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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
Structure of OBP-801

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

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
FGFR inhibitor BGJ398 and HDAC inhibitor OBP-801 synergistically inhibit cell growth and induce apoptosis in bladder cancer cells.
2018 Feb

Sample Use Guides

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
OBP-801 potently inhibited HDAC enzyme with an IC50 of 2.0 nM in the presence of dithiothreitol.
Name Type Language
OBP-801
Common Name English
SPIRUCHOSTATIN A
Common Name English
YM-753
Code English
CYCLO(D-ALANYL-D-CYSTEINYL-(3S,4R)-4-AMINO-3-HYDROXY-5-METHYLHEXANOYL-(3S,4E)-3-HYDROXY-7-MERCAPTO-4-HEPTENOYL), CYCLIC (2->4)-DISULFIDE
Systematic Name English
Code System Code Type Description
DRUG BANK
DB12279
Created by admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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WIKIPEDIA
Spiruchostatin
Created by admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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EPA CompTox
DTXSID301029731
Created by admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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CAS
328548-11-4
Created by admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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PUBCHEM
11178958
Created by admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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FDA UNII
30Q3VS5HZ4
Created by admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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NCI_THESAURUS
C121665
Created by admin on Sat Dec 16 09:40:06 GMT 2023 , Edited by admin on Sat Dec 16 09:40:06 GMT 2023
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