444289

Marimastat

An orally active peptidyl hydroxamate-based broad-spectrum MMP inhibitor that targets both the substrate binding site and the active-site Zn²⁺.

• Synonym(s): Marimastat, (2S,3R)-N⁴-((1S)-2,2-Dimethyl-1-((methylamino)carbonyl)propyl)-N¹,2-hydroxy-3-(2-methylpropyl)butanediamide, BB-2516
• Empirical Formula (Hill Notation): C₁₅H₂₉N₃O₅
• CAS Number: 154039-60-8
• Molecular Weight: 331.41
• UNSPSC Code: 12352200
• NACRES: NA.77
• MDL number: MFCD00866242
• Assay: ≥98% (NMR)
• Form: solid
• Storage condition: OK to freeze, protect from light

Properties

• Quality Segment: 100
• assay: ≥98% (NMR)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: white
• solubility: DMSO: 15 mg/mL
• shipped in: ambient
• storage temp.: 2-8°C
• SMILES string: N(O)C(=O)[C@@H](O)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)(C)C)C(=O)NC
• 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

Description

General description

An orally active peptidyl hydroxamate-based broad-spectrum MMP inhibitor (IC₅₀ in nM = 5, 6, 200, 20, 2, 1.8 and 3.8 for MMP-1, -2, -3, -7, -8, -14 and TACE, respectively) that targets both the substrate binding site and the active-site Zn²⁺. Marimastate is widely used in studying the involvement of MMPs in various cellular and pathological processes both in vitro and in vivo.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Hansen, H.P., et al. 2002. Int. J. Cancer98, 210.
Tsuji, F., et al. 2002. Cytokine17, 294.
Barlaam, B., et al. 1999. J. Med. Chem.42, 4890.
Whittaker, M., et al. 1999. Chem. Rev.99, 2735.
Rasmussen, H.S., and McCann, P.P. 1997. Pharmacol. Ther.75, 69.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable