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 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
805 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
600 mg/m² single, intraperitoneal dose: 600 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1225 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
1200 mg/m² single, intraperitoneal dose: 1200 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1570 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
1800 mg/m² single, intraperitoneal dose: 1800 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
160877 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
600 mg/m² single, intraperitoneal dose: 600 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
371783 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
1200 mg/m² single, intraperitoneal dose: 1200 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
362140 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
1800 mg/m² single, intraperitoneal dose: 1800 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
522 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
600 mg/m² single, intraperitoneal dose: 600 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
577 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
1200 mg/m² single, intraperitoneal dose: 1200 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
449 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
1800 mg/m² single, intraperitoneal dose: 1800 mg/m² route of administration: Intraperitoneal experiment type: SINGLE co-administered: |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8913840/ |
BATIMASTAT serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 mg/m2 single, intrapleural Highest studied dose|Studied dose Dose: 300 mg/m2 Route: intrapleural Route: single Dose: 300 mg/m2 Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: Fever, elevation of AST... Other AEs: Fever (3 patients) Sources: elevation of AST (3 patients) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Fever | 3 patients | 300 mg/m2 single, intrapleural Highest studied dose|Studied dose Dose: 300 mg/m2 Route: intrapleural Route: single Dose: 300 mg/m2 Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| elevation of AST | 3 patients | 300 mg/m2 single, intrapleural Highest studied dose|Studied dose Dose: 300 mg/m2 Route: intrapleural Route: single Dose: 300 mg/m2 Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterisation of acetylcholinesterase release from neuronal cells. | 2013-03-25 |
|
| Matrix metalloproteinase inhibition facilitates cell death in intracerebral hemorrhage in mouse. | 2008-04 |
|
| MAO-A-induced mitogenic signaling is mediated by reactive oxygen species, MMP-2, and the sphingolipid pathway. | 2007-07-01 |
|
| Inhibition of estrogen-induced pituitary tumor growth and angiogenesis in Fischer 344 rats by the matrix metalloproteinase inhibitor batimastat. | 2007-03 |
|
| Elastin-derived peptides enhance angiogenesis by promoting endothelial cell migration and tubulogenesis through upregulation of MT1-MMP. | 2005-01-15 |
|
| Metalloproteinases and transforming growth factor-alpha mediate substance P-induced mitogen-activated protein kinase activation and proliferation in human colonocytes. | 2004-10-29 |
|
| Metalloproteinase-dependent transforming growth factor-alpha release mediates neurotensin-stimulated MAP kinase activation in human colonic epithelial cells. | 2004-10-15 |
|
| Decreased expression of membrane IL-5 receptor alpha on human eosinophils: II. IL-5 down-modulates its receptor via a proteinase-mediated process. | 2002-12-01 |
|
| HIV-1 Tat neurotoxicity is prevented by matrix metalloproteinase inhibitors. | 2001-02 |
|
| Tyrosine phosphorylation and proteolysis. Pervanadate-induced, metalloprotease-dependent cleavage of the ErbB-4 receptor and amphiregulin. | 1998-08-07 |
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
by
admin
on
Edited
Wed Apr 02 09:57:03 GMT 2025
by
admin
on
Wed Apr 02 09:57:03 GMT 2025
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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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NCI_THESAURUS |
C1970
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DTXSID20156497
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C080985
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130370-60-4
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CHEMBL279786
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SUB05669MIG
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C1529
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m2276
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GG-47
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Batimastat
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5362422
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It also potently inhibits TNF?-converting enzyme (IC50 = 14.9 nM).
IC50
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ACTIVE MOIETY |
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