TMI-1 | CAS#287403-39-8

TMI-1
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 526473

CAS#: 287403-39-8

Description: TMI-1 is a novel orally active inhibitor of ADAM17 (TACE) and MMP, inducing tumor apoptosis in a breast cancer.

Chemical Structure

TMI-1

CAS# 287403-39-8

Instruction

Theoretical Analysis

MedKoo Cat#: 526473
Name: TMI-1
CAS#: 287403-39-8
Chemical Formula: C17H22N2O5S2
Exact Mass: 398.10
Molecular Weight: 398.490
Elemental Analysis: C, 51.24; H, 5.56; N, 7.03; O, 20.07; S, 16.09

Price and Availability

Size	Price	Availability
5mg	USD 280	2 Weeks
25mg	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: TMI-1

IUPAC/Chemical Name: (3S)-4-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-3-thiomorpholinecarboxamide

InChi Key: CVZIHNYAZLXRRS-HNNXBMFYSA-N

InChi Code: InChI=1S/C17H22N2O5S2/c1-4-5-11-24-13-6-8-14(9-7-13)26(22,23)19-10-12-25-17(2,3)15(19)16(20)18-21/h6-9,15,21H,10-12H2,1-3H3,(H,18,20)/t15-/m0/s1

SMILES Code: O=C([C@@H]1N(S(=O)(C2=CC=C(OCC#CC)C=C2)=O)CCSC1(C)C)NO

Appearance: 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

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:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 398.49 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.

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:
In vivo protocol:

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1: Vigouroux F, Rabarin F, Jeudy J, Bigorre N, Saint Cast Y, Pechmajou L, Raimbeau G. Peritrapezial osteoarthritis: Inter- and intraobserver reliability of the Allieu classification. Hand Surg Rehabil. 2017 Oct;36(5):363-367. doi: 10.1016/j.hansur.2017.06.008. Epub 2017 Aug 16. PubMed PMID: 28822670.

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3: Beck Gooz M, Maldonado EN, Dang Y, Amria MY, Higashiyama S, Abboud HE, Lemasters JJ, Bell PD. ADAM17 promotes proliferation of collecting duct kidney epithelial cells through ERK activation and increased glycolysis in polycystic kidney disease. Am J Physiol Renal Physiol. 2014 Sep 1;307(5):F551-9. doi: 10.1152/ajprenal.00218.2014. Epub 2014 Jun 4. PubMed PMID: 24899059; PubMed Central PMCID: PMC4154111.

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5: Mezil L, Berruyer-Pouyet C, Cabaud O, Josselin E, Combes S, Brunel JM, Viens P, Collette Y, Birnbaum D, Lopez M. Tumor selective cytotoxic action of a thiomorpholin hydroxamate inhibitor (TMI-1) in breast cancer. PLoS One. 2012;7(9):e43409. doi: 10.1371/journal.pone.0043409. Epub 2012 Sep 18. PubMed PMID: 23028451; PubMed Central PMCID: PMC3445597.

6: Lerman Y, Werber MM, Fine I, Kemelman P. Preliminary clinical evaluation of a noninvasive device for the measurement of coagulability in the elderly. J Blood Med. 2011;2:113-8. doi: 10.2147/JBM.S13544. Epub 2011 Aug 18. PubMed PMID: 22287870; PubMed Central PMCID: PMC3262344.

7: Shu C, Zhou H, Afsharvand M, Duan L, Zhang H, Noveck R, Raible D. Pharmacokinetic-pharmacodynamic modeling of apratastat: a population-based approach. J Clin Pharmacol. 2011 Apr;51(4):472-81. doi: 10.1177/0091270010372389. Epub 2010 Nov 8. PubMed PMID: 21059888.

8: Moss ML, Rasmussen FH, Nudelman R, Dempsey PJ, Williams J. Fluorescent substrates useful as high-throughput screening tools for ADAM9. Comb Chem High Throughput Screen. 2010 May;13(4):358-65. PubMed PMID: 20015014.

9: Moss ML, Rasmussen FH. Fluorescent substrates for the proteinases ADAM17, ADAM10, ADAM8, and ADAM12 useful for high-throughput inhibitor screening. Anal Biochem. 2007 Jul 15;366(2):144-8. Epub 2007 May 3. PubMed PMID: 17548045.

10: Thabet MM, Huizinga TW. Drug evaluation: apratastat, a novel TACE/MMP inhibitor for rheumatoid arthritis. Curr Opin Investig Drugs. 2006 Nov;7(11):1014-9. PubMed PMID: 17117591.

11: Toth JL, Trzupek JD, Flores LV, Kiakos K, Hartley JA, Pennington WT, Lee M. A novel achiral seco-amino-cyclopropylindoline (CI) analog of CC-1065 and the duocarmycins: design, synthesis and biological studies. Med Chem. 2005 Jan;1(1):13-9. PubMed PMID: 16789881.

12: Bergmeier W, Piffath CL, Cheng G, Dole VS, Zhang Y, von Andrian UH, Wagner DD. Tumor necrosis factor-alpha-converting enzyme (ADAM17) mediates GPIbalpha shedding from platelets in vitro and in vivo. Circ Res. 2004 Oct 1;95(7):677-83. Epub 2004 Sep 2. PubMed PMID: 15345652.

13: Zhang Y, Xu J, Levin J, Hegen M, Li G, Robertshaw H, Brennan F, Cummons T, Clarke D, Vansell N, Nickerson-Nutter C, Barone D, Mohler K, Black R, Skotnicki J, Gibbons J, Feldmann M, Frost P, Larsen G, Lin LL. Identification and characterization of 4-[[4-(2-butynyloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-(3S)thiomorpholinecar boxamide (TMI-1), a novel dual tumor necrosis factor-alpha-converting enzyme/matrix metalloprotease inhibitor for the treatment of rheumatoid arthritis. J Pharmacol Exp Ther. 2004 Apr;309(1):348-55. Epub 2004 Jan 12. PubMed PMID: 14718605.

14: Kuroyanagi T, Kura K. The in vitro development of immunoglobulin producing cells from the human bone marrow null lymphocyte. Tohoku J Exp Med. 1981 Mar;133(3):257-66. PubMed PMID: 7198307.

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