Phenprocoumon

Summary

Phenprocoumon (CHEMBL1465) is an approved small-molecule anticoagulant (ATC B01AA04) targeting VKORC1; indicated across 4 conditions including thrombotic disease and melanoma.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AA04
• Targets: 1 (VKORC1)
• Indications: 4 conditions
• Clinical trials: 15
• Chemistry: 280.3 Da · C18H16O3

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1465
Name	Phenprocoumon
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	54680692
ChEBI	CHEBI:50438
ATC	B01AA04
Molecular formula	C18H16O3
Molecular weight	280.3
InChIKey	DQDAYGNAKTZFIW-UHFFFAOYSA-N

SMILES: CCC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O

IUPAC name: 4-hydroxy-3-(1-phenylpropyl)chromen-2-one

ChEBI definition: A hydroxycoumarin that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenylpropyl group.

Pharmacological roles (ChEBI): anticoagulant, EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor.

Also known as: BS-7565, Fencumar, Fenprocumon, Liquamar, Marcoumar, Marcumar, Phenprocoumarol, Phenprocoumarole, Phenprocoumon, Phenprocoumone, Phenprocumone, PHENPROCOUMON

Patent coverage: 1,690 distinct patent families (7,046 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 7,036 (100%) 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: 1 (assay-derived). Sample: Vitamin K epoxide reductase complex subunit 1.

Bioactivity

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

Target	pChembl	Type	Value	Unit	Activity ID
Q6TEK4	6.7	Ki	200	nM	CHEMBL_ACT_18028575

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

4 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
melanoma	1	MONDO:0005105	EFO:0000756

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

Clinical trials

Total trials: 15.

Phase distribution

Phase	Trials
PHASE4	7
Not specified	3
PHASE3	2
PHASE2	2
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00528671	PHASE4	TERMINATED	Very Low Dose Oral Anticoagulation and Thromboembolic and Bleeding Complications
NCT00586287	PHASE4	COMPLETED	Study to Find Out the Appropriate Initial Dose of the Anticoagulant Drug Phenprocoumon
NCT01339819	PHASE4	COMPLETED	Impact of Dabigatran and Phenprocoumon on ADP Induced Platelet Aggregation in Patients With Atrial Fibrillation
NCT01352702	PHASE4	TERMINATED	Impact of Dabigatran and Phenprocoumon on Clopidogrel Mediated ADP Induced Platelet Aggregation in Patients With Atrial Fibrillation
NCT01812200	PHASE4	COMPLETED	Antithrombotic Triple Therapy in Humans
NCT02591225	PHASE4	UNKNOWN	Left Atrial Thrombus Reduction - Effect of Dabigatran Versus Phenprocoumon
NCT03463317	PHASE4	COMPLETED	Left Atrial Appendage CLOSURE in Patients With Atrial Fibrillation Compared to Medical Therapy
NCT00895505	PHASE3	UNKNOWN	D-Dimer Guided Oral Anticoagulant Treatment (OAT)
NCT02933697	PHASE3	COMPLETED	Compare Apixaban and Vitamin-K Antagonists in Patients With Atrial Fibrillation (AF) and End-Stage Kidney Disease (ESKD)
NCT02256683	PHASE2	TERMINATED	Resolution of Left Atrial-Appendage Thrombus - Effects of Dabigatran in Patients With AF
NCT02872649	PHASE2	TERMINATED	Dabigatran as an Alternative Anticoagulant in Patients With Left Ventricular Assist Device (LVAD)
NCT01849666	PHASE1	COMPLETED	A Study of the Effect of Vemurafenib on the Pharmacokinetics of Phenprocoumon in Patients With BRAFV600 Mutation-Positive Metastatic Malignancy
NCT02090543	Not specified	COMPLETED	BAY 59-7939 (Xarelto, SPAF), Non Interventional Studies
NCT03563937	Not specified	COMPLETED	Real-world Comparative Effectiveness of Stroke Prevention in Patients With Atrial Fibrillation Treated With Factor Xa Non-vitamin-K Oral Anticoagulants (NOACs) vs. Phenprocoumon
NCT04444804	Not specified	COMPLETED	Study to Compare the Effectiveness of Rivaroxaban (Xarelto) Versus Low-molecular-weight Heparin (LMWH) and Phenprocoumon for the Treatment and Secondary Prevention of Venous Thromboembolism in Routine Clinical Practice in Germany

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

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