Acenocoumarol

Summary

Acenocoumarol (CHEMBL397420) is an approved small-molecule anticoagulant (ATC B01AA07) targeting VKORC1; indicated across 4 conditions including thrombotic disease and atrial fibrillation.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AA07
• Targets: 1 (VKORC1)
• Indications: 4 conditions
• Clinical trials: 14
• Chemistry: 353.3 Da · C19H15NO6

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL397420
Name	Acenocoumarol
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	54676537
ChEBI	CHEBI:53766
ATC	B01AA07
Molecular formula	C19H15NO6
Molecular weight	353.3
InChIKey	VABCILAOYCMVPS-UHFFFAOYSA-N

SMILES: CC(=O)CC(C1=CC=C(C=C1)[N+](=O)[O-])C2=C(C3=CC=CC=C3OC2=O)O

IUPAC name: 4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one

ChEBI definition: A hydroxycoumarin that is warfarin in which the hydrogen at position 4 of the phenyl substituent is replaced by a nitro group.

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

Also known as: Acenocoumarol, Acenocumarol, Mini-sintrom, NSC-760052, Sinthrome, acenocoumarol, SID17385821, Acenocoumarin, SID50086853, ACENOCOUMAROL, SID144203981, SID170465636

Patent coverage: 1,690 distinct patent families (6,910 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 6,885 (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	6.11	0%	Q9BQB6

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Glucocorticoid receptor, Alpha-1A adrenergic receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, Nuclear receptor subfamily 1 group I member 2, Prostaglandin G/H synthase 1.

Bioactivity

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

Target	pChembl	Type	Value	Unit	Activity ID
Q63921	5.64	AC50	2300	nM	CHEMBL_ACT_25174658
NR1I2	5.1	AC50	8000	nM	CHEMBL_ACT_25188365
ADRA1A	5	AC50	10000	nM	CHEMBL_ACT_25218263

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
atrial fibrillation	3	MONDO:0004981	EFO:0000275
pulmonary embolism	3	MONDO:0005279	EFO:0003827
melanoma	1	MONDO:0005105	EFO:0000756

Clinical trials

Total trials: 14.

Phase distribution

Phase	Trials
PHASE4	5
Not specified	5
PHASE3	2
PHASE2/PHASE3	1
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00689520	PHASE4	COMPLETED	Long-Term Low-Molecular-Weight Heparin Versus Oral Anticoagulants in Deep Venous Thrombosis
NCT00711308	PHASE4	COMPLETED	Tinzaparin in the Treatment of the Acute Pulmonary Embolism
NCT00966290	PHASE4	COMPLETED	Anticoagulant Clinics and Vitamin K Antagonists
NCT01141153	PHASE4	UNKNOWN	Anticoagulation in Stent Intervention
NCT02826200	PHASE4	UNKNOWN	Rule Out Transcatheter Aortic Valve Thrombosis With Post Implantation Computed Tomography (RETORIC)
NCT02926170	PHASE3	COMPLETED	Rivaroxaban for Patients With Antiphospholipid Syndrome
NCT03153150	PHASE3	COMPLETED	Start or STop Anticoagulants Randomised Trial (SoSTART)
NCT05515120	PHASE2/PHASE3	COMPLETED	Rivaroxaban Plus Aspirin to Manage Recurrent Venous Thromboembolic Events
NCT01851824	PHASE1	COMPLETED	A Study of the Effect of Vemurafenib on the Pharmacokinetics of Acenocoumarol in Patients With BRAFV600 Mutation-Positive Metastatic Malignancy
NCT00512928	Not specified	COMPLETED	Safety Study of Vitamin K2 During Anticoagulation in Human Volunteers
NCT02286414	Not specified	COMPLETED	Benefit/Risk in Real Life of New Oral Anticoagulants and Vitamin K Antagonists in Patients Aged 80 Years and Over
NCT02742480	Not specified	UNKNOWN	Dabigatran Study in the Early Phase of Stroke. New Neuroimaging Markers and Biomarkers Study (SEDMAN STUDY)
NCT03015025	Not specified	COMPLETED	Pharmacogenetic Dosage Algorithm for Acenocoumarol
NCT03154489	Not specified	COMPLETED	Effectiveness of a Multidisciplinary Medication Review With Follow-up for Patients Treated With Coumarin Anticoagulants in Primary Care

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