MedKoo Cat#: 205771 | Name: Nanatinostat TFA

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Nanatinostat TFA
Nanatinostat TFA
CAS#1256448-48-2 (TFA)

Theoretical Analysis

MedKoo Cat#: 205771

Name: Nanatinostat TFA

CAS#: 1256448-48-2 (TFA)

Chemical Formula: C22H20F4N6O4

Exact Mass: 393.1601

Molecular Weight: 508.43

Elemental Analysis: C, 51.97; H, 3.97; F, 14.95; N, 16.53; O, 12.59

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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; Nanatinostat TFA; Nanatinostat trifluoroacetic acid;
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 trfluoroacetic acid
InChi Key
WNMHEOGBNZYJGD-MPSOVPLESA-N
InChi Code
InChI=1S/C20H19FN6O2.C2HF3O2/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;3-2(4,5)1(6)7/h1-7,14-15,18,23,29H,8-10H2,(H,26,28);(H,6,7)/t14-,15+,18+;
SMILES Code
O=C(C1=NC(N2C[C@]3([H])[C@@H](NCC4=NC5=CC=C(F)C=C5C=C4)[C@]3([H])C2)=NC=C1)NO.O=C(O)C(F)(F)F
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, not in water
Shelf Life
>2 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
More Info
CHR-3996 is an optimised HDAC Inhibitor for Treatment of Cancers. Histone Deacetylases (HDACs) are a family of metalloenzymes that are able to Deacetylase Histones, leading to repression of gene expression. Inhibition of HDACs has been shown to impact multiple aspects of tumour progression. First generation HDAC inhibitors have demonstrated the clinical utility of this class, but in many cases lack optimal pharmaceutical characteristics. CHR-3996 is a potent, orally-active, pharmaceutically optimised class I HDAC selective inhibitor. CHR-3996 was entered into clinical development in 2008.  (source: http://www.chromatherapeutics.com/CHR-3996.htm).      

Preparing Stock Solutions

The following data is based on the product molecular weight 508.43 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
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.