Ilomastat
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Ilomastat
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CAS No:
142880-36-2
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Formula:
C20H28N4O4
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Chemical Name:
Ilomastat
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Synonyms:
Butanediamide,N4-hydroxy-N1-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)-,(2R)-;Butanediamide,N4-hydroxy-N1-[1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)-,[S-(R*,S*)]-;(2R)-N4-Hydroxy-N1-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)butanediamide;GM 6001;Galardin;Ilomastat;CS 610;(R)-N1-((S)-3-(1H-indol-3yl)-1-(methylamino)-1-oxopropan-2-yl)-N4-hydroxy-2-isobutylsuccinamide
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CAS No:
Description
Ilomastat (Galardin; GM6001) is a broad spectrum matrix metalloprotease (MMP) inhibitor, with Ki of 0.4 nM, 0.5 nM, 27 nM, 3.7 nM, 0.1 nM, 0.2 nM, 3.6 nM, 13.4 nM, 0.36 nM for MMP-1/2/3/7/8/9/12/14/26, respectively.
Ilomastat is an N-acyl-amino acid obtained by formal condensation of the carboxy group of (2R)-2-[2-(hydroxyamino)-2-oxoethyl]-4-methylpentanoic acid with the amino group of N-methyl-L-tryptophanamide. A cell permeable broad-spectrum matrix metalloproteinase (MMP) inhibitor It has a role as an EC 3.4.24.24 (gelatinase A) inhibitor, a neuroprotective agent, an anti-inflammatory agent, an antibacterial agent and an antineoplastic agent. It is a L-tryptophan derivative, a hydroxamic acid and a N-acyl-amino acid.
Ilomastat Use and Manufacturing
GM 6001 is a potent, reversible broad spectrum inhibitor of zinc-containing proteases, including matrix metalloproteinases (MMPs). It inhibits zinc-containing thermolysin and elastase from P. aeruginosa, both with Ki values of 20 nM. GM 6001 inhibits MMP-1, -2, -7, -8, -9, -12, -13, -14, -16, and -26 with Ki or IC50 values between 0.1 and 10 nM. It inhibits disintegrin and metalloproteinase domain-containing (ADAM) proteins ADAM9, ADAM10, ADAM12, and ADAM17 at nanomolar concentrations. It less potently inhibits lethal factor from B. anthracis anthrax lethal toxin (Ki = 2.74 μM). GM 6001 also impairs the growth of the human pathogen Chlamydia by inhibiting peptide deformylase, which contains iron rather than zinc (IC50 = 38 nM).
Computed Properties
Molecular Weight:388.5
XLogP3:0.9
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:9
Exact Mass:388.21105539
Monoisotopic Mass:388.21105539
Topological Polar Surface Area:123
Heavy Atom Count:28
Complexity:554
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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