154039-60-8

Basic information

• Product Name: Marimastat
• Synonyms: Marimastat;(2R,3S)-N1-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-N4,3-dihydroxy-2-isobutylsuccinamide;(2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide;(2R,3S)-N1-((S)-3,3-diMethyl-1-(MethylaMino)-1-oxobutan-2-yl)-N4;BB 2516;GI 5712;KB-R 8898;TA 2516
• CAS NO: 154039-60-8
• Molecular Formula: C15H29N3O5
• Molecular Weight: 331.41
• Product Categories: API
• Mol File: 154039-60-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 148℃
• Appearance: /
• Density: 1.14 g/cm³
• Refractive Index: 1.498
• Storage Temp.: Store at -20°C
• Solubility: DMSO: ≥20mg/mL
• PKA: 9.44±0.40(Predicted)
• CAS DataBase Reference: Marimastat(CAS DataBase Reference)
• NIST Chemistry Reference: Marimastat(154039-60-8)
• EPA Substance Registry System: Marimastat(154039-60-8)

Safety Data

• WGK Germany: 3
• RTECS: EJ6665000
• Hazardous Substances Data: 154039-60-8(Hazardous Substances Data)

Usage

Description

Marimastat is an orally active peptidyl hydroxamate-based broad-spectrum matrix metalloproteinase (MMP) inhibitor. It targets both the substrate binding site and the active-site Zn2+ of MMPs, with an IC50 in the nanomolar range for various MMPs. Marimastat is widely used in studying the involvement of MMPs in various cellular and pathological processes both in vitro and in vivo.

Uses

Used in Antineoplastic Applications:
Marimastat is used as a matrix metalloproteinase inhibitor for the treatment of various cancers. It acts as an inhibitor of metalloproteinase 2/9 (MMP2/9), metalloproteinase, and metalloproteinase 10 (MMP10), playing a crucial role in modulating the progression of cancer and other pathological occurrences such as arthritis and atherosclerosis.
Used in Research Applications:
Marimastat is used as a research tool to study the effects of MMP inhibition on exercise-mediated interleukin-6 (IL-6) release in mice, protease activity in Pseudomonas aeruginosa cultures, and the binding of monoclonal antibody H3 to MMP10. This helps in understanding the role of MMPs in various cellular and pathological processes.

Biological Activity

Broad spectrum inhibitor of matrix metalloprotease (MMP) (IC 50 values are 3, 5, 6, 9 and 13 nM for MMP-9, MMP-1, MMP-2, MMP-14 and MMP-7 respectively). In vivo inhibits peritoneal dissemination of human gastric cancer cells through inhibition of tumor angiogenesis.

Biochem/physiol Actions

Marimastat is a broad spectrum matrix metalloprotease (MMP) inhibitor

InChI:InChI=1/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

Upstream product

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• 89226-12-0 (S)-2-amino-N,3,3-trimethylbutanamide 
• 200866-75-7 (2S,3R)-3-((S)-2,2-Dimethyl-1-methylcarbamoyl-propylcarbamoyl)-2-hydroxy-5-methyl-hexanoic acid methyl ester 

Relevant articles and documents

An improved synthesis of the broad spectrum matrix metalloprotease inhibitor marimastat

A considerably shortened synthesis of the broad spectrum matrix metalloproteinase (MMP) inhibitor marimastat has been achieved by a direct hydroxylamino ring opening of a key acetonide intermediate. (C) 2000 Elsevier Science Ltd.