Marimastat

Summary

Marimastat (CHEMBL279785) is a phase-3 clinical-stage small-molecule antineoplastic agent targeting MMP1, MMP2, and MMP3; indicated across 2 conditions including breast neoplasm and lung neoplasm.

At a glance

• Status: Max clinical phase 3 (not approved)
• Modality: Small molecule
• Targets: 8 (MMP1, MMP2, MMP3…)
• Indications: 2 conditions
• Clinical trials: 5
• Chemistry: 331.41 Da · C15H29N3O5

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL279785
Name	Marimastat
Type	Small molecule
Max phase	3
FDA approved	no
PubChem CID	119031
ChEBI	CHEBI:50662
Molecular formula	C15H29N3O5
Molecular weight	331.41
InChIKey	OCSMOTCMPXTDND-OUAUKWLOSA-N

SMILES: CC(C)C[C@H]([C@@H](C(=O)NO)O)C(=O)N[C@H](C(=O)NC)C(C)(C)C

IUPAC name: (2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N’,3-dihydroxy-2-(2-methylpropyl)butanediamide

ChEBI definition: A secondary carboxamide resulting from the foraml condensation of the carboxy group of (2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the α-amino group of N,3-dimethyl-L-valinamide.

Pharmacological roles (ChEBI): antineoplastic agent, matrix metalloproteinase inhibitor.

Also known as: BB 2516, BB-2516, BB2516, GI 5712, GI-5712, GI5712, KB-R 8898, Marimastat, NSC-719333, TA 2516, TA-2516, TA2516

Patent coverage: 6,822 distinct patent families (29,447 SureChEMBL compound mentions), from 1 matched compound structure(s). 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
MMP1	MMP1	Inhibition	8.3	0%	P03956
MMP2	MMP2	Inhibition	8.22	0.1%	P08253
MMP3	MMP3	Inhibition	6.64	0.1%	P08254
MMP7	MMP7	Inhibition	7.8	0.1%	P09237
MMP8	MMP8	Inhibition	8.89	0.4%	P22894
MMP9	MMP9	Inhibition	8.52	0.1%	P14780
MMP10	MMP10	Inhibition	7.16	0.6%	P09238
MMP13	MMP13	Inhibition	8.7	0%	P45452

Broader ChEMBL bioactivity targets: 21 (assay-derived). Sample: Matrix metalloproteinase-25, Tumor necrosis factor, Matrix metalloproteinase-20, Matrix metalloproteinase-16, A disintegrin and metalloproteinase with thrombospondin motifs 5, A disintegrin and metalloproteinase with thrombospondin motifs 4, Collagenase 3, Stromelysin-1, Matrix metalloproteinase-15, Matrix metalloproteinase-9, Interstitial collagenase, 72 kDa type IV collagenase, Disintegrin and metalloproteinase domain-containing protein 17, Zinc metalloproteinase dpy-31, Matrix metalloproteinase-14, Matrilysin, Stromelysin-2, Macrophage metalloelastase, Neutrophil collagenase, Matrix metalloproteinase-26.

Bioactivity

ChEMBL activities: 116 potent at pChembl ≥ 5 of 117 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ADAM17	9.4	Ki	0.4	nM	CHEMBL_ACT_486006
ADAM17	9.4	Ki	0.4	nM	CHEMBL_ACT_545076
MMP2	9.39	IC50	0.41	nM	CHEMBL_ACT_1164939
MMP2	9.39	IC50	0.41	nM	CHEMBL_ACT_24998192
MMP2	9.37	IC50	0.43	nM	CHEMBL_ACT_19120724
MMP2	9.37	IC50	0.43	nM	CHEMBL_ACT_19272623
MMP8	9.33	IC50	0.47	nM	CHEMBL_ACT_1164942
MMP8	9.33	IC50	0.47	nM	CHEMBL_ACT_24998210
MMP2	9.22	Ki	0.6	nM	CHEMBL_ACT_363106
MMP1	9.15	Ki	0.7	nM	CHEMBL_ACT_363105
MMP13	9.13	IC50	0.74	nM	CHEMBL_ACT_24745175
MMP2	9.12	IC50	0.75	nM	CHEMBL_ACT_296111
MMP2	9.12	IC50	0.75	nM	CHEMBL_ACT_658347
MMP1	9.11	IC50	0.78	nM	CHEMBL_ACT_1164938
MMP1	9.11	IC50	0.78	nM	CHEMBL_ACT_24998187
MMP9	9.1	IC50	0.79	nM	CHEMBL_ACT_1164943
MMP9	9.1	IC50	0.79	nM	CHEMBL_ACT_24998201
MMP2	9.07	IC50	0.85	nM	CHEMBL_ACT_979903
MMP1	9	IC50	1	nM	CHEMBL_ACT_25534590
MMP1	8.96	Ki	1.1	nM	CHEMBL_ACT_486003
MMP1	8.96	Ki	1.1	nM	CHEMBL_ACT_545073
MMP1	8.96	IC50	1.1	nM	CHEMBL_ACT_979902
MMP13	8.92	IC50	1.2	nM	CHEMBL_ACT_1164944
MMP13	8.92	IC50	1.2	nM	CHEMBL_ACT_24998212
MMP8	8.89	IC50	1.3	nM	CHEMBL_ACT_25534608
MMP1	8.82	IC50	1.5	nM	CHEMBL_ACT_194265
MMP1	8.82	IC50	1.5	nM	CHEMBL_ACT_72188
MMP9	8.82	IC50	1.5	nM	CHEMBL_ACT_72191
MMP1	8.82	IC50	1.5	nM	CHEMBL_ACT_75968
MMP9	8.8	IC50	1.6	nM	CHEMBL_ACT_194268
MMP9	8.8	IC50	1.6	nM	CHEMBL_ACT_75971
MMP2	8.74	IC50	1.8	nM	CHEMBL_ACT_194266
MMP14	8.74	IC50	1.8	nM	CHEMBL_ACT_24745192
MMP14	8.74	IC50	1.82	nM	CHEMBL_ACT_556755
MMP2	8.74	IC50	1.8	nM	CHEMBL_ACT_75969
MMP8	8.7	IC50	2	nM	CHEMBL_ACT_1061753
MMP13	8.7	IC50	2	nM	CHEMBL_ACT_1061754
MMP8	8.7	IC50	2	nM	CHEMBL_ACT_1168815
MMP8	8.7	IC50	2	nM	CHEMBL_ACT_24745123
MMP13	8.7	IC50	2	nM	CHEMBL_ACT_25534581
MMP13	8.7	IC50	2	nM	CHEMBL_ACT_296112
MMP1	8.7	IC50	2	nM	CHEMBL_ACT_556756
MMP13	8.7	IC50	2	nM	CHEMBL_ACT_658346
MMP2	8.7	IC50	2	nM	CHEMBL_ACT_72189
MMP3	8.62	Ki	2.4	nM	CHEMBL_ACT_1255561
MMP1	8.54	IC50	2.9	nM	CHEMBL_ACT_296113
MMP1	8.54	IC50	2.9	nM	CHEMBL_ACT_658348
MMP9	8.52	IC50	3	nM	CHEMBL_ACT_24745138
MMP9	8.52	IC50	3	nM	CHEMBL_ACT_25004568
MMP9	8.51	IC50	3.1	nM	CHEMBL_ACT_19120727
MMP9	8.51	IC50	3.1	nM	CHEMBL_ACT_19272619
MMP13	8.47	IC50	3.4	nM	CHEMBL_ACT_194269
MMP13	8.47	IC50	3.4	nM	CHEMBL_ACT_75972
MMP13	8.46	IC50	3.5	nM	CHEMBL_ACT_72192
ADAM17	8.42	IC50	3.8	nM	CHEMBL_ACT_1168813
ADAM17	8.42	IC50	3.8	nM	CHEMBL_ACT_2391973
MMP7	8.39	IC50	4.1	nM	CHEMBL_ACT_1164941
MMP7	8.39	IC50	4.1	nM	CHEMBL_ACT_24998208
MMP3	8.36	IC50	4.4	nM	CHEMBL_ACT_556758
MMP9	8.33	IC50	4.7	nM	CHEMBL_ACT_25534617
MMP1	8.3	IC50	5	nM	CHEMBL_ACT_1061750
MMP1	8.3	IC50	5	nM	CHEMBL_ACT_1168814
MMP1	8.3	IC50	5	nM	CHEMBL_ACT_24745011
MMP1	8.3	IC50	5	nM	CHEMBL_ACT_262589
MMP2	8.29	IC50	5.1	nM	CHEMBL_ACT_556757
MMP2	8.25	IC50	5.6	nM	CHEMBL_ACT_25534599
MMP2	8.22	IC50	6	nM	CHEMBL_ACT_1061751
MMP2	8.22	IC50	6	nM	CHEMBL_ACT_24745042
MMP2	8.22	IC50	6	nM	CHEMBL_ACT_25004586
MMP2	8.22	IC50	6	nM	CHEMBL_ACT_262590
ADAM17	8.2	Ki	6.3	nM	CHEMBL_ACT_363103
MMP2	8.1	IC50	8	nM	CHEMBL_ACT_24786196
MMP9	8.1	IC50	8	nM	CHEMBL_ACT_556759
MMP3	8.05	Ki	8.9	nM	CHEMBL_ACT_363107
MMP3	8	IC50	10	nM	CHEMBL_ACT_979904
MMP9	7.96	Ki	11	nM	CHEMBL_ACT_486005
MMP9	7.96	Ki	11	nM	CHEMBL_ACT_545075
MMP7	7.96	IC50	11	nM	CHEMBL_ACT_979905
ADAM17	7.94	IC50	11.47	nM	CHEMBL_ACT_14210121
MMP3	7.85	IC50	14	nM	CHEMBL_ACT_1164940
MMP3	7.85	IC50	14	nM	CHEMBL_ACT_24998197
MMP7	7.7	IC50	20	nM	CHEMBL_ACT_24745102
MMP7	7.7	IC50	20	nM	CHEMBL_ACT_262592
MMP3	7.6	IC50	25	nM	CHEMBL_ACT_194267
MMP3	7.6	IC50	25	nM	CHEMBL_ACT_72190
MMP3	7.6	IC50	25	nM	CHEMBL_ACT_75970
ADAM17	7.59	IC50	25.41	nM	CHEMBL_ACT_14313741
MMP3	7.58	IC50	26	nM	CHEMBL_ACT_24786194
MMP10	7.16	IC50	69	nM	CHEMBL_ACT_25534626
MMP3	7.08	Ki	84	nM	CHEMBL_ACT_486004
MMP3	7.08	Ki	84	nM	CHEMBL_ACT_545074
MMP13	6.89	IC50	128	nM	CHEMBL_ACT_24786187
MMP3	6.7	IC50	200	nM	CHEMBL_ACT_1061752
MMP3	6.7	IC50	200	nM	CHEMBL_ACT_24745071
MMP3	6.7	IC50	200	nM	CHEMBL_ACT_262591
MMP9	6.1	IC50	795	nM	CHEMBL_ACT_24786190
TNF	6	IC50	1001	nM	CHEMBL_ACT_363104
ADAM17	5.39	IC50	4100	nM	CHEMBL_ACT_1255559
ADAM17	5.16	IC50	7000	nM	CHEMBL_ACT_1168816
MMP1	5	IC50	10000	nM	CHEMBL_ACT_16457895

Target pathways

Aggregated over 8 target gene(s): MMP1, MMP2, MMP3, MMP7, MMP8, MMP9, MMP10, MMP13.

Top Reactome pathways

40 total, by targets touching each:

Pathway	Targets	Genes
Collagen degradation	8	MMP1, MMP10, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
Degradation of the extracellular matrix	8	MMP1, MMP10, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
Extracellular matrix organization	8	MMP1, MMP10, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
Activation of Matrix Metalloproteinases	8	MMP1, MMP10, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
Immune System	5	MMP1, MMP2, MMP3, MMP8, MMP9
Cytokine Signaling in Immune system	4	MMP1, MMP2, MMP3, MMP9
Collagen formation	4	MMP13, MMP3, MMP7, MMP9
Signal Transduction	4	MMP2, MMP3, MMP7, MMP9
Assembly of collagen fibrils and other multimeric structures	4	MMP13, MMP3, MMP7, MMP9
Signaling by Interleukins	4	MMP1, MMP2, MMP3, MMP9
Interleukin-4 and Interleukin-13 signaling	4	MMP1, MMP2, MMP3, MMP9
ESR-mediated signaling	4	MMP2, MMP3, MMP7, MMP9
Signaling by Nuclear Receptors	4	MMP2, MMP3, MMP7, MMP9
Extra-nuclear estrogen signaling	4	MMP2, MMP3, MMP7, MMP9
Developmental Biology	2	MMP2, MMP9
Innate Immune System	2	MMP8, MMP9
EPH-Ephrin signaling	2	MMP2, MMP9
Regulation of Insulin-like Growth Factor (IGF) transport and uptake by Insulin-like Growth Factor Binding Proteins (IGFBPs)	2	MMP1, MMP2
Metabolism of proteins	2	MMP1, MMP2
EPH-ephrin mediated repulsion of cells	2	MMP2, MMP9
Axon guidance	2	MMP2, MMP9
MAPK6/MAPK4 signaling	2	MMP10, MMP2
Neutrophil degranulation	2	MMP8, MMP9
Nervous system development	2	MMP2, MMP9
Hemostasis	1	MMP1
Signaling by SCF-KIT	1	MMP9
Cell surface interactions at the vascular wall	1	MMP1
Basigin interactions	1	MMP1
Generic Transcription Pathway	1	MMP13
EGFR Transactivation by Gastrin	1	MMP3
Signaling by GPCR	1	MMP3
GPCR downstream signalling	1	MMP3
G alpha (q) signalling events	1	MMP3
RNA Polymerase II Transcription	1	MMP13
Gene expression (Transcription)	1	MMP13
Gastrin-CREB signalling pathway via PKC and MAPK	1	MMP3
Transcriptional regulation by RUNX2	1	MMP13
RUNX2 regulates genes involved in cell migration	1	MMP13
Signaling by Receptor Tyrosine Kinases	1	MMP9
Dengue Virus-Host Interactions	1	MMP9

Dominant GO biological processes

GO term	Targets
proteolysis	8
extracellular matrix disassembly	8
extracellular matrix organization	8
collagen catabolic process	8
cellular response to UV-A	4
response to amyloid-beta	4
endodermal cell differentiation	3
cellular response to lipopolysaccharide	3
positive regulation of protein-containing complex assembly	2
response to xenobiotic stimulus	2
cell migration	2
protein catabolic process	2
positive regulation of cell migration	2
cellular response to reactive oxygen species	2
ephrin receptor signaling pathway	2

Indications & clinical

Indications

2 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.

Disease (in trials)	Phase	MONDO	EFO
breast neoplasm	3	MONDO:0021100	MONDO:0007254
lung neoplasm	3	MONDO:0021117	MONDO:0008903

Clinical trials

Total trials: 5.

Phase distribution

Phase	Trials
PHASE3	3
PHASE2	1
PHASE1	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00002911	PHASE3	COMPLETED	Marimastat in Treating Patients With Stage III Non-small Cell Lung Cancer
NCT00003010	PHASE3	COMPLETED	Marimastat or No Further Therapy in Treating Women With Metastatic Breast Cancer That Is Responding or Stable Following Chemotherapy
NCT00003011	PHASE3	COMPLETED	Marimastat Following Chemotherapy in Treating Patients With Small Cell Lung Cancer
NCT07500233	PHASE2	NOT_YET_RECRUITING	Trial of Oral Community SVMP INhibitors for Snakebite
NCT00261391	PHASE1	COMPLETED	Phase I Drug Trial for S/E of Marimastat in Disabling Malformations When no Other Options.

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

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.

42 molecules share ≥1 primary target. Top 42 by shared-target count:

Molecule	Source	Status	Shared targets
CTS-1027	ChEMBL	Phase 2	MMP1, MMP10, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
PRINOMASTAT	ChEMBL	Phase 3	MMP1, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
BATIMASTAT	ChEMBL	Phase 2	MMP1, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
CIPEMASTAT	ChEMBL	Phase 2	MMP1, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
ILOMASTAT	ChEMBL	Phase 2	MMP1, MMP13, MMP2, MMP3, MMP7, MMP8, MMP9
DOXYCYCLINE	ChEMBL	Phase 4 (approved)	MMP13, MMP2, MMP3, MMP7, MMP8
QUERCETIN	ChEMBL	Phase 3	MMP1, MMP13, MMP2, MMP3, MMP9
LUTEOLIN	ChEMBL	Phase 2	MMP13, MMP2, MMP3, MMP7, MMP9
REBIMASTAT	ChEMBL	Phase 2	MMP1, MMP2, MMP3, MMP7, MMP9
SOLIMASTAT	ChEMBL	Phase 2	MMP1, MMP2, MMP3, MMP7, MMP9
TANOMASTAT	ChEMBL	Phase 2	MMP1, MMP13, MMP2, MMP3, MMP9
APRATASTAT	ChEMBL	Phase 2	MMP1, MMP13, MMP3, MMP9
ZOLEDRONIC ACID	ChEMBL	Phase 4 (approved)	MMP2, MMP8, MMP9
CAFFEIC ACID	ChEMBL	Phase 3	MMP1, MMP2, MMP9
EPIGALOCATECHIN GALLATE	ChEMBL	Phase 3	MMP1, MMP2, MMP7
CHLORHEXIDINE	ChEMBL	Phase 4 (approved)	MMP2, MMP9
CHLOROXINE	ChEMBL	Phase 4 (approved)	MMP13, MMP9
PRAZOSIN	ChEMBL	Phase 4 (approved)	MMP1, MMP9
TILUDRONIC ACID	ChEMBL	Phase 4 (approved)	MMP2, MMP8
CURCUMIN	ChEMBL	Phase 3	MMP13, MMP9
AMINOQUINURIDE	ChEMBL	Phase 2	MMP1, MMP9
TOSEDOSTAT	ChEMBL	Phase 2	MMP2, MMP9
BUDESONIDE	ChEMBL	Phase 4 (approved)	MMP9
BUSULFAN	ChEMBL	Phase 4 (approved)	MMP9
DACARBAZINE	ChEMBL	Phase 4 (approved)	MMP9
DAUNORUBICIN	ChEMBL	Phase 4 (approved)	MMP2
DOXAZOSIN	ChEMBL	Phase 4 (approved)	MMP1
DOXORUBICIN	ChEMBL	Phase 4 (approved)	MMP2
ECONAZOLE	ChEMBL	Phase 4 (approved)	MMP9
IRINOTECAN	ChEMBL	Phase 4 (approved)	MMP1
NIMESULIDE	ChEMBL	Phase 4 (approved)	MMP1
PYRITHIONE	ChEMBL	Phase 4 (approved)	MMP3
SECOBARBITAL	ChEMBL	Phase 4 (approved)	MMP9
SULFASALAZINE	ChEMBL	Phase 4 (approved)	MMP1
TILUDRONATE DISODIUM	ChEMBL	Phase 4 (approved)	MMP1
ACLARUBICIN	ChEMBL	Phase 3	MMP2
MEDRONIC ACID	ChEMBL	Phase 3	MMP2
(+)-SECOISOLARICIRESINOL	ChEMBL	Phase 2	MMP1
ALDUMASTAT	ChEMBL	Phase 2	MMP2
UBENIMEX	ChEMBL	Phase 2	MMP2
Bortezomib	PubChem	Approved	MMP7
Gallic Acid	PubChem	Approved	MMP7