Menadione

Summary

Menadione (CHEMBL590) is an approved small-molecule angiogenesis inhibitor (ATC B02BA02); indicated across 1 condition.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: B02BA02
• Indications: 1 condition
• Clinical trials: 3
• Chemistry: 172.18 Da · C11H8O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL590
Name	Menadione
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	4055
ChEBI	CHEBI:28869
ATC	B02BA02
Molecular formula	C11H8O2
Molecular weight	172.18
InChIKey	MJVAVZPDRWSRRC-UHFFFAOYSA-N

SMILES: CC1=CC(=O)C2=CC=CC=C2C1=O

IUPAC name: 2-methylnaphthalene-1,4-dione

ChEBI definition: A member of the class of 1,4-naphthoquinones that is 1,4-naphthoquinone which is substituted at position 2 by a methyl group. It is used as a nutritional supplement and for the treatment of hypoprothrombinemia.

Pharmacological roles (ChEBI): nutraceutical, angiogenesis inhibitor, EC 3.4.22.69 (SARS coronavirus main proteinase) inhibitor, antineoplastic agent.

Other ChEBI roles (chemical / environmental): human urinary metabolite.

Also known as: Kayquinone, Menadione, NSC-4170, Vitamin k 3, Vitamin k3, menadione, mendione, Vitamin-K3, Menadion, SID11112142, SID11532917, SID26748651

Patent coverage: 8,663 distinct patent families (21,034 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 18,599 (88%) 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

Broader ChEMBL bioactivity targets: 51 (assay-derived). Sample: Pyruvate kinase PKM, Microtubule-associated protein tau, Ubiquitin carboxyl-terminal hydrolase 2, Nuclear receptor ROR-gamma, Survival motor neuron protein, Fructose-bisphosphate aldolase, Prelamin-A/C, RecQ-like DNA helicase BLM, Inositol monophosphatase 1, 4’-phosphopantetheinyl transferase ffp.

Bioactivity

ChEMBL activities: 44 potent at pChembl ≥ 5 of 91 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
Q5FB27	6.96	IC50	110	nM	CHEMBL_ACT_5102837
O54754	6.82	IC50	150	nM	CHEMBL_ACT_5102813
CYP1A2	6.8	AC50	158.5	nM	CHEMBL_ACT_6007653
Q9Z0U5	6.72	IC50	190	nM	CHEMBL_ACT_5102819
AOX1	6.7	IC50	200	nM	CHEMBL_ACT_5102807
IDO1	6.43	IC50	370	nM	CHEMBL_ACT_18276599
MAOB	6.4	Ki	400	nM	CHEMBL_ACT_7969089
AOX1	6.33	Ki	470	nM	CHEMBL_ACT_15459134
A8B2U2	6.25	Potency	561	nM	CHEMBL_ACT_4588510
A8B2U2	6.25	Potency	561	nM	CHEMBL_ACT_4605842
TST	6	IC50	1000	nM	CHEMBL_ACT_19209172
IDO1	6	IC50	1000	nM	CHEMBL_ACT_2120202
IDO1	5.96	IC50	1100	nM	CHEMBL_ACT_3459552
AOX1	5.82	Ki	1500	nM	CHEMBL_ACT_15459127
SMN1	5.8	Potency	1585	nM	CHEMBL_ACT_3888786
P80456	5.7	IC50	2000	nM	CHEMBL_ACT_5102834
CDC25B	5.66	IC50	2200	nM	CHEMBL_ACT_12200432
CYP2C19	5.6	Potency	2512	nM	CHEMBL_ACT_4020451
MAPK1	5.6	Potency	2512	nM	CHEMBL_ACT_4545106
CYP2C19	5.6	AC50	2512	nM	CHEMBL_ACT_6069275
P97697	5.55	Potency	2818	nM	CHEMBL_ACT_4415811
CDC25B	5.47	IC50	3380	nM	CHEMBL_ACT_2407263
P0DTD1	5.43	IC50	3670	nM	CHEMBL_ACT_26165127
CDC25B	5.41	IC50	3900	nM	CHEMBL_ACT_18890607
MAPT	5.3	Potency	5012	nM	CHEMBL_ACT_4012822
P00811	5.25	Potency	5623	nM	CHEMBL_ACT_4695308
P51450	5.2	Potency	6310	nM	CHEMBL_ACT_4091306
P97697	5.2	Potency	6310	nM	CHEMBL_ACT_4409300
P00883	5.2	Potency	6310	nM	CHEMBL_ACT_4588188
USP2	5.2	Potency	6310	nM	CHEMBL_ACT_4731828

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 indication (1 at ChEMBL trial phase 4).

The 1 indication record carries no mapped disease name (EFO/MeSH-only); none shown.

Clinical trials

Total trials: 3.

Phase distribution

Phase	Trials
PHASE2	1
PHASE1	1
Not specified	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01094444	PHASE2	COMPLETED	Investigation of the Effect of Vitamin K3-lotion for the Treatment of Cetuximab Induced Folliculitis
NCT00656786	PHASE1	COMPLETED	Safety, Tolerability and Systemic Absorption of Menadione Topical Lotion for Epidermal-Growth-Factor-Receptor (EGFR) Inhibitor-Associated Rash
NCT01393821	Not specified	COMPLETED	Menadione Topical Lotion in Treating Skin Discomfort and Psychological Distress in Patients With Cancer Receiving Panitumumab, Erlotinib Hydrochloride, or Cetuximab

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

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).