marimastat   Click here for help

GtoPdb Ligand ID: 5220

Synonyms: BB-2516 | BB2516
PDB Ligand
Compound class: Synthetic organic
Comment: Marimastat (BB-2516) is a broad spectrum matrix metalloprotease (MMP) inhibitor. Its MMP inhibitory action has been applied to treating cancer [2,4]. Most recently marimastat has been reported to inhibit certain snake venom metalloproteases [1], with the implication that it could be repurposed as an antidote to snake venom poisoning [5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 5
Rotatable bonds 11
Topological polar surface area 127.76
Molecular weight 331.21
XLogP 0.35
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES ONC(=O)C(C(C(=O)NC(C(C)(C)C)C(=O)NC)CC(C)C)O
Isomeric SMILES ONC(=O)[C@H]([C@H](C(=O)N[C@@H](C(C)(C)C)C(=O)NC)CC(C)C)O
InChI 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
No information available.
Summary of Clinical Use Click here for help
Marimastat has completed Phase 3 evaluations in lung and breast cancers. A Phase 1 study (3 patients) has investigated the effects of marimastat as an option to treat disabling vascular anomalies in patients for whom there are no other available therapeutics.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT00261391 Phase I Drug Trial for S/E of Marimastat in Disabling Malformations When no Other Options. Phase 1 Interventional Boston Children’s Hospital
NCT00003011 Marimastat Following Chemotherapy in Treating Patients With Small Cell Lung Cancer Phase 3 Interventional Canadian Cancer Trials Group
NCT00002911 Marimastat in Treating Patients With Stage III Non-small Cell Lung Cancer Phase 3 Interventional National Cancer Institute (NCI)
NCT00003010 Marimastat or No Further Therapy in Treating Women With Metastatic Breast Cancer That Is Responding or Stable Following Chemotherapy Phase 3 Interventional Eastern Cooperative Oncology Group In this study, marimastat did not prolong progression-free survival when used after first-line chemotherapy for metastatic breast cancer. 3