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Merck

M2699

Marimastat

≥98% (HPLC), solid, MMP inhibitor

Synonym(s):

BB2516, (2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl] propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide

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About This Item

Empirical Formula (Hill Notation):
C15H29N3O5
CAS Number:
154039-60-8
Molecular Weight:
331.41
UNSPSC Code:
12352200
PubChem Substance ID:
329817950
NACRES:
NA.77
MDL number:
MFCD00866242
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100

Key Documents

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Product Name

Marimastat, ≥98% (HPLC)

SMILES string

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

InChI key

OCSMOTCMPXTDND-OUAUKWLOSA-N

InChI

1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1

assay

≥98% (HPLC)

form

solid

solubility

DMSO: ≥20 mg/mL

shipped in

wet ice

storage temp.

−20°C

Quality Level

100

Gene Information

—

Related Categories

Application

Marimastat has been used as an inhibitor of:
  • metalloproteinase 2/9 (MMP2/9), to study its effects on exercise-mediated interleukin-6 (IL-6) release in mice
  • metalloproteinase, to determine protease activity in Pseudomonas aeruginosa cultures
  • metalloproteinase 10 (MMP10), to study its effect on monoclonal antibody H3 binding to MMP10

Biochem/physiol Actions

Marimastat is a broad spectrum matrix metalloprotease (MMP) inhibitor

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

M2699-IP: + M2699-5MG: + M2699-BULK: + M2699-VAR: + M2699-25MG:

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Certificates of Analysis (COA)

Lot/Batch Number
0000505251
0000505249
0000505249
0000505251
0000394101

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Amir S Razai et al.
The Journal of biological chemistry, 295(8), 2464-2472 (2020-01-19)
Since their discovery, the matrix metalloproteinase (MMP) family proteases have been considered as therapeutic targets in numerous diseases and disorders. Unfortunately, clinical trials with MMP inhibitors have failed to yield any clinical benefits of these inhibitors. These failures were largely
Stefanie K Menzies et al.
Toxicon: X, 14, 100118-100118 (2022-03-25)
Snakebite envenoming affects more than 250,000 people annually in sub-Saharan Africa. Envenoming by Dispholidus typus (boomslang) results in venom-induced consumption coagulopathy (VICC), whereby highly abundant prothrombin-activating snake venom metalloproteinases (SVMPs) consume clotting factors and deplete fibrinogen. The only available treatment
Timothy W Failes et al.
Journal of inorganic biochemistry, 101(3), 396-403 (2007-01-02)
Fe(III)-salen (N,N-bis(salicylidene)-ethane-1,2-diimine) complexes of simple hydroxamic acids and the MMP (matrix metalloproteinase) inhibitor marimastat have been evaluated as hypoxia activated drug carriers. The aceto- (aha), propion- (pha), benzohydroxamato (bha), and marimastat complexes were prepared and characterised by single crystal X-ray
Brian P Pollack et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 17(13), 4400-4413 (2011-05-19)
Diverse immune-related effects occur with the use of epidermal growth factor receptor inhibitors (EGFRI). In addition to the cutaneous inflammation induced by EGFRIs, these agents have been associated with the exacerbation of autoimmune skin disease and contact hypersensitivity, antiviral effects
M Ohshima et al.
Journal of dental research, 89(11), 1315-1321 (2010-08-27)
The underlying mechanism and the therapeutic regimen for the transition of reversible gingivitis to irreversible periodontitis are unclear. Since transforming growth factor (TGF)-β has been implicated in differentially regulated gene expression in gingival fibroblasts, we hypothesized that TGF-β signaling is
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