ilomastat
(S-(R*,S*))-N(sup 4)-hydroxy-N(sup 1)-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylopropyl)butanediamide
Identification
| Name | ilomastat |
| IUPAC | (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide |
| CAS Number | 142880-36-2 |
| FDA UNII | I0403ML141 |
| Molecular Formula | C20 H28 N4 O4 |
| Molecular Weight | 388.46796000 |
| Nikkaji Number | J601.478J |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 675.5 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | chelating agents |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | chelating agents |
| Recommendation for ilomastat usage levels up to | not for fragrance use. |
| Recommendation for ilomastat flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
butanediamide, N4-hydroxy-N1-(1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)-, (S-(R*,S*))-
galardin
(S-(R*,S*))-N(sup 4)-
hydroxy-N(sup 1)-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylopropyl)butanediamide
(R)-N(sup 1)-
hydroxy-N-((S)-2-indol-3-yl-1-(methylcarbamoyl)ethyl)-2-isobutylsuccinamide
(2R)-N'-
hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide
PubMed:
Association of MMP-8 with obesity, smoking and insulin resistance.
PubMed:
Selective non-zinc binding MMP-2 inhibitors: Novel benzamide Ilomastat analogs with anti-tumor metastasis.
PubMed:
ADAMTS13 and 15 are not regulated by the full length and N-terminal domain forms of TIMP-1, -2, -3 and -4.
PubMed:
Bisphenol A and Related Alkylphenols Exert Nongenomic Estrogenic Actions Through a G Protein-Coupled Estrogen Receptor 1 (Gper)/Epidermal Growth Factor Receptor (Egfr) Pathway to Inhibit Meiotic Maturation of Zebrafish Oocytes.
PubMed:
Sequential Therapy with Saratin, Bevacizumab and Ilomastat to Prolong Bleb Function following Glaucoma Filtration Surgery in a Rabbit Model.
PubMed:
Antibody-based exosite inhibitors of ADAMTS-5 (aggrecanase-2).
PubMed:
Involvement of epidermal growth factor receptors and mitogen-activated protein kinase in progestin-induction of sperm hypermotility in Atlantic croaker through membrane progestin receptor-alpha.
PubMed:
Reducing tumor growth and angiogenesis using a triple therapy measured with Contrast-enhanced ultrasound (CEUS).
PubMed:
Matrix metalloproteinases regulate extracellular levels of SDF-1/CXCL12, IL-6 and VEGF in hydrogen peroxide-stimulated human periodontal ligament fibroblasts.
PubMed:
Near-infrared triple-helical peptide with quenched fluorophores for optical imaging of MMP-2 and MMP-9 proteolytic activity in vivo.
PubMed:
Mesenchymal to amoeboid transition is associated with stem-like features of melanoma cells.
PubMed:
Extra-cellular matrix proteins induce matrix metalloproteinase-1 (MMP-1) activity and increase airway smooth muscle contraction in asthma.
PubMed:
Moderate inhibition of myocardial matrix metalloproteinase-2 by ilomastat is cardioprotective.
PubMed:
Molecular dynamic simulations of ocular tablet dissolution.
PubMed:
Proteolysis controls endogenous substance P levels.
PubMed:
Matrix metalloproteinase inhibition protects CyPD knockout mice independently of RISK/mPTP signalling: a parallel pathway to protection.
PubMed:
Initial characterization of a dually radiolabeled peptide for simultaneous monitoring of protein targets and enzymatic activity.
PubMed:
Functional characterization of the Mycobacterium tuberculosis zinc metallopeptidase Zmp1 and identification of potential substrates.
PubMed:
Characterisation of ilomastat for prolonged ocular drug release.
PubMed:
Concanavalin-A-induced autophagy biomarkers requires membrane type-1 matrix metalloproteinase intracellular signaling in glioblastoma cells.
PubMed:
Preparation and in vitro evaluation of an ilomastat microemulsion gel by a self-microemulsifying system.
PubMed:
Novel Gd(III)-based probes for MR molecular imaging of matrix metalloproteinases.
PubMed:
Matrix metalloproteinase inhibitor attenuates cochlear lateral wall damage induced by intratympanic instillation of endotoxin.
PubMed:
Effects of platelet-rich and -poor plasma on the reparative response of gingival fibroblasts.
PubMed:
Involvement of epidermal growth factor receptor signaling in estrogen inhibition of oocyte maturation mediated through the G protein-coupled estrogen receptor (Gper) in zebrafish (Danio rerio).
PubMed:
LIM kinase1 modulates function of membrane type matrix metalloproteinase 1: implication in invasion of prostate cancer cells.
PubMed:
Relative roles of doxycycline and cation chelation in endothelial glycan shedding and adhesion of leukocytes.
PubMed:
Sulfur mustard-induced pulmonary injury: therapeutic approaches to mitigating toxicity.
PubMed:
Development of a novel tumor-targeted vascular disrupting agent activated by membrane-type matrix metalloproteinases.
PubMed:
Role of iNOS and peroxynitrite-matrix metalloproteinase-2 signaling in myocardial late preconditioning in rats.
PubMed:
Matrix metalloproteinase inhibition enhances the rate of nerve regeneration in vivo by promoting dedifferentiation and mitosis of supporting schwann cells.
PubMed:
Airway smooth muscle remodels pericellular collagen fibrils: implications for proliferation.
PubMed:
Anti-inflammatory effects of formoterol and ipratropium bromide against acute cadmium-induced pulmonary inflammation in rats.
PubMed:
Inhibition of glycan shedding and leukocyte-endothelial adhesion in postcapillary venules by suppression of matrixmetalloprotease activity with doxycycline.
PubMed:
The role of an MMP inhibitor in the regulation of mechanical tension by Dupuytren's disease fibroblasts.
PubMed:
Matrix metalloprotease expressions in both reperfusion lung injury and oleic acid lung injury models and the protective effects of ilomastat.
PubMed:
Use of a three-dimensional cell culture model to study airway smooth muscle-mast cell interactions in airway remodeling.
PubMed:
Fibrillar collagen clamps lung mesenchymal cells in a nonproliferative and noncontractile phenotype.
PubMed:
Matrix metalloproteinase inhibition reduces contraction by dupuytren fibroblasts.
PubMed:
Matrix metalloproteinase inhibitors reduce collagen gel contraction and alpha-smooth muscle actin expression by periodontal ligament cells.
PubMed:
Evaluation of protease inhibitors and an antioxidant for treatment of sulfur mustard-induced toxic lung injury.
PubMed:
Protective effect of ilomastat on trinitrobenzenesulfonic acid-induced ulcerative colitis in rats.
PubMed:
Prostaglandin E2 exerts catabolic effects in osteoarthritis cartilage: evidence for signaling via the EP4 receptor.
PubMed:
Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with improved selectivity.
PubMed:
The effect of stress-deprivation and cyclic loading on the TIMP/MMP ratio in tendon cells: an in vitro experimental study.
PubMed:
CD44-epidermal growth factor receptor interaction mediates hyaluronic acid-promoted cell motility by activating protein kinase C signaling involving Akt, Rac1, Phox, reactive oxygen species, focal adhesion kinase, and MMP-2.
PubMed:
Dense collagen matrix accelerates osteogenic differentiation and rescues the apoptotic response to MMP inhibition.
PubMed:
Identification of MMP-12 inhibitors by using biosensor-based screening of a fragment library.
PubMed:
Bone sialoprotein binding to matrix metalloproteinase-2 alters enzyme inhibition kinetics.
PubMed:
C-FLIP promotes the motility of cancer cells by activating FAK and ERK, and increasing MMP-9 expression.
PubMed:
Human laminin-332 degradation by Candida proteinases.
PubMed:
Simultaneous presence of unsaturation and long alkyl chain at P'1 of Ilomastat confers selectivity for gelatinase A (MMP-2) over gelatinase B (MMP-9) inhibition as shown by molecular modelling studies.
PubMed:
A sequential, multiple-treatment, targeted approach to reduce wound healing and failure of glaucoma filtration surgery in a rabbit model (an American Ophthalmological Society thesis).
PubMed:
Matrix metalloproteinase inhibitors prevent a decrease in the mechanical properties of stress-deprived tendons: an in vitro experimental study.
PubMed:
MT1-MMP down-regulates the glucose 6-phosphate transporter expression in marrow stromal cells: a molecular link between pro-MMP-2 activation, chemotaxis, and cell survival.
PubMed:
Collagen I and thrombin activate MMP-2 by MMP-14-dependent and -independent pathways: implications for airway smooth muscle migration.
PubMed:
The role of matrix metalloproteinases in infant traumatic brain injury.
PubMed:
An inhaled matrix metalloprotease inhibitor prevents cigarette smoke-induced emphysema in the mouse.
PubMed:
Cooperation of matrix metalloproteinases with the RhoA/Rho kinase and mitogen-activated protein kinase kinase-1/extracellular signal-regulated kinase signaling pathways is required for the sphingosine-1-phosphate-induced mobilization of marrow-derived stromal cells.
PubMed:
Cell-cell contact activation of fibroblasts increases the expression of matrix metalloproteinases.
PubMed:
Oxygen radicals and matrix metalloproteinases mediate reperfusion liver injury.
PubMed:
Metalloproteinase inhibitors, nonantimicrobial chemically modified tetracyclines, and ilomastat block Bacillus anthracis lethal factor activity in viable cells.
PubMed:
Hyperlipidemia attenuates the infarct size-limiting effect of ischemic preconditioning: role of matrix metalloproteinase-2 inhibition.
PubMed:
In vitro evaluation of the angiostatic potential of drugs using an endothelialized tissue-engineered connective tissue.
PubMed:
Prolonged antiscarring effects of ilomastat and MMC after experimental glaucoma filtration surgery.
PubMed:
Cardiac morphogenesis: matrix metalloproteinase coordination of cellular mechanisms underlying heart tube formation and directionality of looping.
PubMed:
Inflammatory proteases in chronic otitis externa.
PubMed:
Poly(ADP-ribose) polymerase-1 promotes microglial activation, proliferation, and matrix metalloproteinase-9-mediated neuron death.
PubMed:
Evidence for disulfide involvement in the regulation of intramolecular autolytic processing by human adamalysin19/ADAM19.
PubMed:
Flavonoids promote cell migration in nontumorigenic colon epithelial cells differing in Apc genotype: implications of matrix metalloproteinase activity.
PubMed:
Activity-based probes for the proteomic profiling of metalloproteases.
PubMed:
MMP inhibition prevents human lens epithelial cell migration and contraction of the lens capsule.
PubMed:
A novel strategy for designing specific gelatinase A inhibitors: potential use to control tumor progression.
PubMed:
Hyaluronan cell surface binding is induced by type I collagen and regulated by caveolae in glioma cells.
PubMed:
MMPs inhibitors: new succinylhydroxamates with selective inhibition of MMP-2 over MMP-3.
PubMed:
Galardin (GM 6001), a broad-spectrum matrix metalloproteinase inhibitor, blocks bombesin- and LPA-induced EGF receptor transactivation and DNA synthesis in rat-1 cells.
PubMed:
Protease inhibitors alpha1-antitrypsin and ilomastat are not ototoxic in the chinchilla.
PubMed:
Enhancement by neutrophils of collagen degradation by corneal fibroblasts.
PubMed:
Effects of matrix metalloproteinase inhibitors on bone resorption and orthodontic tooth movement.
PubMed:
Alpha 1-antitrypsin and ilomastat inhibit inflammatory proteases present in human middle ear effusions.
PubMed:
Matrix metalloproteinase regulation of sphingosine-1-phosphate-induced angiogenic properties of bone marrow stromal cells.
PubMed:
Matrix metalloproteinase inhibition modulates fibroblast-mediated matrix contraction and collagen production in vitro.
PubMed:
Matrix metalloproteinase inhibition modulates postoperative scarring after experimental glaucoma filtration surgery.
PubMed:
Human corneal epithelial cells require MMP-1 for HGF-mediated migration on collagen I.
PubMed:
Metalloproteinase shedding of Fas ligand regulates beta-amyloid neurotoxicity.
PubMed:
Shedding of kidney injury molecule-1, a putative adhesion protein involved in renal regeneration.
PubMed:
The electrical resistance breakdown assay determines the role of proteinases in tumor cell invasion.
PubMed:
Membrane-type matrix metalloproteinases mediate curcumin-induced cell migration in non-tumorigenic colon epithelial cells differing in Apc genotype.
PubMed:
Involvement of matrix metalloproteinases in the adipose conversion of 3T3-L1 preadipocytes.
PubMed:
Topical synthetic inhibitor of matrix metalloproteinases delays epidermal regeneration of human wounds.
PubMed:
Mutation analysis of membrane type-1 matrix metalloproteinase (MT1-MMP). The role of the cytoplasmic tail Cys(574), the active site Glu(240), and furin cleavage motifs in oligomerization, processing, and self-proteolysis of MT1-MMP expressed in breast carcinoma cells.
PubMed:
Matrix metalloproteinases and their inhibitors regulate in vitro ureteric bud branching morphogenesis.
PubMed:
Determination of matrix metalloproteinase activity using biotinylated gelatin.
PubMed:
Tissue inhibitor of metalloproteinase-2 stimulates mesenchymal growth and regulates epithelial branching during morphogenesis of the rat metanephros.