Phenindione

Summary

Phenindione (CHEMBL711) is an approved small-molecule anticoagulant (ATC B01AA02) targeting VKORC1; indicated across 2 conditions including thrombotic disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AA02
• Targets: 1 (VKORC1)
• Indications: 2 conditions
• Clinical trials: 2
• Chemistry: 222.24 Da · C15H10O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL711
Name	Phenindione
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4760
ChEBI	CHEBI:8066
ATC	B01AA02
Molecular formula	C15H10O2
Molecular weight	222.24
InChIKey	NFBAXHOPROOJAW-UHFFFAOYSA-N

SMILES: C1=CC=C(C=C1)C2C(=O)C3=CC=CC=C3C2=O

IUPAC name: 2-phenylindene-1,3-dione

Pharmacological roles (ChEBI): anticoagulant.

Also known as: Danilone, Dindevan, Fenindiona, Hedulin, NSC-41693, Phenindione, SID11532881, SID26748198, PHENINDIONE, SID11112218, SID26748199, SID50107356

Patent coverage: 1,981 distinct patent families (6,950 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 6,892 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
VKORC1	vitamin K epoxide reductase complex subunit 1	Inhibition		0%	Q9BQB6

Broader ChEMBL bioactivity targets: 9 (assay-derived). Sample: Microtubule-associated protein tau, Prelamin-A/C, Ferritin light chain, 5-hydroxytryptamine receptor 2B, Polyunsaturated fatty acid 5-lipoxygenase, Cytochrome P450 1A2, Cytochrome P450 3A4, Mitogen-activated protein kinase 1, Cellular tumor antigen p53.

Bioactivity

ChEMBL activities: 3 potent at pChembl ≥ 5 of 10 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
LMNA	5.45	Potency	3548	nM	CHEMBL_ACT_3658093
MAPK1	5.25	Potency	5623	nM	CHEMBL_ACT_4741877
TP53	5	Potency	10000	nM	CHEMBL_ACT_4874682

Target pathways

Aggregated over 1 target gene(s): VKORC1.

Top Reactome pathways

1 total, by targets touching each:

Pathway	Targets	Genes
Metabolism of vitamin K	1	VKORC1

Dominant GO biological processes

GO term	Targets
xenobiotic metabolic process	1
blood coagulation	1
peptidyl-glutamic acid carboxylation	1
vitamin K metabolic process	1
positive regulation of coagulation	1
bone development	1

Indications & clinical

Indications

2 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
thrombotic disease	4	MONDO:0000831	HP:0004419

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 2.

Phase distribution

Phase	Trials
PHASE3	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01758640	PHASE3	COMPLETED	Safety And Efficacy of Low Dose Oral Anticoagulants And Aspirin Therapy
NCT03153150	PHASE3	COMPLETED	Start or STop Anticoagulants Randomised Trial (SoSTART)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

2 molecules share ≥1 primary target. Top 2 by shared-target count:

Molecule	Source	Status	Shared targets
WARFARIN	ChEMBL + PubChem	Phase 4 (approved)	VKORC1
alitretinoin	PubChem	Approved	VKORC1