Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H19BN2O3.CH4O3S |
Molecular Weight | 310.175 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O
InChI
InChIKey=OXYYOEIGQRXGPI-WSZWBAFRSA-N
InChI=1S/C9H19BN2O3.CH4O3S/c1-6(2)8(11)9(13)12-5-3-4-7(12)10(14)15;1-5(2,3)4/h6-8,14-15H,3-5,11H2,1-2H3;1H3,(H,2,3,4)/t7-,8-;/m0./s1
Talabostat is a prolineboronate ester derivative patented by Boehringer Ingelheim Pharmaceuticals, Inc. as an antineoplastic agent. Talabostat inhibits dipeptidyl peptidases, such as fibroblast activation protein (FAP), resulting in the stimulation of cytokine and chemokine production and specific T-cell immunity and T-cell dependent activity. Talabostat has been shown to cause caspase-1 activation and IL-1β induction in macrophages, which in turn causes upregulation of the cytokines and chemokines that characterize the responses to talabostat, both in vitro and in tumor-bearing mice. Talabostat may also stimulate the production of colony stimulating factors, such as granulocyte colony stimulating factor (G-CSF), resulting in the stimulation of hematopoiesis. In clinical trials, the combination of talabostat and cisplatin was well tolerated compared to historical data using cisplatin alone. The most frequent adverse events were nausea, vomiting, fatigue, anemia, edema, and constipation. Unfortunately was no evidence that Talabostat enhanced the clinical activity of other anticancer drugs and further development was discontinued.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL284 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18783201 |
0.18 nM [Ki] | ||
Target ID: CHEMBL4657 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18783201 |
1.5 nM [Ki] | ||
Target ID: CHEMBL4793 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18783201 |
0.76 nM [Ki] |
PubMed
Title | Date | PubMed |
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Gateways to clinical trials. | 2007 Dec |
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HIV-1 Env vaccine comprised of electroporated DNA and protein co-administered with Talabostat. | 2008 May 23 |
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Inhibitor of DASH proteases affects expression of adhesion molecules in osteoclasts and reduces myeloma growth and bone disease. | 2009 Jun |
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From melanocyte to metastatic malignant melanoma. | 2010 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19643020
75-100 mg/m^2 cisplatin combined with 300-400 mcg talabostat bid for 6, 21-day cycle
Route of Administration:
Oral
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NCI_THESAURUS |
C783
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300000003700
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DBSALT001996
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CHEMBL67279
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RR-68
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150080-09-4
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C80682
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V8ZG4Y1B51
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ACTIVE MOIETY
SUBSTANCE RECORD