Quisinostat HCl
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MedKoo CAT#: 201612

CAS#: 1083078-98-1 (HCl)

Description: Quisinostat, also known as JNJ-26481585, is an orally bioavailable, second-generation, hydroxamic acid-based inhibitor of histone deacetylase (HDAC) with potential antineoplastic activity. HDAC inhibitor JNJ-26481585 inhibits HDAC leading to an accumulation of highly acetylated histones, which may result in an induction of chromatin remodeling; inhibition of the transcription of tumor suppressor genes; inhibition of tumor cell division; and the induction of tumor cell apoptosis. HDAC, an enzyme upregulated in many tumor types, deacetylates chromatin histone proteins. Compared to some first generation HDAC inhibitors, JNJ-26481585 may induce superior HSP70 upregulation and bcl-2 downregulation.


Price and Availability

Size
Price

10mg
USD 150
100mg
USD 750
1g
USD 2950
Size
Price

25mg
USD 250
200mg
USD 1150
2g
USD 4150
Size
Price

50mg
USD 450
500mg
USD 1950
5g
Ask price

Quisinostat hydrochloride, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 201612
Name: Quisinostat HCl
CAS#: 1083078-98-1 (HCl)
Chemical Formula: C21H27ClN6O2
Exact Mass: 394.21172
Molecular Weight: 430.937
Elemental Analysis: C, 58.53; H, 6.32; Cl, 8.23; N, 19.50; O, 7.43


Related CAS #: 1083078-98-1 (HCl)   875320-29-9 (free base)   875320-31-3 (2HCl)    

Synonym: JNJ26481585; JNJ-26481585; JNJ 26481585; JNJ-26481585-AAC; Quisinostat HCl; Quisinostat hydrochloride.

IUPAC/Chemical Name: N-hydroxy-2-(4-((((1-methyl-1H-indol-3-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidine-5-carboxamide hydrochloride

InChi Key: TWNOICNTTFKOHQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H26N6O2.ClH/c1-26-14-17(18-4-2-3-5-19(18)26)11-22-10-15-6-8-27(9-7-15)21-23-12-16(13-24-21)20(28)25-29;/h2-5,12-15,22,29H,6-11H2,1H3,(H,25,28);1H

SMILES Code: O=C(C1=CN=C(N2CCC(CNCC3=CN(C)C4=C3C=CC=C4)CC2)N=C1)NO.[H]Cl


Technical Data

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).

Harmonized System Code:
293490


Additional Information

Related CAS#
875320-29-9 (Quisinostat free base)
1083078-98-1 (Quisinostat hydrochloride)
 


References

1: Capasso KE, Manners MT, Quershi RA, Tian Y, Gao R, Hu H, Barrett JE, Sacan A, Ajit SK. Effect of Histone Deacetylase Inhibitor JNJ-26481585 in Pain. J Mol Neurosci. 2014 Aug 2. [Epub ahead of print] PubMed PMID: 25085711.

2: Maes K, De Smedt E, Lemaire M, De Raeve H, Menu E, Van Valckenborgh E, McClue S, Vanderkerken K, De Bruyne E. The role of DNA damage and repair in decitabine-mediated apoptosis in multiple myeloma. Oncotarget. 2014 May 30;5(10):3115-29. PubMed PMID: 24833108; PubMed Central PMCID: PMC4102796.

3: Carol H, Gorlick R, Kolb EA, Morton CL, Manesh DM, Keir ST, Reynolds CP, Kang MH, Maris JM, Wozniak A, Hickson I, Lyalin D, Kurmasheva RT, Houghton PJ, Smith MA, Lock R. Initial testing (stage 1) of the histone deacetylase inhibitor, quisinostat (JNJ-26481585), by the Pediatric Preclinical Testing Program. Pediatr Blood Cancer. 2014 Feb;61(2):245-52. doi: 10.1002/pbc.24724. Epub 2013 Sep 4. PubMed PMID: 24038993.

4: Venugopal B, Baird R, Kristeleit RS, Plummer R, Cowan R, Stewart A, Fourneau N, Hellemans P, Elsayed Y, McClue S, Smit JW, Forslund A, Phelps C, Camm J, Evans TR, de Bono JS, Banerji U. A phase I study of quisinostat (JNJ-26481585), an oral hydroxamate histone deacetylase inhibitor with evidence of target modulation and antitumor activity, in patients with advanced solid tumors. Clin Cancer Res. 2013 Aug 1;19(15):4262-72. doi: 10.1158/1078-0432.CCR-13-0312. Epub 2013 Jun 5. PubMed PMID: 23741066.

5: Schreml J, Riessland M, Paterno M, Garbes L, Roßbach K, Ackermann B, Krämer J, Somers E, Parson SH, Heller R, Berkessel A, Sterner-Kock A, Wirth B. Severe SMA mice show organ impairment that cannot be rescued by therapy with the HDACi JNJ-26481585. Eur J Hum Genet. 2013 Jun;21(6):643-52. doi: 10.1038/ejhg.2012.222. Epub 2012 Oct 17. PubMed PMID: 23073311; PubMed Central PMCID: PMC3658191.

6: Stühmer T, Arts J, Chatterjee M, Borawski J, Wolff A, King P, Einsele H, Leo E, Bargou RC. Preclinical anti-myeloma activity of the novel HDAC-inhibitor JNJ-26481585. Br J Haematol. 2010 May;149(4):529-36. doi: 10.1111/j.1365-2141.2010.08126.x. Epub 2010 Mar 13. PubMed PMID: 20331455.

7: Arts J, King P, Mariën A, Floren W, Beliën A, Janssen L, Pilatte I, Roux B, Decrane L, Gilissen R, Hickson I, Vreys V, Cox E, Bol K, Talloen W, Goris I, Andries L, Du Jardin M, Janicot M, Page M, van Emelen K, Angibaud P. JNJ-26481585, a novel "second-generation" oral histone deacetylase inhibitor, shows broad-spectrum preclinical antitumoral activity. Clin Cancer Res. 2009 Nov 15;15(22):6841-51. doi: 10.1158/1078-0432.CCR-09-0547. Epub 2009 Oct 27. PubMed PMID: 19861438.

8: Tong WG, Wei Y, Stevenson W, Kuang SQ, Fang Z, Zhang M, Arts J, Garcia-Manero G. Preclinical antileukemia activity of JNJ-26481585, a potent second-generation histone deacetylase inhibitor. Leuk Res. 2010 Feb;34(2):221-8. doi: 10.1016/j.leukres.2009.07.024. Epub 2009 Aug 13. PubMed PMID: 19682743.

9: Deleu S, Lemaire M, Arts J, Menu E, Van Valckenborgh E, Vande Broek I, De Raeve H, Coulton L, Van Camp B, Croucher P, Vanderkerken K. Bortezomib alone or in combination with the histone deacetylase inhibitor JNJ-26481585: effect on myeloma bone disease in the 5T2MM murine model of myeloma. Cancer Res. 2009 Jul 1;69(13):5307-11. doi: 10.1158/0008-5472.CAN-08-4472. Epub 2009 Jun 16. PubMed PMID: 19531653.

10: Deleu S, Lemaire M, Arts J, Menu E, Van Valckenborgh E, King P, Vande Broek I, De Raeve H, Van Camp B, Croucher P, Vanderkerken K. The effects of JNJ-26481585, a novel hydroxamate-based histone deacetylase inhibitor, on the development of multiple myeloma in the 5T2MM and 5T33MM murine models. Leukemia. 2009 Oct;23(10):1894-903. doi: 10.1038/leu.2009.121. Epub 2009 Jun 4. PubMed PMID: 19494837.

11: Dedes KJ, Dedes I, Imesch P, von Bueren AO, Fink D, Fedier A. Acquired vorinostat resistance shows partial cross-resistance to 'second-generation' HDAC inhibitors and correlates with loss of histone acetylation and apoptosis but not with altered HDAC and HAT activities. Anticancer Drugs. 2009 Jun;20(5):321-33. doi: 10.1097/CAD.0b013e3283262a32. PubMed PMID: 19322073.

(last updated: 4/20/2016).