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 [3,5]. Most recently marimastat has been reported to inhibit certain snake venom metalloproteases [2], with the implication that it could be repurposed as an antidote to snake venom poisoning [6].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Buchler A, Ismailani US, MacMullin N, Abdirahman F, Adi M, Bi C, Jany C, Keillor JW, Rotstein BH. (2023)
Quinazoline-2-Carboxamides as Selective PET Radiotracers for Matrix Metalloproteinase-13 Imaging in Atherosclerosis.
J Med Chem, 66 (10): 6682-6696. [PMID:37158732]
2. 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]
3. 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]
4. 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]
5. Steward WP, Thomas AL. (2000)
Marimastat: the clinical development of a matrix metalloproteinase inhibitor.
Expert Opin Investig Drugs, 9 (12): 2913-22. [PMID:11093361]
6. 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]