ChemicalBook--->CAS DataBase List--->154039-60-8

154039-60-8

154039-60-8 Structure

154039-60-8 Structure
IdentificationBack Directory
[Name]

Marimastat
[CAS]

154039-60-8
[Synonyms]

BB 2516
GI 5712
TA 2516
CS-1627
KB-R 8898
Marimastat
Marimistat
BB 2516; MARIMISTAT
Marimastat(BB-2516)
(2R,3S)-N1-((S)-3,3-diMethyl-1-(MethylaMino)-1-oxobutan-2-yl)-N4
(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)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N\',3-dihydroxy-2-(2-methylpropyl)butanediamide
Butanediamide, N4-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)-, (2S,3R)-
BB2516, (2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl] propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide
[EINECS(EC#)]

251-228-4
[Molecular Formula]

C15H29N3O5
[MDL Number]

MFCD00866242
[MOL File]

154039-60-8.mol
[Molecular Weight]

331.41
Chemical PropertiesBack Directory
[Melting point ]

148℃
[density ]

1.140±0.06 g/cm3(Predicted)
[RTECS ]

EJ6665000
[storage temp. ]

-20°C
[solubility ]

DMSO: ≥20mg/mL
[form ]

White solid
[pka]

9.44±0.40(Predicted)
[color ]

White to gray
[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
[InChIKey]

OCSMOTCMPXTDND-OUAUKWLOSA-N
[SMILES]

CNC(=O)[C@@H](NC(=O)[C@H](CC(C)C)[C@H](O)C(=O)NO)C(C)(C)C
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P261-P280a-P304+P340-P305+P351+P338-P405-P501a
[WGK Germany ]

3
[HS Code ]

29241990
[Storage Class]

11 - Combustible Solids
Hazard InformationBack Directory
[Uses]

Antineoplastic (matrix metalloproteinase inhibitor).
[Definition]

ChEBI: Marimastat is a secondary carboxamide resulting from the foraml condensation of the carboxy group of (2R)-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the alpha-amino group of N,3-dimethyl-L-valinamide. It has a role as an antineoplastic agent and a matrix metalloproteinase inhibitor. It is a secondary carboxamide and a hydroxamic acid.
[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.
[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
[storage]

Store at -20°C
Spectrum DetailBack Directory
[Spectrum Detail]

Marimastat(154039-60-8)MS
Marimastat(154039-60-8)1HNMR
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