WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H205626
CAS#: 929016-96-6
Description: Pracinostat, also known as SB939, is an orally bioavailable, small-molecule histone deacetylase (HDAC) inhibitor with potential antineoplastic activity. Pracinostat inhibits HDACs, which may result in the accumulation of highly acetylated histones, followed by the induction of chromatin remodeling; the selective transcription of tumor suppressor genes; the tumor suppressor protein-mediated inhibition of tumor cell division; and, finally, the induction of tumor cell apoptosis. In March 2014, pracinostat has granted Orphan Drug for acute myelocytic leukemia (AML) and for the treatment of T-cell lymphoma by the Food and Drug Administration.
Hodoodo Cat#: H205626
Name: Pracinostat
CAS#: 929016-96-6
Chemical Formula: C20H30N4O2
Exact Mass: 358.24
Molecular Weight: 358.478
Elemental Analysis: C, 67.01; H, 8.44; N, 15.63; O, 8.93
Synonym: SB939; SB 939; SC-939; Pracinostat.
IUPAC/Chemical Name: (E)-3-(2-butyl-1-(2-(diethylamino)ethyl)-1H-benzo[d]imidazol-5-yl)-N-hydroxyacrylamide
InChi Key: JHDKZFFAIZKUCU-ZRDIBKRKSA-N
InChi Code: InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+
SMILES Code: O=C(NO)/C=C/C1=CC=C2N(CCN(CC)CC)C(CCCC)=NC2=C1
Appearance: white 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:
| Biological target: | |
| In vitro activity: | |
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The following data is based on the product molecular weight 358.48 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.
| 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Rajak H, Singh A, Raghuwanshi K, Kumar R, Dewangan PK, Veerasamy R, Sharma PC, Dixit A, Mishra P. A Structural Insight into Hydroxamic Acid Based Histone Deacetylase Inhibitors for the Presence of Anticancer Activity. Curr Med Chem. 2013 Jul 24. [Epub ahead of print] PubMed PMID: 23895688.
2: Zorzi AP, Bernstein M, Samson Y, Wall DA, Desai S, Nicksy D, Wainman N, Eisenhauer E, Baruchel S. A phase I study of histone deacetylase inhibitor, pracinostat (SB939), in pediatric patients with refractory solid tumors: IND203 a trial of the NCIC IND program/C17 pediatric phase I consortium. Pediatr Blood Cancer. 2013 Nov;60(11):1868-74. doi: 10.1002/pbc.24694. Epub 2013 Jul 25. PubMed PMID: 23893953.
3: Okabe S, Tauchi T, Tanaka Y, Kimura S, Maekawa T, Ohyashiki K. Activity of histone deacetylase inhibitors and an Aurora kinase inhibitor in BCR-ABL-expressing leukemia cells: Combination of HDAC and Aurora inhibitors in BCR-ABL-expressing cells. Cancer Cell Int. 2013 Apr 4;13(1):32. doi: 10.1186/1475-2867-13-32. PubMed PMID: 23556431; PubMed Central PMCID: PMC3635933.
4: Novotny-Diermayr V, Hart S, Goh KC, Cheong A, Ong LC, Hentze H, Pasha MK, Jayaraman R, Ethirajulu K, Wood JM. The oral HDAC inhibitor pracinostat (SB939) is efficacious and synergistic with the JAK2 inhibitor pacritinib (SB1518) in preclinical models of AML. Blood Cancer J. 2012 May;2(5):e69. doi: 10.1038/bcj.2012.14. Epub 2012 May 4. PubMed PMID: 22829971; PubMed Central PMCID: PMC3366067.
5: Sumanadasa SD, Goodman CD, Lucke AJ, Skinner-Adams T, Sahama I, Haque A, Do TA, McFadden GI, Fairlie DP, Andrews KT. Antimalarial activity of the anticancer histone deacetylase inhibitor SB939. Antimicrob Agents Chemother. 2012 Jul;56(7):3849-56. doi: 10.1128/AAC.00030-12. Epub 2012 Apr 16. PubMed PMID: 22508312; PubMed Central PMCID: PMC3393387.
6: Quintás-Cardama A, Kantarjian H, Estrov Z, Borthakur G, Cortes J, Verstovsek S. Therapy with the histone deacetylase inhibitor pracinostat for patients with myelofibrosis. Leuk Res. 2012 Sep;36(9):1124-7. doi: 10.1016/j.leukres.2012.03.003. Epub 2012 Apr 2. PubMed PMID: 22475363.
7: Jayaraman R, Pilla Reddy V, Pasha MK, Wang H, Sangthongpitag K, Yeo P, Hu CY, Wu X, Xin L, Goh E, New LS, Ethirajulu K. Preclinical metabolism and disposition of SB939 (Pracinostat), an orally active histone deacetylase inhibitor, and prediction of human pharmacokinetics. Drug Metab Dispos. 2011 Dec;39(12):2219-32. doi: 10.1124/dmd.111.041558. Epub 2011 Aug 26. PubMed PMID: 21873472.
8: Wang H, Yu N, Chen D, Lee KC, Lye PL, Chang JW, Deng W, Ng MC, Lu T, Khoo ML, Poulsen A, Sangthongpitag K, Wu X, Hu C, Goh KC, Wang X, Fang L, Goh KL, Khng HH, Goh SK, Yeo P, Liu X, Bonday Z, Wood JM, Dymock BW, Kantharaj E, Sun ET. Discovery of (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl}-N-hydroxyacrylami de (SB939), an orally active histone deacetylase inhibitor with a superior preclinical profile. J Med Chem. 2011 Jul 14;54(13):4694-720. doi: 10.1021/jm2003552. Epub 2011 Jun 16. PubMed PMID: 21634430.
9: Novotny-Diermayr V, Sausgruber N, Loh YK, Pasha MK, Jayaraman R, Hentze H, Yong WP, Goh BC, Toh HC, Ethirajulu K, Zhu J, Wood JM. Pharmacodynamic evaluation of the target efficacy of SB939, an oral HDAC inhibitor with selectivity for tumor tissue. Mol Cancer Ther. 2011 Jul;10(7):1207-17. doi: 10.1158/1535-7163.MCT-11-0044. Epub 2011 May 17. PubMed PMID: 21586629.
10: Yong WP, Goh BC, Soo RA, Toh HC, Ethirajulu K, Wood J, Novotny-Diermayr V, Lee SC, Yeo WL, Chan D, Lim D, Seah E, Lim R, Zhu J. Phase I and pharmacodynamic study of an orally administered novel inhibitor of histone deacetylases, SB939, in patients with refractory solid malignancies. Ann Oncol. 2011 Nov;22(11):2516-22. doi: 10.1093/annonc/mdq784. Epub 2011 Mar 8. PubMed PMID: 21385886.
11: Razak AR, Hotte SJ, Siu LL, Chen EX, Hirte HW, Powers J, Walsh W, Stayner LA, Laughlin A, Novotny-Diermayr V, Zhu J, Eisenhauer EA. Phase I clinical, pharmacokinetic and pharmacodynamic study of SB939, an oral histone deacetylase (HDAC) inhibitor, in patients with advanced solid tumours. Br J Cancer. 2011 Mar 1;104(5):756-62. doi: 10.1038/bjc.2011.13. Epub 2011 Feb 1. PubMed PMID: 21285985; PubMed Central PMCID: PMC3048208.
12: Novotny-Diermayr V, Sangthongpitag K, Hu CY, Wu X, Sausgruber N, Yeo P, Greicius G, Pettersson S, Liang AL, Loh YK, Bonday Z, Goh KC, Hentze H, Hart S, Wang H, Ethirajulu K, Wood JM. SB939, a novel potent and orally active histone deacetylase inhibitor with high tumor exposure and efficacy in mouse models of colorectal cancer. Mol Cancer Ther. 2010 Mar;9(3):642-52. doi: 10.1158/1535-7163.MCT-09-0689. Epub 2010 Mar 2. PubMed PMID: 20197387.
