Dicumarol

Summary

Dicumarol (CHEMBL1466) is an approved small-molecule vitamin K antagonist (ATC B01AA01) targeting VKORC1; indicated across 1 condition including thrombotic disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B01AA01
• Targets: 1 (VKORC1)
• Indications: 1 condition
• Chemistry: 336.3 Da · C19H12O6

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1466
Name	Dicumarol
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	54676038
ChEBI	CHEBI:4513
ATC	B01AA01
Molecular formula	C19H12O6
Molecular weight	336.3
InChIKey	DOBMPNYZJYQDGZ-UHFFFAOYSA-N

SMILES: C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O

IUPAC name: 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one

ChEBI definition: A hydroxycoumarin that is methane in which two hydrogens have each been substituted by a 4-hydroxycoumarin-3-yl group. Related to warfarin, it has been used as an anticoagulant.

Pharmacological roles (ChEBI): vitamin K antagonist, anticoagulant, EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor, Hsp90 inhibitor.

Also known as: Bishydroxycoumarin, Dicoumarol, Dicoumarolum, Dicumarol, NSC-17860, NSC-221570, NSC-41834, dicoumarol, SID11112184, DICUMAROL, Dicoumarin, DICOUMAROL

Patent coverage: 3,186 distinct patent families (12,198 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 12,173 (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: 19 (assay-derived). Sample: Prelamin-A/C, G-protein coupled receptor 35, Thyrotropin receptor, Menin/Histone-lysine N-methyltransferase MLL, Proprotein convertase subtilisin/kexin type 7, Aldo-keto reductase family 1 member B1, 3’,5’-cyclic-AMP phosphodiesterase 4D, NAD(P)H dehydrogenase [quinone] 1, Cytochrome P450 1A2, Cytochrome P450 2C9.

Bioactivity

ChEMBL activities: 28 potent at pChembl ≥ 5 of 37 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P05982	9	Ki	1	nM	CHEMBL_ACT_18397669
NQO1	8.59	IC50	2.6	nM	CHEMBL_ACT_2939794
NQO1	8.3	IC50	5	nM	CHEMBL_ACT_2007002
CYP2C9	7.6	Potency	25.1	nM	CHEMBL_ACT_5025341
CYP2C9	7.6	AC50	25.12	nM	CHEMBL_ACT_6045834
GPR35	7.41	Ki	39	nM	CHEMBL_ACT_13445743
LMNA	7.3	Potency	50.1	nM	CHEMBL_ACT_3642919
CYP2C9	6.52	IC50	300	nM	CHEMBL_ACT_7685532
NQO1	6.46	IC50	350	nM	CHEMBL_ACT_18759418
NQO1	6.39	IC50	404	nM	CHEMBL_ACT_2939823
NQO1	6.35	IC50	450	nM	CHEMBL_ACT_1813344
NQO1	6.35	IC50	450	nM	CHEMBL_ACT_2007003
CYP2C9	6.22	Ki	600	nM	CHEMBL_ACT_1120356
GPR35	5.89	EC50	1300	nM	CHEMBL_ACT_13445755
GPR35	5.89	EC50	1300	nM	CHEMBL_ACT_18198029
PCSK7	5.89	IC50	1300	nM	CHEMBL_ACT_6310619
CYP2C9	5.72	Ki	1900	nM	CHEMBL_ACT_367656
P07943	5.39	IC50	4093	nM	CHEMBL_ACT_7685486
MAPK1	5.35	IC50	4426	nM	CHEMBL_ACT_7687666
CYP3A4	5.3	Potency	5012	nM	CHEMBL_ACT_4973817
CYP3A4	5.3	Potency	5012	nM	CHEMBL_ACT_5042843
CYP3A4	5.3	AC50	5012	nM	CHEMBL_ACT_6057523
PDE4D	5.2	AC50	6300	nM	CHEMBL_ACT_25185017
ALDH1A1	5.2	Potency	6310	nM	CHEMBL_ACT_4165286
GPR35	5.01	EC50	9780	nM	CHEMBL_ACT_13442912
CYP2C19	5	Potency	10000	nM	CHEMBL_ACT_4019454
TP53	5	Potency	10000	nM	CHEMBL_ACT_4850806
CYP2C19	5	AC50	10000	nM	CHEMBL_ACT_6056658

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

1 indication (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

Clinical trials

Total trials: 0.

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