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M2699

Sigma-Aldrich

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
MDL number:
MFCD00866242
UNSPSC Code:
12352200
PubChem Substance ID:
329817950
NACRES:
NA.77

Product Name

Marimastat, ≥98% (HPLC)

Quality Level

100

Assay

≥98% (HPLC)

form

solid

solubility

DMSO: ≥20 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

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

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

InChI key

OCSMOTCMPXTDND-OUAUKWLOSA-N

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000394101
0000333793
0000333793
0000394101
0000237518

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J Thomas Peterson
Cardiovascular research, 69(3), 677-687 (2006-01-18)
At least 56 matrix metalloproteinase (MMP) inhibitors have been pursued as clinical candidates since the late 1970's when the first drug discovery program targeting this enzyme family began. Some of these clinical candidates were pursued for multiple indications. However, the
Nicholas J Youngman et al.
Molecules (Basel, Switzerland), 27(5) (2022-03-11)
Snakebite remains a significant public health burden globally, disproportionately affecting low-income and impoverished regions of the world. Recently, researchers have begun to focus on the use of small-molecule inhibitors as potential candidates for the neutralisation of key snake venom toxins
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
Timothy W Failes et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 13(10), 2974-2982 (2006-12-16)
We report a potential means of selectively delivering matrix metalloproteinase (MMP) inhibitors to target tumour sites by use of a bioreductively activated Co(III) carrier system. The carrier, comprising a Co(III) complex of the tripodal ligand tris(methylpyridyl)amine (tpa), was investigated with
Victor A Levin et al.
Journal of neuro-oncology, 78(3), 295-302 (2006-04-26)
Because raised matrix metalloprotease (MMP) levels are associated with glioma invasion and angiogenesis, we tested the efficacy of marimastat (MT) an orally active drug that can reduce MMP levels, in patients with gliomas. A total of 162 patients with intracranial
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