Ilomastat

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Identification

Generic Name

Ilomastat

DrugBank Accession Number

DB02255

Background

Ilomastat is a broad-spectrum matrix metalloproteinase inhibitor.

Type

Small Molecule

Groups

Experimental

Structure

Similar Structures

Weight: Average: 388.4607
Monoisotopic: 388.211055404
Chemical Formula: C₂₀H₂₈N₄O₄

Synonyms

(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
Ilomastat

External IDs

CS 610
GM 6001
GM-6001
GM6001

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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings

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Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
AInterstitial collagenase	inhibitor	Humans
AMatrix metalloproteinase-14	inhibitor	Humans
ANeutrophil collagenase	inhibitor	Humans
A72 kDa type IV collagenase	inhibitor	Humans
AStromelysin-1	inhibitor	Humans
AMatrix metalloproteinase-9	inhibitor	Humans
AMacrophage metalloelastase	inhibitor	Humans
ACollagenase 3	inhibitor	Humans
ALethal factor	inhibitor	Bacillus anthracis
UDisintegrin and metalloproteinase domain-containing protein 28	Not Available	Humans
UAggrecan core protein	Not Available	Humans

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions: This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions: Not Available

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International/Other Brands: Galardin

Chemical Identifiers

UNII: I0403ML141
CAS number: 142880-36-2
InChI Key: NITYDPDXAAFEIT-DYVFJYSZSA-N
InChI: 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
IUPAC Name: (2R)-N'-hydroxy-N-[(1S)-2-(1H-indol-3-yl)-1-(methylcarbamoyl)ethyl]-2-(2-methylpropyl)butanediamide
SMILES: CNC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)[C@H](CC(C)C)CC(=O)NO

References

General References

Not Available

External Links

KEGG Drug: D03793
PubChem Compound: 132519
PubChem Substance: 46506673
ChemSpider: 117009
BindingDB: 50062351
ChEBI: 137236
ChEMBL: CHEMBL19611
ZINC: ZINC000003780014
PDBe Ligand: GM6
Wikipedia: Ilomastat

PDB Entries

1pwu / 2dw0 / 2dw1 / 2e3x / 2erp / 4pkw

Clinical Trials

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Phase	Status	Purpose	Conditions	Count	Start Date	Why Stopped	100+ additional columns
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Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage Forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0408 mg/mL	ALOGPS
logP	1.23	ALOGPS
logP	1.15	Chemaxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.9	Chemaxon
pKa (Strongest Basic)	-1.2	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	5	Chemaxon
Polar Surface Area	123.32 Å²	Chemaxon
Rotatable Bond Count	9	Chemaxon
Refractivity	105.17 m³·mol^-1	Chemaxon
Polarizability	40.92 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9257
Blood Brain Barrier	+	0.7174
Caco-2 permeable	-	0.6893
P-glycoprotein substrate	Substrate	0.6278
P-glycoprotein inhibitor I	Non-inhibitor	0.8441
P-glycoprotein inhibitor II	Non-inhibitor	0.9049
Renal organic cation transporter	Non-inhibitor	0.9516
CYP450 2C9 substrate	Non-substrate	0.8618
CYP450 2D6 substrate	Non-substrate	0.7876
CYP450 3A4 substrate	Substrate	0.6018
CYP450 1A2 substrate	Non-inhibitor	0.7874
CYP450 2C9 inhibitor	Non-inhibitor	0.8053
CYP450 2D6 inhibitor	Non-inhibitor	0.8911
CYP450 2C19 inhibitor	Non-inhibitor	0.7102
CYP450 3A4 inhibitor	Non-inhibitor	0.8667
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9376
Ames test	Non AMES toxic	0.6111
Carcinogenicity	Non-carcinogens	0.8187
Biodegradation	Not ready biodegradable	0.9965
Rat acute toxicity	2.4741 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9946
hERG inhibition (predictor II)	Non-inhibitor	0.9059

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4r-1009000000-9eef80d04a76dc883e2b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0cdr-1029000000-0dac00264f9186112523
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0600-0291000000-67bff1829a55c7a006d0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a6s-2497000000-d2b852382c4ab4b0e72f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4l-0930000000-df4861893162c85cf6c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0btc-4940000000-2d3b0cb1a90c9e7b68fd
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	206.5249805	predicted	DarkChem Lite v0.1.0
[M-H]-	190.797	predicted	DeepCCS 1.0 (2019)
[M+H]+	207.7334805	predicted	DarkChem Lite v0.1.0
[M+H]+	193.19255	predicted	DeepCCS 1.0 (2019)
[M+Na]+	207.9051805	predicted	DarkChem Lite v0.1.0
[M+Na]+	199.10509	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Interstitial collagenase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Cleaves collagens of types I, II, and III at one site in the helical domain. Also cleaves collagens of types VII and X (PubMed:1645757, PubMed:2153297, PubMed:2557822). In case of HIV infection, interacts and cleaves the secreted viral Tat protein, leading to a decrease in neuronal Tat's mediated neurotoxicity (PubMed:16807369)
Specific Function: endopeptidase activity
Gene Name: MMP1
Uniprot ID: P03956
Uniprot Name: Interstitial collagenase
Molecular Weight: 54006.61 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details2. Matrix metalloproteinase-14

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Endopeptidase that degrades various components of the extracellular matrix such as collagen (PubMed:8015608). Essential for pericellular collagenolysis and modeling of skeletal and extraskeletal connective tissues during development (By similarity). Activates progelatinase A/MMP2, thereby acting as a positive regulator of cell growth and migration (PubMed:22065321, PubMed:8015608). Involved in the formation of the fibrovascular tissues in association with pro-MMP2 (PubMed:12714657, PubMed:22065321). May be involved in actin cytoskeleton reorganization by cleaving PTK7 (PubMed:20837484). Acts as a regulator of Notch signaling by mediating cleavage and inhibition of DLL1 (PubMed:21572390). Cleaves ADGRB1 to release vasculostatin-40 which inhibits angiogenesis (PubMed:22330140). Acts as a negative regulator of the GDF15-GFRAL aversive response by mediating cleavage and inactivation of GFRAL (PubMed:35177851)
Specific Function: endopeptidase activity
Gene Name: MMP14
Uniprot ID: P50281
Uniprot Name: Matrix metalloproteinase-14
Molecular Weight: 65893.445 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details3. Neutrophil collagenase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Can degrade fibrillar type I, II, and III collagens
Specific Function: endopeptidase activity
Gene Name: MMP8
Uniprot ID: P22894
Uniprot Name: Neutrophil collagenase
Molecular Weight: 53411.72 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details4. 72 kDa type IV collagenase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Ubiquitinous metalloproteinase that is involved in diverse functions such as remodeling of the vasculature, angiogenesis, tissue repair, tumor invasion, inflammation, and atherosclerotic plaque rupture. As well as degrading extracellular matrix proteins, can also act on several nonmatrix proteins such as big endothelial 1 and beta-type CGRP promoting vasoconstriction. Also cleaves KISS at a Gly-|-Leu bond. Appears to have a role in myocardial cell death pathways. Contributes to myocardial oxidative stress by regulating the activity of GSK3beta. Cleaves GSK3beta in vitro. Involved in the formation of the fibrovascular tissues in association with MMP14
Specific Function: endopeptidase activity
Gene Name: MMP2
Uniprot ID: P08253
Uniprot Name: 72 kDa type IV collagenase
Molecular Weight: 73881.695 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details5. Stromelysin-1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Metalloproteinase with a rather broad substrate specificity that can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates different molecules including growth factors, plasminogen or other matrix metalloproteinases such as MMP9 (PubMed:11029580, PubMed:1371271). Once released into the extracellular matrix (ECM), the inactive pro-enzyme is activated by the plasmin cascade signaling pathway (PubMed:2383557). Acts also intracellularly (PubMed:22265821). For example, in dopaminergic neurons, gets activated by the serine protease HTRA2 upon stress and plays a pivotal role in DA neuronal degeneration by mediating microglial activation and alpha-synuclein/SNCA cleavage (PubMed:21330369). In addition, plays a role in immune response and possesses antiviral activity against various viruses such as vesicular stomatitis virus, influenza A virus (H1N1) and human herpes virus 1 (PubMed:35940311). Mechanistically, translocates from the cytoplasm into the cell nucleus upon virus infection to influence NF-kappa-B activities (PubMed:35940311)
Specific Function: endopeptidase activity
Gene Name: MMP3
Uniprot ID: P08254
Uniprot Name: Stromelysin-1
Molecular Weight: 53976.84 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details6. Matrix metalloproteinase-9

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Matrix metalloproteinase that plays an essential role in local proteolysis of the extracellular matrix and in leukocyte migration (PubMed:12879005, PubMed:1480034, PubMed:2551898). Could play a role in bone osteoclastic resorption (By similarity). Cleaves KiSS1 at a Gly-|-Leu bond (PubMed:12879005). Cleaves NINJ1 to generate the Secreted ninjurin-1 form (PubMed:32883094). Cleaves type IV and type V collagen into large C-terminal three quarter fragments and shorter N-terminal one quarter fragments (PubMed:1480034). Degrades fibronectin but not laminin or Pz-peptide
Specific Function: collagen binding
Gene Name: MMP9
Uniprot ID: P14780
Uniprot Name: Matrix metalloproteinase-9
Molecular Weight: 78457.51 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details7. Macrophage metalloelastase

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: May be involved in tissue injury and remodeling. Has significant elastolytic activity. Can accept large and small amino acids at the P1' site, but has a preference for leucine. Aromatic or hydrophobic residues are preferred at the P1 site, with small hydrophobic residues (preferably alanine) occupying P3
Specific Function: calcium ion binding
Gene Name: MMP12
Uniprot ID: P39900
Uniprot Name: Macrophage metalloelastase
Molecular Weight: 54001.175 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details8. Collagenase 3

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Plays a role in the degradation of extracellular matrix proteins including fibrillar collagen, fibronectin, TNC and ACAN. Cleaves triple helical collagens, including type I, type II and type III collagen, but has the highest activity with soluble type II collagen. Can also degrade collagen type IV, type XIV and type X. May also function by activating or degrading key regulatory proteins, such as TGFB1 and CCN2. Plays a role in wound healing, tissue remodeling, cartilage degradation, bone development, bone mineralization and ossification. Required for normal embryonic bone development and ossification. Plays a role in the healing of bone fractures via endochondral ossification. Plays a role in wound healing, probably by a mechanism that involves proteolytic activation of TGFB1 and degradation of CCN2. Plays a role in keratinocyte migration during wound healing. May play a role in cell migration and in tumor cell invasion
Specific Function: calcium ion binding
Gene Name: MMP13
Uniprot ID: P45452
Uniprot Name: Collagenase 3
Molecular Weight: 53819.32 Da

References

Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details9. Lethal factor

Kind: Protein
Organism: Bacillus anthracis
Pharmacological action: Yes
Actions: Inhibitor

General Function: Lethal factor (LF), which constitutes one of the three proteins composing the anthrax toxin, is able to trigger rapid cell death in macrophages (PubMed:10475971, PubMed:11104681, PubMed:3711080, PubMed:8380282, PubMed:9563949, PubMed:9703991). Acts as a protease that cleaves the N-terminal of most dual specificity mitogen-activated protein kinase kinases (MAPKKs or MAP2Ks) (except for MAP2K5): cleavage invariably occurs within the N-terminal proline-rich region preceding the kinase domain, thus disrupting a sequence involved in directing specific protein-protein interactions necessary for the assembly of signaling complexes (PubMed:10475971, PubMed:11104681, PubMed:14718925, PubMed:9563949, PubMed:9703991). Also cleaves mouse Nlrp1b: host Nlrp1b cleavage promotes ubiquitination and degradation of the N-terminal part of Nlrp1b by the proteasome, thereby releasing the cleaved C-terminal part of Nlrp1b, which polymerizes and forms the Nlrp1b inflammasome followed by host cell pyroptosis (PubMed:10338520, PubMed:19651869, PubMed:30872531, PubMed:31268597). Able to cleave mouse Nlrp1b alleles 1 and 5, while it is not able to cleave Nlrp1b alleles 2, 3 and 4 (PubMed:16429160, PubMed:19651869). In contrast, does not cleave NLRP1 human ortholog (PubMed:19651869). LF is not toxic by itself and only acts as a lethal factor when associated with protective antigen (PA) to form the lethal toxin (LeTx): PA is required for LF translocation into the host cytosol (PubMed:10475971, PubMed:11104681, PubMed:9563949, PubMed:9703991).
Specific Function: metalloendopeptidase activity
Gene Name: lef
Uniprot ID: P15917
Uniprot Name: Lethal factor
Molecular Weight: 93769.58 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Details10. Disintegrin and metalloproteinase domain-containing protein 28

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: May play a role in the adhesive and proteolytic events that occur during lymphocyte emigration or may function in ectodomain shedding of lymphocyte surface target proteins, such as FASL and CD40L. May be involved in sperm maturation
Specific Function: immunoglobulin receptor binding
Gene Name: ADAM28
Uniprot ID: Q9UKQ2
Uniprot Name: Disintegrin and metalloproteinase domain-containing protein 28
Molecular Weight: 87147.04 Da

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Details11. Aggrecan core protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: This proteoglycan is a major component of extracellular matrix of cartilagenous tissues. A major function of this protein is to resist compression in cartilage. It binds avidly to hyaluronic acid via an N-terminal globular region
Specific Function: carbohydrate binding
Gene Name: ACAN
Uniprot ID: P16112
Uniprot Name: Aggrecan core protein
Molecular Weight: 261326.125 Da

References

Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:21

Ilomastat

Identification

Structure for Ilomastat (DB02255)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Clinical Trial & Rare Diseases Add-on Data Package

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

References

References

References

References

References

References

References