A potent broad spectrum inhibitor of MMPs
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Batimastat

Item No. 14742

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2R,3S)-N4-hydroxy-N1-[(1S)-2-(methylamino)-2-oxo-1-(phenylmethyl)ethyl]-2-(2-methylpropyl)-3-[(2-thienylthio)methyl]-butanediamide
CAS Number
130370-60-4
Synonyms
  • BB-94
Molecular Formula
C23H31N3O4S2
Formula Weight
477.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 2 mg/ml
λmax
269 nm
SMILES
O=C(N[C@@H](CC1=CC=CC=C1)C(NC)=O)[C@H](CC(C)C)[C@@H](C(NO)=O)CSC2=CC=CS2
InChi Code
InChI=1S/C23H31N3O4S2/c1-15(2)12-17(18(22(28)26-30)14-32-20-10-7-11-31-20)21(27)25-19(23(29)24-3)13-16-8-5-4-6-9-16/h4-11,15,17-19,30H,12-14H2,1-3H3,(H,24,29)(H,25,27)(H,26,28)/t17-,18+,19+/m1/s1
InChi Key
XFILPEOLDIKJHX-QYZOEREBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Cayman Chemical
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    Product Description

    Batimastat is a broad spectrum inhibitor of matrix metalloproteinases (MMP), with IC50 values of 1-5 nM for all MMPs tested, including MMP-1, -2, -3, -7, -9, -13, and -14.1,2,3,4 It also potently inhibits TNFα-converting enzyme (IC50 = 14.9 nM).2 Because of its action on MMPs, batimastat has anti-proliferative, anti-invasive, and anti-metastatic actions that are relevant, in particular, to cancer.5 Batimastat less effectively inhibits the processing of the low affinity IgE receptor CD23 (IC50 = 100 nM).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Fray, M.J., Burslem, M.F., and Dickinson, R.P. Selectivity of inhibition of matrix metalloproteases MMP-3 and MMP-2 by succinyl hydroxamates and their carboxylic acid analogues is dependent on P3' group chirality. Bioorg. Med. Chem. Lett. 11(4), 567-570 (2001).

    2. Fray, M.J., Dickinson, R.P., Huggins, J.P., et al. A potent, selective inhibitor of matrix metalloproteinase-3 for the topical treatment of chronic dermal ulcers. J. Med. Chem. 46(16), 3514-3525 (2003).

    3. Sheppard, G.S., Florjancic, A.S., Giesler, J.R., et al. Aryl ketones as novel replacements for the C-terminal amide bond of succinyl hydroxamate MMP inhibitors. Bioorg. Med. Chem. Lett. 8(22), 3251-3256 (1998).

    4. Yamamoto, M., Tsujishita, H., Hori, N., et al. Inhibition of membrane-type 1 matrix metalloproteinase by hydroxamate inhibitors: An examination of the subsite pocket. J. Med. Chem. 41(8), 1209-1217 (1998).

    5. Chaudhary, A.K., Pandya, S., Ghosh, K., et al. Matrix metalloproteinase and its drug targets therapy in solid and hematological malignancies: An overview. Mutat. Res. 753(1), 7-23 (2013).

    6. Bailey, S., Bolognese, B., Buckle, D.R., et al. Selective inhibition of low affinity IgE receptor (CD23) processing. Bioorg. Med. Chem. Lett. 8(1), 29-34 (1998).