQDSILNQSNSIFGCIFYTLQLLLGCLRTRWASVLMLLSSLVSLAGSVYL
AWILFFVLYDFCIVCITTYAINVSLMWLSFRKVQEPQGKAKRH
Target 1 Number of Residues 165
Target 1 Molecular Weight 18235
Target 1 Theoretical pI 9.58
Target 1 GO Classification Not Available
Target 1 General Function Involved in vitamin-K-epoxide reductase (warfarin-sensitive) activity
Target 1 Specific Function Involved in vitamin K metabolism. Catalytic subunit of the vitamin K epoxide reductase (VKOR) complex which reduces inactive vitamin K 2,3-epoxide to active vitamin K
Target 1 Pathways
Name SMPDB Link KEGG Link
Biosynthesis of steroids map00100 Link Image
Target 1 Reactions
  • 2-methyl-3-phytyl-1,4-naphthoquinone + oxidized dithiothreitol = 2,3-epoxy-2,3-dihydro-2-methyl-3-phytyl-1,4-naphthoquinone + 1,4-dithiothreitol
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 9-29
  • 101-123
  • 127-149
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 40217983 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q9BQB6 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name VKOR1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Endoplasmic reticulum
  • endoplasmic reticulum membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >492 bp 
ATGGGCAGCACCTGGGGGAGCCCTGGCTGGGTGCGGCTCGCTCTTTGCCTGACGGGCTTA
GTGCTCTCGCTCTACGCGCTGCACGTGAAGGCGGCGCGCGCCCGGGACCGGGATTACCGC
GCGCTCTGCGACGTGGGCACCGCCATCAGCTGTTCGCGCGTCTTCTCCTCCAGGTGGGGC
AGGGGTTTCGGGCTGGTGGAGCATGTGCTGGGACAGGACAGCATCCTCAATCAATCCAAC
AGCATATTCGGTTGCATCTTCTACACACTACAGCTATTGTTAGGTTGCCTGCGGACACGC
TGGGCCTCTGTCCTGATGCTGCTGAGCTCCCTGGTGTCTCTCGCTGGTTCTGTCTACCTG
GCCTGGATCCTGTTCTTCGTGCTCTATGATTTCTGCATTGTTTGTATCACCACCTATGCT
ATCAACGTGAGCCTGATGTGGCTCAGTTTCCGGAAGGTCCAAGAACCCCAGGGCAAGGCT
AAGAGGCACTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID VKORC1 Link Image
Target 1 GenAtlas ID VKORC1 Link Image
Target 1 HGNC ID HGNC:23663 Link Image
Target 1 Chromosome Location 16
Target 1 Locus 16p11.2
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Clark HF, Gurney AL, Abaya E, Baker K, Baldwin D, Brush J, Chen J, Chow B, Chui C, Crowley C, Currell B, Deuel B, Dowd P, Eaton D, Foster J, Grimaldi C, Gu Q, Hass PE, Heldens S, Huang A, Kim HS, Klimowski L, Jin Y, Johnson S, Lee J, Lewis L, Liao D, Mark M, Robbie E, Sanchez C, Schoenfeld J, Seshagiri S, Simmons L, Singh J, Smith V, Stinson J, Vagts A, Vandlen R, Watanabe C, Wieand D, Woods K, Xie MH, Yansura D, Yi S, Yu G, Yuan J, Zhang M, Zhang Z, Goddard A, Wood WI, Godowski P, Gray A: The secreted protein discovery initiative (SPDI), a large-scale effort to identify novel human secreted and transmembrane proteins: a bioinformatics assessment. Genome Res. 2003 Oct;13(10):2265-70. Epub 2003 Sep 15. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.