Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H31N3O6S2 |
Molecular Weight | 473.607 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@H]1NC(=O)[C@H]2CSSCC\C=C\[C@H](CC(=O)N[C@H](C)C(=O)N2)OC(=O)C[C@@H]1O
InChI
InChIKey=XFLBOEMFLGLWFF-HDXRNPEWSA-N
InChI=1S/C20H31N3O6S2/c1-11(2)18-15(24)9-17(26)29-13-6-4-5-7-30-31-10-14(20(28)23-18)22-19(27)12(3)21-16(25)8-13/h4,6,11-15,18,24H,5,7-10H2,1-3H3,(H,21,25)(H,22,27)(H,23,28)/b6-4+/t12-,13-,14-,15+,18-/m1/s1
OBP-801 (spiruchostatin A) is an inhibitor of histone deacetylase (HDAC) enzymes, with potential antineoplastic activity. OBP-801 was originally identified as an enhancer of PAI-1 gene expression and was established as a new HDAC inhibitor by a p21 promoter reporter screen. Upon administration, OBP-801 inhibits the activity of HDACs; this results in an accumulation of highly acetylated chromatin histones, the induction of chromatin remodeling and an altered pattern of gene expression. This leads to selective transcription of tumor suppressor genes, tumor suppressor protein-mediated inhibition of tumor cell division and induction of tumor cell apoptosis. This may inhibit proliferation of susceptible tumor cells. HDAC, which is upregulated in many tumor cell types, deacetylates chromatin histone proteins. OBP‑801 induces M‑phase arrest and apoptosis in rhabdomyosarcoma cells. OBP‑801 is expected to show anticancer effect by promoting an expression of tumor suppressor genes in cancer cell and inducing apoptotic and autophagic cell death. The results of pre-clinical studies on OBP-801 indicated the most potent HDAC inhibitory activity as compared to other HDAC inhibitors including and Zolinza® and Istodax®, and its efficacy on a wide range of cancers is expected. Furthermore, Oncolys has been exploring the potential ophthalmic use of OBP-801 in collaboration with Kyoto Prefectural University of Medicine. OBP-801 has been used in trials studying the treatment of solid tumor.
Originator
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
A novel HDAC inhibitor OBP-801 and a PI3K inhibitor LY294002 synergistically induce apoptosis via the suppression of survivin and XIAP in renal cell carcinoma. | 2013 Oct |
|
The histone deacetylase inhibitor OBP-801 and eribulin synergistically inhibit the growth of triple-negative breast cancer cells with the suppression of survivin, Bcl-xL, and the MAPK pathway. | 2018 Aug |
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FGFR inhibitor BGJ398 and HDAC inhibitor OBP-801 synergistically inhibit cell growth and induce apoptosis in bladder cancer cells. | 2018 Feb |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18292931
OBP-801 was given as a single intravenous
administration at a dose of 3 mg/kg to the WiDrbearing
nude mice
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18292931
OBP-801 potently inhibited HDAC enzyme with an IC50 of 2.0 nM in the presence of dithiothreitol.
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DB12279
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Spiruchostatin
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DTXSID301029731
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328548-11-4
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11178958
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30Q3VS5HZ4
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C121665
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SUBSTANCE RECORD