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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
Structure of ILOMASTAT

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

HIDE SMILES / InChI

Description

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.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.3 nM [IC50]
10.0 nM [IC50]
7.0 nM [IC50]
33.0 nM [IC50]
9.7 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Rabbits received 0.1 mL of 100 uM ilomastat.
Route of Administration: Other
In Vitro Use Guide
Ilomastat inhibits human skin fibroblast collagenase with Ki of 0.4 nM when assayed with a synthetic thioester substrate at pH 6.5, with 50-fold selectivity over two bacterial enzymes, thermolysin, and Pseudomonas aeruginosa elastase.