Masoprocol

Summary

Masoprocol (CHEMBL313972) is an approved small-molecule antineoplastic agent (ATC L01XX10); indicated across 2 conditions including neoplasm.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: L01XX10
• Indications: 2 conditions
• Clinical trials: 1
• Chemistry: 302.4 Da · C18H22O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL313972
Name	Masoprocol
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	71398
ChEBI	CHEBI:73468
ATC	L01XX10
Molecular formula	C18H22O4
Molecular weight	302.4
InChIKey	HCZKYJDFEPMADG-TXEJJXNPSA-N

SMILES: C[C@H](CC1=CC(=C(C=C1)O)O)[C@@H](C)CC2=CC(=C(C=C2)O)O

IUPAC name: 4-[(2S,3R)-4-(3,4-dihydroxyphenyl)-2,3-dimethylbutyl]benzene-1,2-diol

ChEBI definition: The meso-form of nordihydroguaiaretic acid. An antioxidant found in the creosote bush, Larrea divaricata, it is a potent lipoxygenase inhibitor that interferes with arachidonic acid metabolism. It also inhibits (though to a lesser extent) formyltetrahydrofolate synthetase, carboxylesterase, and cyclooxygenase.

Pharmacological roles (ChEBI): antineoplastic agent, lipoxygenase inhibitor, hypoglycemic agent.

Other ChEBI roles (chemical / environmental): metabolite.

Also known as: Actinex, CHX-100, Dihydronorguaiaretic acid, Dinorguaiaretic acid, dihydro-, Insm-18, Insm18, Masoprocol, MESO-NDGA, Meso-nordihydroguaiaretic acid, Nordihydroguaiaretate, Nordihydroguaiaretic acid

Patent coverage: 9,656 distinct patent families (34,716 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 33,257 (96%) 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
	VRAC

Broader ChEMBL bioactivity targets: 56 (assay-derived). Sample: Lysine-specific demethylase 4E, Ubiquitin carboxyl-terminal hydrolase 2, Fructose-bisphosphate aldolase, Prelamin-A/C, ATP-dependent DNA helicase Q1, RecQ-like DNA helicase BLM, Inositol monophosphatase 1, Ferritin light chain, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Thrombopoietin.

Bioactivity

ChEMBL activities: 45 potent at pChembl ≥ 5 of 89 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P08482	7.55	Potency	28.2	nM	CHEMBL_ACT_4803529
CYP3A4	7	Potency	100	nM	CHEMBL_ACT_4949236
CYP3A4	7	Potency	100	nM	CHEMBL_ACT_5078585
HSD17B10	6.9	Potency	125.9	nM	CHEMBL_ACT_4833749
ALDH1A1	6.8	Potency	158.5	nM	CHEMBL_ACT_4177347
PPARG	6.4	AC50	400	nM	CHEMBL_ACT_25113965
PPARG	6.4	AC50	400	nM	CHEMBL_ACT_25114058
ALOX15	6.2	Potency	631	nM	CHEMBL_ACT_4467488
ESR1	6.13	AC50	749	nM	CHEMBL_ACT_25167384
POLB	6.1	Potency	794.3	nM	CHEMBL_ACT_5075345
PGR	6.03	AC50	945	nM	CHEMBL_ACT_25222197
HSD17B10	6	Potency	1000	nM	CHEMBL_ACT_4877198
ALOX15	5.9	Potency	1259	nM	CHEMBL_ACT_4009003
CYP2C9	5.8	Potency	1585	nM	CHEMBL_ACT_5037631
DRD3	5.75	AC50	1800	nM	CHEMBL_ACT_25193611
HSD17B10	5.6	Potency	2512	nM	CHEMBL_ACT_3691687
RECQL	5.6	Potency	2512	nM	CHEMBL_ACT_3694421
PDE4D	5.55	AC50	2800	nM	CHEMBL_ACT_25185413
ALOX12	5.55	Potency	2818	nM	CHEMBL_ACT_4527202
PTGS2	5.51	AC50	3100	nM	CHEMBL_ACT_25166271
PDE4D	5.51	AC50	3100	nM	CHEMBL_ACT_25185941
HPGD	5.5	Potency	3162	nM	CHEMBL_ACT_4804744
SLC6A3	5.47	AC50	3400	nM	CHEMBL_ACT_25124034
ADORA3	5.39	AC50	4100	nM	CHEMBL_ACT_25134809
PDE4D	5.38	AC50	4200	nM	CHEMBL_ACT_25185412
ADORA3	5.33	AC50	4700	nM	CHEMBL_ACT_25134294
THPO	5.3	Potency	5012	nM	CHEMBL_ACT_4809382
THPO	5.3	Potency	5012	nM	CHEMBL_ACT_5070393
SLC6A3	5.28	AC50	5200	nM	CHEMBL_ACT_25124551
SLC6A3	5.27	AC50	5400	nM	CHEMBL_ACT_25124035

Target pathways

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

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
neoplasm	4	MONDO:0005070	EFO:0000616

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

Clinical trials

Total trials: 1.

Phase distribution

Phase	Trials
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00313534	PHASE1	TERMINATED	Nordihydroguaiaretic Acid in Treating Patients With Nonmetastatic Relapsed Prostate Cancer

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).