ilomastat
(S-(R*,S*))-N(sup 4)-hydroxy-N(sup 1)-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylopropyl)butanediamide
 
Notes:
None found
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(2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide (Click)
CAS Number: 142880-36-2Picture of molecule
FDA UNII: I0403ML141
Nikkaji Web: J601.478J
XlogP3-AA: 0.90 (est)
Molecular Weight: 388.46796000
Formula: C20 H28 N4 O4
NMR Predictor: Predict (works with chrome or firefox)
Category: chelating agents
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 675.5 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: chelating agents
skin conditioning
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Suppliers:
EMD Millipore
For experimental / research use only.
GM 6001
Santa Cruz Biotechnology
For experimental / research use only.
GM 6001 ≥97%
Sigma-Aldrich: Sigma
For experimental / research use only.
(R)-N4-Hydroxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide >95% (HPLC)
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 132519
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide
Chemidplus: 0142880362
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References:
 (2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 132519
Pubchem (sid): 135089046
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEMBL: View
KEGG (GenomeNet): D03793
HMDB (The Human Metabolome Database): Search
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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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
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Articles:
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.
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