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MedKoo Cat#: 530017 | Name: Apratastat
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Description:

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

Apratastat, also known as TMI-005 and XMT-1191, is a matrix metalloproteinase/tumour necrosis factor-α convertase inhibitor.

Chemical Structure

Apratastat
Apratastat
CAS#287405-51-0

Theoretical Analysis

MedKoo Cat#: 530017

Name: Apratastat

CAS#: 287405-51-0

Chemical Formula: C17H22N2O6S2

Exact Mass: 414.0900

Molecular Weight: 414.49

Elemental Analysis: C, 49.26; H, 5.35; N, 6.76; O, 23.16; S, 15.47

Price and Availability

Size Price Availability Quantity
5mg USD 400.00 2 Weeks
10mg USD 750.00 2 Weeks
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Related CAS #
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Synonym
TMI-005; TMI005; TMI 005; XMT-1191; XMT 1191; XMT1191. Apratastat.
IUPAC/Chemical Name
(3S)-N-Hydroxy-4-((4-((4-hydroxybut-2-ynyl)oxy)phenyl)sulfonyl)-2,2-dimethylthiomorpholine-3-carboxamide
InChi Key
MAVDNGWEBZTACC-HNNXBMFYSA-N
InChi Code
InChI=1S/C17H22N2O6S2/c1-17(2)15(16(21)18-22)19(9-12-26-17)27(23,24)14-7-5-13(6-8-14)25-11-4-3-10-20/h5-8,15,20,22H,9-12H2,1-2H3,(H,18,21)/t15-/m0/s1
SMILES Code
O=C([C@@H]1N(S(=O)(C2=CC=C(OCC#CCO)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

Preparing Stock Solutions

The following data is based on the product molecular weight 414.49 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.

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
1: 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. PMID: 21059888. 2: Jocher G, Grass V, Tschirner SK, Riepler L, Breimann S, Kaya T, Oelsner M, Hamad MS, Hofmann LI, Blobel CP, Schmidt-Weber CB, Gokce O, Jakwerth CA, Trimpert J, Kimpel J, Pichlmair A, Lichtenthaler SF. ADAM10 and ADAM17 promote SARS-CoV-2 cell entry and spike protein-mediated lung cell fusion. EMBO Rep. 2022 Jun 7;23(6):e54305. doi: 10.15252/embr.202154305. Epub 2022 May 8. PMID: 35527514; PMCID: PMC9171409. 3: 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. PMID: 17117591. 4: Lartey NL, Valle-Reyes S, Vargas-Robles H, Jiménez-Camacho KE, Guerrero- Fonseca IM, Castellanos-Martínez R, Montoya-García A, García-Cordero J, Cedillo- Barrón L, Nava P, Filisola-Villaseñor JG, Roa-Velázquez D, Zavala-Vargas DI, Morales-Ríos E, Salinas-Lara C, Vadillo E, Schnoor M. ADAM17/MMP inhibition prevents neutrophilia and lung injury in a mouse model of COVID-19. J Leukoc Biol. 2022 Jun;111(6):1147-1158. doi: 10.1002/JLB.3COVA0421-195RR. Epub 2021 Nov 26. PMID: 34826347; PMCID: PMC9015574. 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. PMID: 23028451; PMCID: PMC3445597. 6: 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. doi: 10.1016/j.ab.2007.04.043. Epub 2007 May 3. PMID: 17548045. 7: 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. PMID: 24899059; PMCID: PMC4154111. 8: 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. doi: 10.1161/01.RES.0000143899.73453.11. Epub 2004 Sep 2. PMID: 15345652. 9: 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)thiomorpholinecarboxamide (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. doi: 10.1124/jpet.103.059675. Epub 2004 Jan 12. PMID: 14718605.