Compound: Marimastat
SMILES: O=C(NC)[C@@H](NC(=O)[C@@H]([C@H](O)C(=O)NO)CC(C)C)C(C)(C)C
InChIKey: OCSMOTCMPXTDND-OUAUKWLOSA-N
Synonyms: Marimastat, 154039-60-8, BB-2516, BB 2516, BB2516, D5EQV23TDS, NSC-719333, GI5712, KB-R 8898, TA2516, GI-5712, TA-2516, (2S,3R)-3-(((1S)-2,2-Dimethyl-1-(methylcarbamoxy)propyl)carboyl)-2-hydroxy-5-methylhexanohydroxamic acid, CHEBI:50662, DTXSID20165524, NSC689451, NSC719333, Marimistat, (2S,3R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-N',2-dihydroxy-3-(2-methylpropyl)butanediamide, marimastatum, (2S,3R)-N-((1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl)-N',2-dihydroxy-3-(2-methylpropyl)butanediamide, RefChem:810621, DTXCID3088015, (2S,3R)-3-((S)-(2,2-Dimethyl-1-(methylcarbamoyl) propyl)carbamoyl)-2-hydroxy-5-methylhexanohydroxamic acid, Marimastat (BB-2516), (2R,3S)-N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N',3-dihydroxy-2-(2-methylpropyl)butanediamide, (2R,3S)-N1-((S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-N4,3-dihydroxy-2-isobutylsuccinamide, MFCD00866242, BB2516;TA2516, CHEMBL279785, Marimastat [USAN], TA 2516, (2S,3R)-3-(((1S)-2,2-Dimethyl-1-(methylcarbamoyl)propyl)carbamoyl)-2-hydroxy-5-methylhexanohydroxamic acid, (2S,3R)-N(4)-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N(1),2-dihydroxy-3-(2-methylpropyl)butanediamide, (2R)-N-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-2-[(1S)-1-hydroxy-2-(hydroxyamino)-2-oxo-ethyl]-4-methyl-pentanamide, (2s,3r)-N~4~-[(1s)-2,2-Dimethyl-1-(Methylcarbamoyl)propyl]-N~1~,2-Dihydroxy-3-(2-Methylpropyl)butanediamide, Butanediamide, N4-((1S)-2,2-dimethyl-1-((methylamino)carbonyl)propyl)-N1,2-dihydroxy-3-(2-methylpropyl)-, (2S,3R)-, Butanediamide, N4-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)-, (2S,3R)-, SMR002530328, Marimastat (USAN/INN), UNII-D5EQV23TDS, Marimastat [USAN:INN:BAN], (2S,3R)-3-[[(1S)-2,2-Dimethyl-1-(methylcarbamoyl)propyl]carbamoyl]-2-hydroxy-5-methylhexanohydroxamic acid, Butaneamide,2-dimethyl-1-[(methylamino)carbonyl]propyl]- N1,2-dihydroxy-3-(2-methylpropyl)-, (2S,3R)-, 3hy7, MARIMASTAT [MI], MARIMASTAT [INN], D03795, MARIMASTAT [MART.], MARIMASTAT [WHO-DD], SCHEMBL34033, MLS003899230, MLS006010669, cid_119031, GTPL5220, orb1300377, Marimastat, >=98% (HPLC), EX-A643, GLXC-06760, BDBM50063917, s7156, AKOS024457206, CCG-267821, CS-3456, DB00786, GI 5712, NSC 719333, NSC-689451, Marimastat - CAS 154039-60-8, (2S,3R)-N'-[(1S)-2,2-dimethyl-1-(methylcarbamoyl)propyl]-N,2-dihydroxy-3-(2-methylpropyl)butanediamide, (2S,3R)-N4-[(1S)-2,2-Dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)butanediamide, AC-35828, AS-57129, Butanediamide, N(sup 4)-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-N(sup 1),2-dihydroxy-3-(2-methylpropyl)-, (2S-(N(sup 4)(R*),2R*,3S*))-, Butanediamide, N4-(2,2-dimethyl-1-((methylamino)carbonyl)propyl)-N1,2-dihydroxy-3-(2-methylpropyl)-, (2S-(N4(R*),2R*,3S*))-, FM161188, HY-12169, NS00068619, Q6763659, BRD-K21396683-001-04-8, (2S,3R)-N~4~-[(2S)-3,3-Dimethyl-1-(methylamino)-1-oxobutan-2-yl]-N~1~,2-dihydroxy-3-(2-methylpropyl)butanediamide, BUTANEDIAMIDE, N(SUP 4)-(2,2-DIMETHYL-1-((METHYLAMINO)CARBONYL)PROPYL)-N1,2-DIHYDROXY-3-(2-METHYLPROPYL)-, (2S-(N4(R*),2R*,3S*))-
Theoretical properties:
molecular_formula: C15H29N3O5
molecular_weight: 331.41 g/mol
exact_mass: 331.21072103 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 8
heavy_atom_count: 23
topological_polar_surface_area: 128 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 3.38e+00 g/L
Descriptions:
pubchem: 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.
chebi: A secondary carboxamide resulting from the foraml condensation of the carboxy group of (2<i>R</i>)-2-[(1<i>S</i>)-1-hydroxy-2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the α-amino group of <em>N</em>,3-dimethyl-<small>L</small>-valinamide.
chembl: MARIMASTAT is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Marimastat was a proposed antineoplastic drug developed by British Biotech. It acted as a broad-spectrum matrix metalloproteinase inhibitor.
Marimastat performed poorly in clinical trials, and development was terminated. This may be, however, a result of targeting cancer at too late of a stage. This is supported by the fact that MMP inhibitors have more recently been shown in animal models to be more effective in earlier stages of cancers. (Effects of angiogenesis inhibitors on multistage carcinogenesis in mice. Science 284, 808–812. Bergers, G., Javaherian, K., Lo, K.-M., Folkman, J., and Hanahan, D. (1999)).