Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H31N3O4S2 |
| Molecular Weight | 477.64 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(C)C)[C@H](CSC2=CC=CS2)C(=O)NO
InChI
InChIKey=XFILPEOLDIKJHX-QYZOEREBSA-N
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
| Molecular Formula | C23H31N3O4S2 |
| Molecular Weight | 477.64 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9484924 | https://www.ncbi.nlm.nih.gov/pubmed/12877590 | https://www.ncbi.nlm.nih.gov/pubmed/8913840 | https://www.ncbi.nlm.nih.gov/pubmed/10100701 | https://www.ncbi.nlm.nih.gov/pubmed/9873712
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9484924 | https://www.ncbi.nlm.nih.gov/pubmed/12877590 | https://www.ncbi.nlm.nih.gov/pubmed/8913840 | https://www.ncbi.nlm.nih.gov/pubmed/10100701 | https://www.ncbi.nlm.nih.gov/pubmed/9873712
Batimastat is a powerful broad spectrum hydroxamate-type matrix metalloproteinases inhibitor(MMPI), with potent anticancer activity. Batimastat inhibits the growth and spread of lung tumors, breast cancer regrowth, and human colon tumor growth and spread in mouse models. Batimastat reduces MMP-mediated vascular dysfunction and vessel wall damage and enhances the sealing ability and bond strength of dental adhesives. Batimastat was the first MMPIs evaluated in cancer patients and to be used in a clinical trial. Batimastat was administered by the intraperitoneal and intra-pleural route in clinical trials. The Phase I and II clinical trials of Batimastat, when administered intraperitoneally, did not show a good response. Due to its poor water solubility, it is not well accepted for cancer treatment.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL332 |
0.99 nM [IC50] | ||
Target ID: CHEMBL333 |
0.73 nM [IC50] | ||
Target ID: CHEMBL283 |
0.56 nM [IC50] | ||
Target ID: CHEMBL4073 |
2.4 nM [IC50] | ||
Target ID: CHEMBL321 |
0.6 nM [IC50] | ||
Target ID: CHEMBL280 |
5.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Tyrosine phosphorylation and proteolysis. Pervanadate-induced, metalloprotease-dependent cleavage of the ErbB-4 receptor and amphiregulin. | 1998 Aug 7 |
|
| HIV-1 Tat neurotoxicity is prevented by matrix metalloproteinase inhibitors. | 2001 Feb |
|
| Decreased expression of membrane IL-5 receptor alpha on human eosinophils: II. IL-5 down-modulates its receptor via a proteinase-mediated process. | 2002 Dec 1 |
|
| Metalloproteinase-dependent transforming growth factor-alpha release mediates neurotensin-stimulated MAP kinase activation in human colonic epithelial cells. | 2004 Oct 15 |
|
| Metalloproteinases and transforming growth factor-alpha mediate substance P-induced mitogen-activated protein kinase activation and proliferation in human colonocytes. | 2004 Oct 29 |
|
| Elastin-derived peptides enhance angiogenesis by promoting endothelial cell migration and tubulogenesis through upregulation of MT1-MMP. | 2005 Jan 15 |
|
| MAO-A-induced mitogenic signaling is mediated by reactive oxygen species, MMP-2, and the sphingolipid pathway. | 2007 Jul 1 |
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| Inhibition of estrogen-induced pituitary tumor growth and angiogenesis in Fischer 344 rats by the matrix metalloproteinase inhibitor batimastat. | 2007 Mar |
|
| Matrix metalloproteinase inhibition facilitates cell death in intracerebral hemorrhage in mouse. | 2008 Apr |
|
| Characterisation of acetylcholinesterase release from neuronal cells. | 2013 Mar 25 |
Sample Use Guides
Batimastat was administered at 600, 1200 and 1800 mg/m^2 to consecutive groups of 3 patients once every 4 weeks
Route of Administration:
Intravenous
MCF-7 breast cancer cells were seeded in 24-well multidishes in growth medium and allowed to adhere for two days. When experiments were initiated (day 0), growth medium containing fulvestrant (0.1 μM), HER ligands (10 ng/ml), BB-94 (Batimastat, 10 μM) were added. The control cells were added similar amount of vehicle as the treated cells. Growth medium was replaced on day three, and cell number was deter¬mined on day five, using a crystal violet colorimetric assay. Batimastat shows potent anticancer activity.
| Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 18:01:26 UTC 2023
by
admin
on
Sat Dec 16 18:01:26 UTC 2023
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| Record UNII |
BK349F52C9
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| Record Status |
Validated (UNII)
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| Record Version |
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C1970
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GG-47
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100000086108
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Batimastat
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5362422
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