Nanatinostat
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MedKoo CAT#: 462355

CAS#: 1256448-47-1 (free base)

Description: 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.


Chemical Structure

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Nanatinostat
CAS# 1256448-47-1 (free base)

Theoretical Analysis

MedKoo Cat#: 462355
Name: Nanatinostat
CAS#: 1256448-47-1 (free base)
Chemical Formula: C20H19FN6O2
Exact Mass: 394.1554
Molecular Weight: 394.4104
Elemental Analysis: C, 60.91; H, 4.86; F, 4.82; N, 21.31; O, 8.11

Price and Availability

Size Price Availability Quantity
5.0mg USD 650.0 2 Weeks
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Related CAS #: 914937-68-1 (racemic)   1256448-47-1 (free base)   1256448-48-2 (TFA)   2648504-17-8 (hydrate)   1235859-13-8 (deleted)    

Synonym: CHR3996; CHR-3996; CHR 3996; VRx-3996; VRx3996; VRx 3996; Nanatinostat; Tractinostat;

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

InChi Key: GTAUPYWUPNCTCZ-HWWDLCQESA-N

InChi Code: 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+

SMILES Code: 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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

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.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 394.4104 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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.