Ilomastat
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MedKoo CAT#: 406491

CAS#: 142880-36-2

Description: 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

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Ilomastat
CAS# 142880-36-2

Theoretical Analysis

MedKoo Cat#: 406491
Name: Ilomastat
CAS#: 142880-36-2
Chemical Formula: C20H28N4O4
Exact Mass: 388.21106
Molecular Weight: 388.46072
Elemental Analysis: C, 61.84; H, 7.27; N, 14.42; O, 16.47

Price and Availability

Size Price Availability Quantity
10.0mg USD 150.0 Same day
25.0mg USD 250.0 Same day
50.0mg USD 450.0 Same day
100.0mg USD 750.0 Same day
200.0mg USD 1250.0 Same day
500.0mg USD 1950.0 Same day
1.0g USD 3250.0 Same day
2.0g USD 5850.0 2 weeks
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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

Preparing Stock Solutions

The following data is based on the product molecular weight 388.46072 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

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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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