Nanatinostat
Nanatinostat, also known as Tractinostat, CHR-3996 and VRx-3996, is an orally bioavailable, second-generation hydroxamic acid-based inhibitor of histone deacetylase (HDAC) with potential antineoplastic activity. HDAC inhibitor CHR-3996 inhibits HDAC, resulting in an accumulation of highly acetylated histones, the induction of chromatin remodeling, and the selective transcription of tumor suppressor genes; these events may result in the inhibition of tumor cell division and the induction of tumor cell apoptosis. This agent may upregulate HSP70 and downregulate anti-apoptotic Bcl-2 proteins more substantially than some first-generation HDAC inhibitors. HDACs, upregulated in many tumor cell types, are a family of metalloenzymes responsible for the deacetylation of chromatin histone proteins.
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Chemical Information
| Name | Nanatinostat |
|---|---|
| Iupac Chemical Name | 2-((1R,5S,6s)-6-(((6-fluoroquinolin-2-yl)methyl)amino)-3-azabicyclo[3.1.0]hexan-3-yl)-N-hydroxypyrimidine-4-carboxamide |
| Synonyms | CHR3996; CHR-3996; CHR 3996; VRx-3996; VRx3996; VRx 3996; Nanatinostat; Tractinostat; |
| Molecular Formula | C20H19FN6O2 |
| Molecular Weight | 394.40 |
| Smile | FC1=CC=C2N=C(CN[C@H]3[C@]4([H])CN(C5=NC=CC(C(NO)=O)=N5)C[C@]34[H])C=CC2=C1 |
| InChiKey | GTAUPYWUPNCTCZ-HWWDLCQESA-N |
| InChi | InChI=1S/C20H19FN6O2/c21-12-2-4-16-11(7-12)1-3-13(24-16)8-23-18-14-9-27(10-15(14)18)20-22-6-5-17(25-20)19(28)26-29/h1-7,14-15,18,23,29H,8-10H2,(H,26,28)/t14-,15+,18+ |
| CAS Number | 1256448-47-1 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Off-white solid |
|---|---|
| Purity | 98% Min. |
| Storage | Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years). |
| Solubility | Soluble in DMSO |
| Handling | |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
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| Mechanism | |
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| Clinical study |
1: Singh AN, Sharma N. Epigenetic Modulators as Potential Multi-targeted Drugs Against Hedgehog Pathway for Treatment of Cancer. Protein J. 2019 Oct;38(5):537-550. doi: 10.1007/s10930-019-09832-9. PMID: 30993446.
2: Garrido-Laguna I, Tometich D, Hu N, Ying J, Geiersbach K, Whisenant J, Wang K, Ross JS, Sharma S. N of 1 case reports of exceptional responders accrued from pancreatic cancer patients enrolled in first-in-man studies from 2002 through 2012. Oncoscience. 2015 Mar 14;2(3):285-93. doi: 10.18632/oncoscience.141. PMID: 25897431; PMCID: PMC4394134.
3: Smith EM, Zhang L, Walker BA, Davenport EL, Aronson LI, Krige D, Hooftman L, Drummond AH, Morgan GJ, Davies FE. The combination of HDAC and aminopeptidase inhibitors is highly synergistic in myeloma and leads to disruption of the NFκB signalling pathway. Oncotarget. 2015 Jul 10;6(19):17314-27. doi: 10.18632/oncotarget.1168. PMID: 26015393; PMCID: PMC4627310.
4: Banerji U, van Doorn L, Papadatos-Pastos D, Kristeleit R, Debnam P, Tall M, Stewart A, Raynaud F, Garrett MD, Toal M, Hooftman L, De Bono JS, Verweij J, Eskens FA. A phase I pharmacokinetic and pharmacodynamic study of CHR-3996, an oral class I selective histone deacetylase inhibitor in refractory solid tumors. Clin Cancer Res. 2012 May 1;18(9):2687-94. doi: 10.1158/1078-0432.CCR-11-3165. PMID: 22553374.
5: Moffat D, Patel S, Day F, Belfield A, Donald A, Rowlands M, Wibawa J, Brotherton D, Stimson L, Clark V, Owen J, Bawden L, Box G, Bone E, Mortenson P, Hardcastle A, van Meurs S, Eccles S, Raynaud F, Aherne W. Discovery of 2-(6-{[(6 -fluoroquinolin-2-yl)methyl]amino}bicyclo[3.1.0]hex-3-yl)-N-hydroxypyrimidine-5- carboxamide (CHR-3996), a class I selective orally active histone deacetylase inhibitor. J Med Chem. 2010 Dec 23;53(24):8663-78. doi: 10.1021/jm101177s. Epub 2010 Nov 16. PMID: 21080647.
6: Al-Shamahi A, Murch L, Kirkham K. American Society of Clinical Oncology--46th annual meeting. IDrugs. 2010 Aug;13(8):506-9. PMID: 20721815.
Chemical Structure
