Basic information
- CAS
142880-36-2- Standard SMILES
CNC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@@H](CC(=O)NO)CC(C)C- InChIKey
NITYDPDXAAFEIT-DYVFJYSZSA-N- Molecular formula
- C20H28N4O4
- Average molar mass
- 388.5 g/mol
- Monoisotopic mass
- 388.21105539
Overview
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 antibacterial agent, an antineoplastic agent, a neuroprotective agent, an anti-inflammatory agent and an EC 3.4.24.24 (gelatinase A) inhibitor. It is a hydroxamic acid, a L-tryptophan derivative and a N-acyl-amino acid.
Names & identifiers
- Preferred name
- Ilomastat
- IUPAC
- (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide
- English name
- Ilomastat
- Molecular formula
- C20H28N4O4
- Molecular weight
- 388.46
Names & synonyms
Ilomastat142880-36-2GalardinGM6001GM 6001CS 610DTXSID0046353GM-6001CS-610I0403ML141(R)-N(sup 1)-Hydroxy-N-((S)-2-indol-3-yl-1-(methylcarbamoyl)ethyl)-2-isobutylsuccinamide(S-(R*,S*))-N(sup 4)-Hydroxy-N(sup 1)-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylopropyl)butanediamide
Show more names
CS-1405SANTACRUZllomastatsc-203979AIlloMastatgalardin tmIlomastat, >=98%GM 6001 IlomastatIlomastat (GM 6001)Galardin CS 610
DTXCID8026353CHEBI:137236ilomastatum(2R)-N'-hydroxy-N-((2S)-3-(1H-indol-3-yl)-1-methylamino-1-oxopropan-2-yl)-2-(2-methylpropyl)butanediamide(2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-methylamino-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamideRefChem:790596N'-hydroxy-N-((S)-2-indol-3-yl-1-(methylcarbamoyl)ethyl)-2-isobutylsuccinamide(2R)-N'-hydroxy-N-((1S)-2-(1H-indol-3-yl)-1-(methylcarbamoyl)ethyl)-2-(2-methylpropyl)butanediamide
Database identifiers
Properties
Computed structural properties
- XLogP
- 0.9
- Topological polar surface area
- 123 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 9
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 554
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.04
Physicochemical properties
- Density
- 1.228 · 1.228±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 100 % · Soluble in DMSO, and 100% ethanol.
- pka
- 9.16 · 9.16±0.20(Predicted)
- form
- Off-white solid
- color
- White
- Sensitive
- Moisture Sensitive
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
- Cosmetics Ingredients Functions
- CHELATINGSKIN CONDITIONING
- InChIKey
- NITYDPDXAAFEIT-DYVFJYSZSA-N
- SMILES
- CNC([C@@H](NC([C@@H](C(C)C)CC(NC)=O)=O)CC1=CNC2=CC=CC=C21)=O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29339900
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302+H312+H332-H315-H319
- Precautionary statements
- P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationCompounds that inhibit the enzyme activity or activation of MATRIX METALLOPROTEINASES.
Applications
DescriptionIlomastat (142880-36-2) is a potent pan-specific inhibitor of matrix metalloproteinases (MMPs).1 Ki values have been reported for the following human MMPs: MMP-1, 0.4nM; MMP-2, 0.5nM; MMP-3, 27nM; MMP-7, 3.7nM; MMP-8, 0.1nM; MMP-9, 0.2nM; MMP-12, 3.6nM; MMP-14, 13.4nM; MMP-26, 0.36nM.2-4 Also inhibits MMP-10, MMP-13, MMP-15, MMP-17, MMP-20, MMP-21, TACE and ADAM19.
UsesGM 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).
UsesIlomastat is a metalloprotease inhibitor.
General DescriptionA cell-permeable, potent broad-spectrum hydroxamic acid inhibitor of matrix metalloproteinases (MMPs). [Ki = 0.4 nM for skin fibroblast collagenase (MMP-1); Ki = 0.5 nM for gelatinase A (MMP-2); Ki = 27 nM for stromelysin (MMP-3); Ki = 0.1 nM for neutrophil collagenase (MMP-8); and Ki = 0.2 nM for gelatinase B (MMP-9)]. Also prevents the release of TNF-α in vivo and in vitro and abrogates endotoxin-induced lethality in mice.
Suppliers100 total
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…