Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C20H28N4O4 |
| Molecular Weight | 388.4607 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(=O)[C@H](CC1=CNC2=C1C=CC=C2)NC(=O)[C@H](CC(C)C)CC(=O)NO
InChI
InChIKey=NITYDPDXAAFEIT-DYVFJYSZSA-N
InChI=1S/C20H28N4O4/c1-12(2)8-13(10-18(25)24-28)19(26)23-17(20(27)21-3)9-14-11-22-16-7-5-4-6-15(14)16/h4-7,11-13,17,22,28H,8-10H2,1-3H3,(H,21,27)(H,23,26)(H,24,25)/t13-,17+/m1/s1
| Molecular Formula | C20H28N4O4 |
| Molecular Weight | 388.4607 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Ilomastat (also known as galardin or GM 6001) is a broad-spectrum matrix metalloproteinase inhibitor. It is a member of the hydroxamic acid class of reversible metallopeptidase inhibitors. The hydroxamic acid binds the catalytic zinc(2+) ion in a bidentate manner, blocking substrate access to the active site and rendering the metal incapable of peptide hydrolysis. Preclinical studies have shown that ilomastat can inhibit conjunctival scarring after glaucoma filtration surgery in rabbits, in lens capsules following simulated cataract surgery, and in models of vitreoretinal contraction.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL332 |
3.3 nM [IC50] | ||
Target ID: CHEMBL333 |
10.0 nM [IC50] | ||
Target ID: CHEMBL283 |
7.0 nM [IC50] | ||
Target ID: CHEMBL4073 |
33.0 nM [IC50] | ||
Target ID: CHEMBL4588 |
9.7 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of human skin fibroblast collagenase, thermolysin, and Pseudomonas aeruginosa elastase by peptide hydroxamic acids. | 1992 Aug 11 |
|
| Decreased expression of membrane IL-5 receptor alpha on human eosinophils: II. IL-5 down-modulates its receptor via a proteinase-mediated process. | 2002 Dec 1 |
|
| Tamoxifen induces apoptosis in Fas+ tumor cells by upregulating the expression of Fas ligand. | 2003 Apr |
|
| Heparin-binding epidermal growth factor cleavage mediates zinc-induced epidermal growth factor receptor phosphorylation. | 2004 Apr |
|
| Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors. | 2004 Jan 5 |
|
| Metalloproteinases mediate mucin 5AC expression by epidermal growth factor receptor activation. | 2005 Feb 15 |
|
| Epidermal growth factor receptor-dependent and -independent pathways in hydrogen peroxide-induced mitogen-activated protein kinase activation in cardiomyocytes and heart fibroblasts. | 2005 Mar |
|
| Methylmercury induces activation of Notch signaling. | 2006 Dec |
|
| Effects of alpha1D-adrenergic receptors on shedding of biologically active EGF in freshly isolated lacrimal gland epithelial cells. | 2006 Nov |
|
| Differential modulation of Alzheimer's disease amyloid beta-peptide accumulation by diverse classes of metal ligands. | 2007 Nov 1 |
|
| Discovery and characterization of a novel inhibitor of matrix metalloprotease-13 that reduces cartilage damage in vivo without joint fibroplasia side effects. | 2007 Sep 21 |
|
| Acrolein-activated matrix metalloproteinase 9 contributes to persistent mucin production. | 2008 Apr |
|
| Expression profiles of matrix metalloproteinase 9 in teleost fish provide evidence for its active role in initiation and resolution of inflammation. | 2008 Dec |
|
| Chronic treatment of astrocytes with therapeutically relevant fluoxetine concentrations enhances cPLA2 expression secondary to 5-HT2B-induced, transactivation-mediated ERK1/2 phosphorylation. | 2009 Nov |
|
| Matrix metalloproteinase-14 mediates a phenotypic shift in the airways to increase mucin production. | 2009 Nov 1 |
|
| ATP induced microglial cell migration through non-transcriptional activation of matrix metalloproteinase-9. | 2010 Feb |
|
| Ovarian steroids, mitogen-activated protein kinases, and/or aspartic proteinases cooperate to control endometrial remodeling by regulating gene expression in the stroma and glands. | 2010 Sep |
|
| Zinc-triggered induction of tissue plasminogen activator by brain-derived neurotrophic factor and metalloproteinases. | 2011 Sep |
|
| Proteolysis controls endogenous substance P levels. | 2013 |
|
| Amyloid-β-induced matrix metalloproteinase-9 secretion is associated with retinal pigment epithelial barrier disruption. | 2013 May |
Patents
Sample Use Guides
Rabbits received 0.1 mL of 100 uM ilomastat.
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:02:32 GMT 2023
by
admin
on
Sat Dec 16 17:02:32 GMT 2023
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| Record UNII |
I0403ML141
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| Record Status |
Validated (UNII)
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| Record Version |
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FDA ORPHAN DRUG |
63991
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NCI_THESAURUS |
C1970
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GM6001
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SUB08133MIG
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C96286
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137236
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C119203
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DB02255
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142880-36-2
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GG-32
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CHEMBL19611
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1368877
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I0403ML141
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7383
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132519
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100000083685
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DTXSID0046353
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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TARGET -> INHIBITOR |
IC50
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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