NAV

Ilomastat

Identification

Generic Name
Ilomastat
DrugBank Accession Number
DB02255
Background

Ilomastat is a broad-spectrum matrix metalloproteinase inhibitor.

Type
Small Molecule
Groups
Experimental
Structure
3D
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
TargetActionsOrganism
UDisintegrin and metalloproteinase domain-containing protein 28Not AvailableHumans
UAggrecan core proteinNot AvailableHumans
ULethal factorNot AvailableBacillus anthracis
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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

Products

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International/Other Brands
Galardin

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Tryptamines and derivatives / Alpha amino acid amides / 3-alkylindoles / Substituted pyrroles / N-acyl amines / Benzenoids / Heteroaromatic compounds / Secondary carboxylic acid amides / Hydroxamic acids / Azacyclic compounds
show 5 more
Substituents
3-alkylindole / Alpha-amino acid amide / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Fatty acyl / Fatty amide / Heteroaromatic compound
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

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
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

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.0408 mg/mLALOGPS
logP1.23ALOGPS
logP1.15Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)8.9Chemaxon
pKa (Strongest Basic)-1.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area123.32 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity105.17 m3·mol-1Chemaxon
Polarizability40.92 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9257
Blood Brain Barrier+0.7174
Caco-2 permeable-0.6893
P-glycoprotein substrateSubstrate0.6278
P-glycoprotein inhibitor INon-inhibitor0.8441
P-glycoprotein inhibitor IINon-inhibitor0.9049
Renal organic cation transporterNon-inhibitor0.9516
CYP450 2C9 substrateNon-substrate0.8618
CYP450 2D6 substrateNon-substrate0.7876
CYP450 3A4 substrateSubstrate0.6018
CYP450 1A2 substrateNon-inhibitor0.7874
CYP450 2C9 inhibitorNon-inhibitor0.8053
CYP450 2D6 inhibitorNon-inhibitor0.8911
CYP450 2C19 inhibitorNon-inhibitor0.7102
CYP450 3A4 inhibitorNon-inhibitor0.8667
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9376
Ames testNon AMES toxic0.6111
CarcinogenicityNon-carcinogens0.8187
BiodegradationNot ready biodegradable0.9965
Rat acute toxicity2.4741 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9946
hERG inhibition (predictor II)Non-inhibitor0.9059
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-1009000000-9eef80d04a76dc883e2b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0cdr-1029000000-0dac00264f9186112523
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0600-0291000000-67bff1829a55c7a006d0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6s-2497000000-d2b852382c4ab4b0e72f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-0930000000-df4861893162c85cf6c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0btc-4940000000-2d3b0cb1a90c9e7b68fd
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[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. Disintegrin and metalloproteinase domain-containing protein 28
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific 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. ...
Gene Name
ADAM28
Uniprot ID
Q9UKQ2
Uniprot Name
Disintegrin and metalloproteinase domain-containing protein 28
Molecular Weight
87147.04 Da
References
  1. 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]
Details2. Aggrecan core protein
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Metal ion binding
Specific 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 v...
Gene Name
ACAN
Uniprot ID
P16112
Uniprot Name
Aggrecan core protein
Molecular Weight
250190.95 Da
References
  1. 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]
Details3. Lethal factor
Kind
Protein
Organism
Bacillus anthracis
Pharmacological action
Unknown
General Function
Metallopeptidase activity
Specific Function
One of the three proteins composing the anthrax toxin, the agent which infects many mammalian species and that may cause death. LF is the lethal factor that, when associated with PA, causes death. ...
Gene Name
lef
Uniprot ID
P15917
Uniprot Name
Lethal factor
Molecular Weight
93769.58 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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 September 30, 2023 19:51