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
References
1. Layfield HJ, Williams HF, Ravishankar D, Mehmi A, Sonavane M, Salim A, Vaiyapuri R, Lakshminarayanan K, Vallance TM, Bicknell AB et al.. (2020)
Repurposing Cancer Drugs Batimastat and Marimastat to Inhibit the Activity of a Group I Metalloprotease from the Venom of the Western Diamondback Rattlesnake, Crotalus atrox.
Toxins (Basel), 12 (5). DOI: 10.3390/toxins12050309 [PMID:32397419]
2. Rasmussen HS, McCann PP. (1997)
Matrix metalloproteinase inhibition as a novel anticancer strategy: a review with special focus on batimastat and marimastat.
Pharmacol Ther, 75 (1): 69-75. [PMID:9364582]
3. Sparano JA, Bernardo P, Stephenson P, Gradishar WJ, Ingle JN, Zucker S, Davidson NE. (2004)
Randomized phase III trial of marimastat versus placebo in patients with metastatic breast cancer who have responding or stable disease after first-line chemotherapy: Eastern Cooperative Oncology Group trial E2196.
J Clin Oncol, 22 (23): 4683-90. [PMID:15570070]
4. Steward WP, Thomas AL. (2000)
Marimastat: the clinical development of a matrix metalloproteinase inhibitor.
Expert Opin Investig Drugs, 9 (12): 2913-22. [PMID:11093361]
5. Williams HF, Layfield HJ, Vallance T, Patel K, Bicknell AB, Trim SA, Vaiyapuri S. (2019)
The Urgent Need to Develop Novel Strategies for the Diagnosis and Treatment of Snakebites.
Toxins (Basel), 11 (6). [PMID:31226842]