batimastat   Click here for help

GtoPdb Ligand ID: 5145

Synonyms: BB 94 | BB-94 | BB94
PDB Ligand
Compound class: Synthetic organic
Comment: Batimastat (BB-94) is a broad-spectrum matrix metalloprotease (MMP) inhibitor. It inhibits MMPs by binding the zinc ion in the active site of the enzymes.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 4
Rotatable bonds 15
Topological polar surface area 161.07
Molecular weight 477.18
XLogP 2.94
No. Lipinski's rules broken 1
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Canonical SMILES CNC(=O)C(NC(=O)C(C(C(=O)NO)CSc1cccs1)CC(C)C)Cc1ccccc1
Isomeric SMILES CNC(=O)[C@@H](NC(=O)[C@@H]([C@@H](C(=O)NO)CSc1cccs1)CC(C)C)Cc1ccccc1
InChI 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
1. Beattie GJ, Smyth JF. (1998)
Phase I study of intraperitoneal metalloproteinase inhibitor BB94 in patients with malignant ascites.
Clin Cancer Res, 4 (8): 1899-902. [PMID:9717817]
2. Castelhano AL, Billedeau R, Dewdney N, Donnelly S, Horne S, Kurz LJ, Liak T, Martin R, Uppington R, Zhengyu Yuan et al.. (1995)
Novel indolactam-based inhibitors of matrix metalloproteinases.
Bioorg Med Chem Lett, 5: 1415-1420. DOI: 10.1016/0960-894X(95)00233-J
3. Fray MJ, Dickinson RP, Huggins JP, Occleston NL. (2003)
A potent, selective inhibitor of matrix metalloproteinase-3 for the topical treatment of chronic dermal ulcers.
J Med Chem, 46 (16): 3514-25. [PMID:12877590]
4. Parsons SL, Watson SA, Steele RJ. (1997)
Phase I/II trial of batimastat, a matrix metalloproteinase inhibitor, in patients with malignant ascites.
Eur J Surg Oncol, 23 (6): 526-31. [PMID:9484924]
5. Wojtowicz-Praga S, Low J, Marshall J, Ness E, Dickson R, Barter J, Sale M, McCann P, Moore J, Cole A et al.. (1996)
Phase I trial of a novel matrix metalloproteinase inhibitor batimastat (BB-94) in patients with advanced cancer.
Invest New Drugs, 14 (2): 193-202. [PMID:8913840]
6. Yamamoto M, Tsujishita H, Hori N, Ohishi Y, Inoue S, Ikeda S, Okada Y. (1998)
Inhibition of membrane-type 1 matrix metalloproteinase by hydroxamate inhibitors: an examination of the subsite pocket.
J Med Chem, 41 (8): 1209-17. [PMID:9548812]