An inhibitor of ADAM17 and MMPs
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TMI-005

Item No. 29016

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S)-N-hydroxy-4-[[4-[(4-hydroxy-2-butyn-1-yl)oxy]phenyl]sulfonyl]-2,2-dimethyl-3-thiomorpholinecarboxamide
CAS Number
287405-51-0
Synonyms
  • Apratastat
Molecular Formula
C17H22N2O6S2
Formula Weight
414.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 25 mg/mlDMSO:PBS (pH 7.2) (1:40): 0.02 mg/mlEthanol: 10 mg/ml
λmax
242 nm
SMILES
O=S(C1=CC=C(OCC#CCO)C=C1)(N2CCSC(C)(C)[C@@H]2C(NO)=O)=O
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
InChi Key
MAVDNGWEBZTACC-HNNXBMFYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

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    10 mg

    $376

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    Cayman Chemical
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    Product Description

    TMI-005 is an inhibitor of disintegrin and metalloproteinase domain-containing protein 17/TNF-α converting enzyme (ADAM17/TACE), matrix metalloproteinase-1 (MMP-1), and MMP-13 (IC50s = 20, 33, and 8.1 nM, respectively).1 It inhibits LPS-induced TNF-α release in isolated human whole blood (IC50 = 144 ng/ml).2 TMI-005 (25 μM) reduces basal and ionizing radiation-induced secretion of the ADAM17/TACE substrates ALCAM and amphiregulin from A549 and NCI H125 cells.3 It inhibits proliferation of A549 cells when used at concentrations of 25 and 50 μM and sensitizes A549 and NCI H125 cells to ionizing radiation at 25 μM. TMI-005 (25 mg/kg twice per day) reduces tumor growth in an A549 mouse xenograft model when administered in combination with ionizing radiation.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Levin, J.I., Chen, J.M., and Cole, D.C. Acetylenic α-amino acid-based sulfonamide hydroxamic acid tace inhibitors. WO 00/44709, (2000).

    2. Shu, C., Zhou, H., Afsharvand, M., et al. Pharmacokinetic-pharmacodynamic modeling of apratastat: A population-based approach. J. Clin. Pharmacol. 51(4), 472-481 (2011).

    3. Sharma, A., Bender, S., Zimmerman, M., et al. Secretome signature identifies ADAM17 as novel target for radiosensitization of non-small cell lung cancer. Clin. Cancer Res. 22(17), 4428-4439 (2016).