Compound Detail

CHEMBL279785

MARIMASTAT

🧪 Phase III

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🧪 Phase III

CNC(=O)[C@@H](NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO)C(C)(C)C

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL279785
Name	MARIMASTAT
Phase	Phase III
Structure Type	MOL
InChI Key	OCSMOTCMPXTDND-OUAUKWLOSA-N

Known Names

BB 2516 BB-2516 BB2516 GI 5712 GI-5712 GI5712 KB-R 8898 Marimastat NSC-719333 TA 2516 TA-2516 TA2516

Targets

128

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

331.4

MW (Da)

-0.21

ALogP

HBA

HBD

127.8

PSA (Å²)

0.33

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

USAN Stem	-stat
USAN Year	1996

Extended Properties

Molecular Formula	C15H29N3O5
MW	331.41
Aromatic Rings	0
Heavy Atoms	23
NP-Likeness	0.53

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Matrix metalloproteinase 9 inhibitor	INHIBITOR	Matrix metalloproteinase-9	✓	✓
Matrix metalloproteinase-1 inhibitor	INHIBITOR	Interstitial collagenase	✓	✓
Matrix metalloproteinase 12 inhibitor	INHIBITOR	Macrophage metalloelastase	✓	✓
Matrix metalloproteinase-2 inhibitor	INHIBITOR	72 kDa type IV collagenase	✓	✓
Matrix metalloproteinase 3 inhibitor	INHIBITOR	Stromelysin-1	✓	✓
Matrix metalloproteinase 7 inhibitor	INHIBITOR	Matrilysin	✓	✓

Indications

Breast Neoplasms Lung Neoplasms

Activity Summary

IC50 115 meas. best 9.39

Ki 13 meas. best 9.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Disintegrin and metalloproteinase domain-containing protein 17 CHEMBL3706	Ki	9.4	9.0	0.4	3
72 kDa type IV collagenase CHEMBL333	IC50	9.39	8.5294	0.4	18
Neutrophil collagenase CHEMBL4588	IC50	9.33	8.3786	0.5	7
72 kDa type IV collagenase CHEMBL333	Ki	9.22	9.22	0.6	1
Interstitial collagenase CHEMBL332	Ki	9.15	9.0233	0.7	3
Collagenase 3 CHEMBL280	IC50	9.13	8.5509	0.7	11
Interstitial collagenase CHEMBL332	IC50	9.11	8.4413	0.8	15
Matrix metalloproteinase-9 CHEMBL321	IC50	9.1	8.17	0.8	13
Matrix metalloproteinase-14 CHEMBL3869	IC50	8.74	7.4933	1.8	3
Stromelysin-1 CHEMBL283	Ki	8.62	7.7075	2.4	4
Disintegrin and metalloproteinase domain-containing protein 17 CHEMBL3706	IC50	8.42	6.8457	3.8	7
Matrilysin CHEMBL4073	IC50	8.39	7.5233	4.1	6
Stromelysin-1 CHEMBL283	IC50	8.36	7.5036	4.4	11
Matrix metalloproteinase-9 CHEMBL321	Ki	7.96	7.96	11.0	2
Unchecked CHEMBL612545	IC50	7.45	7.335	35.8	2
Stromelysin-2 CHEMBL4270	IC50	7.16	6.08	69.0	2
Tumor necrosis factor CHEMBL1825	IC50	6.0	6.0	1001.0	1
ADMET CHEMBL612558	IC50	6.0	5.4	1000.0	5
THP-1 CHEMBL614245	IC50	5.68	5.68	2100.0	1
Matrix metalloproteinase-15 CHEMBL2963	IC50	5.0	5.0	10000.0	1
A disintegrin and metalloproteinase with thrombospondin motifs 4 CHEMBL2318	IC50	5.0	5.0	10000.0	1
A disintegrin and metalloproteinase with thrombospondin motifs 5 CHEMBL2285	IC50	5.0	5.0	10000.0	1
Macrophage metalloelastase CHEMBL4393	IC50	5.0	5.0	10000.0	1
Matrix metalloproteinase-16 CHEMBL2200	IC50	5.0	5.0	10000.0	1
Matrix metalloproteinase-26 CHEMBL4707	IC50	5.0	5.0	10000.0	1
Matrix metalloproteinase-24 CHEMBL5050	IC50	5.0	5.0	10000.0	1
Matrix metalloproteinase-20 CHEMBL1938226	IC50	5.0	5.0	10000.0	1
Matrix metalloproteinase-25 CHEMBL1795103	IC50	5.0	5.0	10000.0	1
Zinc metalloproteinase dpy-31 CHEMBL3739251	IC50	4.1	4.1	79432.8	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	582.4	ng.hr.mL-1	Rattus norvegicus
AUC	582.4	ng.hr.mL-1	Rattus norvegicus
Cmax	419.42	nM	Rattus norvegicus
Cmax	419.42	nM	Rattus norvegicus
Cmax	7241.79	nM	Rattus norvegicus
F	15.0	%	Primates
T1/2	27.0	hr	Primates
T1/2	0.9	hr	Rattus norvegicus
T1/2	0.9	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Disintegrin and metalloproteinase domain-containing protein 17	Ki	=	0.4	nM	9.4	Inhibition of recombinant human TNF-alpha converting enzyme (TACE)	12873504
Disintegrin and metalloproteinase domain-containing protein 17	Ki	=	0.4	nM	9.4	Inhibition of recombinant human tumor necrosis factor-alpha converting enzyme	12873505
72 kDa type IV collagenase	IC50	=	0.41	nM	9.39	Inhibition of MMP-2 (unknown origin)	34157437
72 kDa type IV collagenase	IC50	=	0.41	nM	9.39	In vitro selective inhibition against matrix metalloprotease-2 (MMP-2) using flu...	11754593
72 kDa type IV collagenase	IC50	=	0.43	nM	9.37	Inhibition of MMP2 (unknown origin) preincubated for 1 hr followed by (QF)-24 su...	30537832
72 kDa type IV collagenase	IC50	=	0.43	nM	9.37	Inhibition of MMP2 (unknown origin) using QF-24 as substrate preincubated for 1 ...	31251594
Neutrophil collagenase	IC50	=	0.47	nM	9.33	Inhibition of MMP-8 (unknown origin)	34157437
Neutrophil collagenase	IC50	=	0.47	nM	9.33	Inhibition of Matrix metalloprotease-8 (MMP-8) in fluorimetric assay	11754593
72 kDa type IV collagenase	Ki	=	0.6	nM	9.22	Inhibitory potency against Matrix metalloprotease-2 (MMP-2)	12014967
Interstitial collagenase	Ki	=	0.7	nM	9.15	Inhibitory potency against Matrix metalloprotease-1 (MMP-1)	12014967
Collagenase 3	IC50	=	0.74	nM	9.13	Inhibition of MMP-13 (unknown origin)	35969157
72 kDa type IV collagenase	IC50	=	0.75	nM	9.12	50 percent inhibition of human Matrix metalloprotease-2 by the cleavage of fluor...	11133099
72 kDa type IV collagenase	IC50	=	0.75	nM	9.12	Inhibitory activity against human Matrix metalloprotease-2	11591510
Interstitial collagenase	IC50	=	0.78	nM	9.11	In vitro selective inhibition against matrix metalloprotease-1 (MMP-1) using a f...	11754593
Interstitial collagenase	IC50	=	0.78	nM	9.11	Inhibition of MMP-1 (unknown origin)	34157437
Matrix metalloproteinase-9	IC50	=	0.79	nM	9.1	Inhibition of MMP-9 (unknown origin)	34157437
Matrix metalloproteinase-9	IC50	=	0.79	nM	9.1	In vitro selective inhibition against Matrix metalloprotease-9 (MMP-9) using flu...	11754593
72 kDa type IV collagenase	IC50	=	0.85	nM	9.07	In vitro inhibitory activity against matrix metalloprotease 2 isolated from huma...	9873712
Interstitial collagenase	IC50	=	1.0	nM	9.0	Inhibition of human recombinant MMP-1 incubated for 30 mins by fluorescence base...	37158732
Interstitial collagenase	IC50	=	1.1	nM	8.96	In vitro inhibitory activity against matrix metalloprotease 1 isolated from the ...	9873712

Literature References

PubMed	DOI	Target Context	# Activities
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
9871766	10.1016/s0960-894x(98)00218-2	Rattus norvegicus	5
11378378	10.1016/s0960-894x(01)00259-1	ADMET	5
-	10.6019/CHEMBL4495565	SARS-CoV-2	4
20014752	10.1021/tx900326k	Hepatotoxicity	3
11549451	10.1016/s0960-894x(01)00487-5	Rattus norvegicus	3
9873712	10.1016/s0960-894x(98)00597-6	ADMET	2
-	10.6019/CHEMBL4651402	SARS-CoV-2	2
-	10.6019/CHEMBL4495564	Replicase polyprotein 1ab	2
10579851	10.1021/jm990377j	Disintegrin and metalloproteinase domain-containing protein 17	2
26546217	10.1016/j.bmcl.2015.10.077	Zinc metalloproteinase dpy-31	2
10522712	10.1016/s0960-894x(99)00494-1	Rattus norvegicus	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
26192023	10.1021/acs.jmedchem.5b00354	Disintegrin and metalloproteinase domain-containing protein 17	2
37158732	10.1021/acs.jmedchem.2c02107	Stromelysin-2	1
11212095	10.1016/s0960-894x(00)00646-6	Stromelysin-1	1
11212095	10.1016/s0960-894x(00)00646-6	72 kDa type IV collagenase	1
12930146	10.1021/jm0307638	Interstitial collagenase	1
10397503	10.1016/s0960-894x(99)00259-0	Collagenase 3	1

Data from ChEMBL 36 via Core Engine