A broad-spectrum inhibitor of MMPs and TACE
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Marimastat

Item No. 14869

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S,3R)-N4-[(1S)-2,2-dimethyl-1-[(methylamino)carbonyl]propyl]-N1,2-dihydroxy-3-(2-methylpropyl)-butanediamide
CAS Number
154039-60-8
Synonyms
  • BB-2516
  • KB-R8898
Molecular Formula
C15H29N3O5
Formula Weight
331.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlEthanol: 2 mg/ml
SMILES
CC(C)(C)[C@@H](C(NC)=O)NC([C@H](CC(C)C)[C@@H](C(NO)=O)O)=O
InChi Code
InChI=1S/C15H29N3O5/c1-8(2)7-9(10(19)13(21)18-23)12(20)17-11(14(22)16-6)15(3,4)5/h8-11,19,23H,7H2,1-6H3,(H,16,22)(H,17,20)(H,18,21)/t9-,10+,11-/m1/s1
InChi Key
OCSMOTCMPXTDND-OUAUKWLOSA-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

    $167

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    10 mg

    $259

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    25 mg

    $469

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    Cayman Chemical
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    Product Description

    Marimastat is a broad-spectrum matrix metalloproteinase (MMP) inhibitor (IC50s = 5, 6, 230, 16, and 3 nM for MMP-1, MMP-2, MMP-3, MMP-7, and MMP-9, respectively).1 It also binds to a recombinantly expressed catalytic domain of human MMP-14 (MMP-14cat; Ki = 2.1 nM) and inhibits gelatinases (IC50s = 3–6 nM), fibroblast collagenase (IC50 = 5 nM), and matrylisin (IC50 = 16 nM).2 It inhibits peritoneal dissemination of implanted human gastric carcinoma TMK-1 cells in nude mice (18 mg/kg per day) but does not affect TMK-1 viability in vitro, providing only 2.64% inhibition when used at a concentration of 10 μM.3 Marimastat inhibits lymph node metastasis in an oral squamous cell carcinoma (OSCC) OSC-19 mouse xenograft model (30 mg/kg per day).4 It also delays tumor growth of human head and neck squamous cell SCC-1 xenografts in nude mice alone and when combined with chemoradiation when administered at a dose of 8.7 mg/kg per day.5 Marimastat is an inhibitor of tumor necrosis factor alpha (TNF-α) convertase (TACE), which catalyzes pro-TNF-α conversion into TNF-α (IC50s = 3.8 and 7,000 nM for purified TACE and whole blood, respectively).6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Rasmussen, H.S., and McCann, P.P. Matrix metalloproteinase inhibition as a novel anticancer strategy: A review with special focus on batimastat and marimastat. Pharmacol. Ther. 75(1), 69-75 (1997).

    2. Toth, M., Bernardo, M.M., Gervasi, D.C., et al. Tissue inhibitor of metalloproteinase (TIMP)-2 acts synergistically with synthetic matrix metalloproteinase (MMP) inhibitors but not with TIMP-4 to enhance the (Membrane type 1)-MMP-dependent activation of pro-MMP-2. The Journal of Biological Chemisty 275(52), 41415-41423 (2000).

    3. Kimata, M., Otani, Y., Kubota, T., et al. Matrix metalloproteinase inhibitor, marimastat, decreases peritoneal spread of gastric carcinoma in nude mice. Jpn. J. Cancer Res. 93(7), 834-841 (2002).

    4. Maekawa, K., Sato, H., Furukawa, M., et al. Inhibition of cervical lymph node metastasis by marimastat (BB-2516) in an orthotopic oral squamous cell carcinoma implantation model. Clin. Exp. Metastasis 19(6), 513-518 (2002).

    5. Skipper, J.B., McNally, L.R., Rosenthal, E.L., et al. In vivo efficacy of marimastat and chemoradiation in head and neck cancer xenografts. ORL J. Otorhinolaryngol. Relat. Spec. 71(1), 1-5 (2009).

    6. Barlaam, B., Bird, T.G., Lambert-Van Der Brempt, C., et al. New α-substituted succinate-based hydroxamic acids as TNFα convertase inhibitors. J. Med. Chem. 42(23), 4890-4908 (1999).