Ilomastat

Base Information

• Chemical Name: Ilomastat
• CAS No.: 142880-36-2
• Molecular Formula: C20H28 N4 O4
• Molecular Weight: 388.467
• Hs Code.: 29339900
• NSC Number: 727632
• UNII: I0403ML141
• DSSTox Substance ID: DTXSID0046353
• Nikkaji Number: J601.478J
• Wikipedia: Ilomastat
• Wikidata: Q5513695
• NCI Thesaurus Code: C96286
• Pharos Ligand ID: SWC2P7KY8XKG
• Metabolomics Workbench ID: 146850
• ChEMBL ID: CHEMBL19611
• Mol file: 142880-36-2.mol

Synonyms:Ilomastat;142880-36-2;Galardin;GM6001;GM 6001;Illomastat;Ilomastat [USAN];CS 610;GM-6001;Galardin MPI;Ilomastat (GM6001, Galardin);Ilomastat (USAN/INN);Ilomastat [USAN:INN];(R)-N1-((S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl)-N4-hydroxy-2-isobutylsuccinamide;CHEMBL19611;DTXSID0046353;UNII-I0403ML141;CS-610;(R)-N(sup 1)-Hydroxy-N-((S)-2-indol-3-yl-1-(methylcarbamoyl)ethyl)-2-isobutylsuccinamide;I0403ML141;(S-(R*,S*))-N(sup 4)-Hydroxy-N(sup 1)-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylopropyl)butanediamide;NCGC00163450-02;3-(N-HYDROXYCARBOXAMIDO)-2-ISOBUTYLPROPANOYL-TRP-METHYLAMIDE;(2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide;Butanediamide, N4-hydroxy-N1-((1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)-, (2R)-;Butanediamide, N4-hydroxy-N1-(1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl)-2-(2-methylpropyl)-, (S-(R*,S*))-;4pkw;GM6;MFCD03453614;ILOMASTAT [INN];ILOMASTAT [INCI];D05WSY;D0K6UI;D0T9HG;(R)-N4-Hydroxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide;CBiol_001883;SCHEMBL35303;BSPBio_001079;KBioGR_000419;KBioSS_000419;GTPL7409;DTXCID8026353;BCBcMAP01_000057;KBio2_000419;KBio2_002987;KBio2_005555;KBio3_000797;KBio3_000798;EX-A765;CHEBI:137236;BDBM234334;Bio1_000169;Bio1_000658;Bio1_001147;Bio2_000370;Bio2_000850;HMS1362E21;HMS1792E21;HMS1990E21;HMS3403E21;Tox21_112055;BDBM50062351;NSC727632;s7157;AKOS016355429;CCG-207857;CS-1701;DB02255;NSC-727632;IDI1_002125;SMP2_000212;NCGC00163450-01;NCGC00163450-03;NCGC00163450-04;AS-56152;HY-15768;LS-186959;LS-187605;CAS-142880-36-2;SW218170-2;D03793;J-007712;BRD-K51662849-001-02-1;GM 6001 - CAS 142880-36-2;(R)-N*4*-Hydroxy-N*1*-[2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide;(2R)-N'-hydroxy-N-[(2S)-3-(1H-indol-3-yl)-1-methylamino-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide;(2R)-N(4)-hydroxy-N(1)-[(2S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl]-2-(2-methylpropyl)butanediamide;(2R)-N4-Hydroxy-N1-[(1S)-1-(1H-indol-3-ylmethyl)-2-(methylamino)-2-oxoethyl]-2-(2-methylpropyl)butanediamide;(R)-N*4*-Hydroxy-N*1*-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide;(R)-N1-((S)-3-(1H-Indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl)-N4-hydroxy-2-isobutyl succinamide

Chemical Property of Ilomastat

Chemical Property:

• Boiling Point: °Cat760mmHg
• PKA: 9.16±0.20(Predicted)
• Flash Point: °C
• PSA: 123.32000
• Density: 1.228g/cm³
• LogP: 2.67170
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Soluble in DMSO, and 100% ethanol.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 388.21105539
• Heavy Atom Count: 28
• Complexity: 554

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ilomastat ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CC(CC(=O)NO)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)NC
• Isomeric SMILES: CC(C)C[C@H](CC(=O)NO)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)NC
• Description: Ilomastat (142880-36-2) is a potent pan-specific inhibitor of matrix metalloproteinases (MMPs).1 Ki values have been reported for the following human MMPs: MMP-1, 0.4nM; MMP-2, 0.5nM; MMP-3, 27nM; MMP-7, 3.7nM; MMP-8, 0.1nM; MMP-9, 0.2nM; MMP-12, 3.6nM; MMP-14, 13.4nM; MMP-26, 0.36nM.2-4 Also inhibits MMP-10, MMP-13, MMP-15, MMP-17, MMP-20, MMP-21, TACE and ADAM19.
• Uses: GM 6001 is a potent, reversible broad spectrum inhibitor of zinc-containing proteases, including matrix metalloproteinases (MMPs). It inhibits zinc-containing thermolysin and elastase from P. aeruginosa, both with Ki values of 20 nM. GM 6001 inhibits MMP-1, -2, -7, -8, -9, -12, -13, -14, -16, and -26 with Ki or IC50 values between 0.1 and 10 nM. It inhibits disintegrin and metalloproteinase domain-containing (ADAM) proteins ADAM9, ADAM10, ADAM12, and ADAM17 at nanomolar concentrations. It less potently inhibits lethal factor from B. anthracis anthrax lethal toxin (Ki = 2.74 μM). GM 6001 also impairs the growth of the human pathogen Chlamydia by inhibiting peptide deformylase, which contains iron rather than zinc (IC50 = 38 nM). Ilomastat is a metalloprotease inhibitor.

Technology Process of Ilomastat

There total 13 articles about Ilomastat which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(R)-N4-Benzyloxy-N1-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide (171347-80-1) → galardin (142880-36-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jm970404a

Reference yield:

(S)-2-amino-3-(1H-indol-3-yl)-N-methylpropanamide (53708-63-7) → galardin (142880-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-ethyl-3<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / Ambient temperature

2: H₂ / 10 percent Pd/C / methanol

With hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm970404a

Reference yield:

4--2(R)-isobutylsuccinic acid → galardin (142880-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-ethyl-3<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / Ambient temperature

2: H₂ / 10 percent Pd/C / methanol

With hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm970404a

upstream raw materials:

(R)-3-[(S)-2-(1H-Indol-3-yl)-1-methylcarbamoyl-ethylcarbamoyl]-5-methyl-hexanoic acid methyl ester

(R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide

(S)-2-amino-3-(1H-indol-3-yl)-N-methylpropanamide

2-methyl-2-propen-1-yl succinic anhydride

Downstream raw materials:

(R)-N⁴-Benzyloxy-N¹-[(S)-2-(1H-indol-3-yl)-1-methylcarbamoyl-ethyl]-2-isobutyl-succinamide

Refernces

• 1、 Levy, Daniel E.,Lapierre, France,Liang, Weisheng,Ye, Wenqing,Lange, Christopher W.,Li, Xiaoyuan,Grobelny, Damian,Casabonne, Marie,Tyrrell, David,Holme, Kevin,Nadzan, Alex,Galardy, Richard E.. "Matrix metalloproteinase inhibitors: A structure-activity study". . p. 199 - 223. Retrieved 2007/10/03.