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MedKoo Cat#: 406491 | Name: Ilomastat
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Ilomastat, also known as GM6001 and galardin, is a broad-spectrum matrix metalloproteinase inhibitor with potential anticancer activity. GM6001 is a member of the hydroxamic acid class of reversible metallopeptidase inhibitors. The anionic state of the hydroxamic acid group forms a bidentate complex with the active site zinc. Examples of enzymes that ilomastat inhibit include thermolysin, peptide deformylase, and anthrax lethal factor endopeptidase (LF) produced by the bacterium Bacillus anthracis.

Chemical Structure

Ilomastat
Ilomastat
CAS#142880-36-2

Theoretical Analysis

MedKoo Cat#: 406491

Name: Ilomastat

CAS#: 142880-36-2

Chemical Formula: C20H28N4O4

Exact Mass: 388.2111

Molecular Weight: 388.46

Elemental Analysis: C, 61.84; H, 7.27; N, 14.42; O, 16.47

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,250.00 Ready to ship
500mg USD 2,850.00 Ready to ship
1g USD 3,850.00 Ready to ship
2g USD 6,450.00 Ready to ship
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Related CAS #
No Data
Synonym
GM6001; GM-6001; GM 6001; Ilomastat; galardin.
IUPAC/Chemical Name
(R)-N1-((S)-3-(1H-indol-3-yl)-1-(methylamino)-1-oxopropan-2-yl)-N4-hydroxy-2-isobutylsuccinamide
InChi Key
NITYDPDXAAFEIT-DYVFJYSZSA-N
InChi Code
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
SMILES Code
O=C(NC)[C@@H](NC([C@@H](CC(NO)=O)CC(C)C)=O)CC1=CNC2=CC=CC=C21
Appearance
Beige to brown solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
        
Biological target:
Ilomastat (GM6001) is a potent and broad spectrum matrix metalloprotease (MMP) inhibitor, inhibits MMPs (IC50s, 1.5 nM for MMP-1; 1.1 nM for MMP-2; 1.9 nM for MMP-3; 0.5 nM for MMP-9), with a Ki of 0.4 nM for human skin fibroblast collagenase (MMP-1).
In vitro activity:
To further assess the cytoprotective effect of ilomastat, primary cardiomyocytes isolated from neonatal rats were subjected to 240min simulated ischemia followed by 120min simulated reperfusion in the presence of ilomastat (5nM-5μM). Ilomastat at 500nM and 5μM significantly increased cell viability when compared to vehicle treated group. To assess the in situ MMP-2 inhibitory effect of ilomastat, in separate experiments in situ zymography was performed in cardiomyocytes. The cytoprotective concentration of ilomastat (500nM) showed a moderate (approximately 25%) inhibition of intracellular MMP-2 in ischemic/reperfused cardiomyocytes. In these cells, MMP-2 immunostaining showed a 90% colocalization with the in situ gelatinolytic activity Reference: Pharmacol Res. 2014 Feb;80:36-42. https://linkinghub.elsevier.com/retrieve/pii/S1043-6618(13)00280-6
In vivo activity:
All mice treated with different dosed of ilomastat showed faster recovery, especially at day 20, for peripheral blood cell count compared to the irradiation alone group (Figure 1A). In particular, ilomastat accelerated recovery of the white blood cell WBC count in the peripheral blood of irradiated mice. The red blood cell (RBC) count was significantly recovered at day 20 after TBI when the mice were administered 10 mg/kg ilomastat 2 h prior to TBI. In contrast, the RBC count decreased to a minimum at day 20, and then recovered at day 30 in the mice that received irradiation without ilomastat (Figure 1B). Similarly, the hemoglobin levels in the irradiated mice without Ilomastat pretreatment decreased at days 5 and 10, and reached a minimum at day 20. In mice pretreated with ilomastat, there was rapid recovery of hemoglobin (Figure 1C). The platelet levels in the irradiation alone group reached a minimum at day 10 and failed to fully recover at day 20 post-TBI. Ilomastat pretreatment significantly recovered the platelet levels in the irradiated mice at days 10 and 20 (Figure 1D). Pretreatment with 10 mg/kg ilomastat significantly increased lymphocyte count at day 20 post-TBI, compared with the irradiation alone group (P < 0.001, Figure 1E). Pretreatment with 10 and 50 mg/kg ilomastat significantly increased the number of neutrophils at days 1-20 post-TBI (P < 0.001, Figure 1F). The RBC and hemoglobin levels recovered faster with 10 mg/kg ilomastat compared with other doses. Therefore, to reduce drug consumption and any burden on the mice, we primarily used 10 mg/kg for subsequent protection/mitigation experiments. Reference: Biomed Environ Sci. 2018 Jun;31(6):467-472. https://doi.org/10.3967/bes2018.062
Solvent mg/mL mM
Solubility
DMSO 47.0 120.99
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 388.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Bencsik P, Pálóczi J, Kocsis GF, Pipis J, Belecz I, Varga ZV, Csonka C, Görbe A, Csont T, Ferdinandy P. Moderate inhibition of myocardial matrix metalloproteinase-2 by ilomastat is cardioprotective. Pharmacol Res. 2014 Feb;80:36-42. doi: 10.1016/j.phrs.2013.12.007. Epub 2013 Dec 28. PMID: 24380772.
In vivo protocol:
1. Li XM, Tan Y, Huang CQ, Xu MC, Li Q, Pan D, Zhao BQ, Hu BR. MMP Inhibitor Ilomastat Improves Survival of Mice Exposed to γ-Irradiation. Biomed Environ Sci. 2018 Jun;31(6):467-472. doi: 10.3967/bes2018.062. PMID: 30025561. 2. Bencsik P, Pálóczi J, Kocsis GF, Pipis J, Belecz I, Varga ZV, Csonka C, Görbe A, Csont T, Ferdinandy P. Moderate inhibition of myocardial matrix metalloproteinase-2 by ilomastat is cardioprotective. Pharmacol Res. 2014 Feb;80:36-42. doi: 10.1016/j.phrs.2013.12.007. Epub 2013 Dec 28. PMID: 24380772.
1: Bencsik P, Pálóczi J, Kocsis GF, Pipis J, Belecz I, Varga ZV, Csonka C, Görbe A, Csont T, Ferdinandy P. Moderate inhibition of myocardial matrix metalloproteinase-2 by ilomastat is cardioprotective. Pharmacol Res. 2014 Feb;80:36-42. doi: 10.1016/j.phrs.2013.12.007. Epub 2013 Dec 28. PubMed PMID: 24380772. 2: Parkinson G, Gaisford S, Ru Q, Lockwood A, Khalili A, Sheridan R, Khaw PT, Brocchini S, Fadda HM. Characterisation of ilomastat for prolonged ocular drug release. AAPS PharmSciTech. 2012 Dec;13(4):1063-72. doi: 10.1208/s12249-012-9832-1. Epub 2012 Aug 18. PubMed PMID: 22903888; PubMed Central PMCID: PMC3513442. 3: Senhao L, Dongqin Q. Preparation and in vitro evaluation of an ilomastat microemulsion gel by a self-microemulsifying system. Pharmazie. 2012 Feb;67(2):156-60. PubMed PMID: 22512086. 4: Yeh DY, Lin HI, Feng NH, Chen CF, Wang D, Wang NT. Matrix metalloprotease expressions in both reperfusion lung injury and oleic acid lung injury models and the protective effects of ilomastat. Transplant Proc. 2009 Jun;41(5):1508-11. doi: 10.1016/j.transproceed.2009.02.076. PubMed PMID: 19545667. 5: Wang YD, Wang W. Protective effect of ilomastat on trinitrobenzenesulfonic acid-induced ulcerative colitis in rats. World J Gastroenterol. 2008 Oct 7;14(37):5683-8. PubMed PMID: 18837084; PubMed Central PMCID: PMC2748202. 6: Ledour G, Moroy G, Rouffet M, Bourguet E, Guillaume D, Decarme M, Elmourabit H, Augé F, Alix AJ, Laronze JY, Bellon G, Hornebeck W, Sapi J. Introduction of the 4-(4-bromophenyl)benzenesulfonyl group to hydrazide analogs of Ilomastat leads to potent gelatinase B (MMP-9) inhibitors with improved selectivity. Bioorg Med Chem. 2008 Sep 15;16(18):8745-59. doi: 10.1016/j.bmc.2008.07.041. Epub 2008 Jul 20. PubMed PMID: 18782669. 7: Moroy G, Denhez C, El Mourabit H, Toribio A, Dassonville A, Decarme M, Renault JH, Mirand C, Bellon G, Sapi J, Alix AJ, Hornebeck W, Bourguet E. Simultaneous presence of unsaturation and long alkyl chain at P'1 of Ilomastat confers selectivity for gelatinase A (MMP-2) over gelatinase B (MMP-9) inhibition as shown by molecular modelling studies. Bioorg Med Chem. 2007 Jul 15;15(14):4753-66. Epub 2007 May 6. PubMed PMID: 17512742. 8: Kocer SS, Walker SG, Zerler B, Golub LM, Simon SR. Metalloproteinase inhibitors, nonantimicrobial chemically modified tetracyclines, and ilomastat block Bacillus anthracis lethal factor activity in viable cells. Infect Immun. 2005 Nov;73(11):7548-57. PubMed PMID: 16239558; PubMed Central PMCID: PMC1273843. 9: Wong TT, Mead AL, Khaw PT. Prolonged antiscarring effects of ilomastat and MMC after experimental glaucoma filtration surgery. Invest Ophthalmol Vis Sci. 2005 Jun;46(6):2018-22. PubMed PMID: 15914618. 10: Antonelli PJ, Schultz GS, Sundin DJ, Pemberton PA, Barr PJ. Protease inhibitors alpha1-antitrypsin and ilomastat are not ototoxic in the chinchilla. Laryngoscope. 2003 Oct;113(10):1764-9. PubMed PMID: 14520103. 11: Antonelli PJ, Schultz GS, Kim KM, Cantwell JS, Sundin DJ, Pemberton PA, Barr PJ. Alpha 1-antitrypsin and ilomastat inhibit inflammatory proteases present in human middle ear effusions. Laryngoscope. 2003 Aug;113(8):1347-51. PubMed PMID: 12897557.

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