MedKoo Cat#: 598397 | Name: Dacinostat HCl

Description:

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

Dacinostat, also known as LAQ824, is a hydroxamate histone deacetylase inhibitor with potential anticancer activity. LAQ824 sensitized nonsmall cell lung cancer to the cytotoxic effects of ionizing radiation. LAQ824 reduced clonogenic survival of the H23 and H460 cell lines five-fold compared with controls and four-fold compared with either agent alone (P<0.001). In phase I trials, LAQ824 was well tolerated at doses that induced accumulation of histone acetylation, with higher doses inducing changes consistent with HSP90 inhibition.

Chemical Structure

Dacinostat HCl
Dacinostat HCl
CAS#Dacinostat HCl

Theoretical Analysis

MedKoo Cat#: 598397

Name: Dacinostat HCl

CAS#: Dacinostat HCl

Chemical Formula: C22H26ClN3O3

Exact Mass: 379.1896

Molecular Weight: 415.92

Elemental Analysis: C, 63.53; H, 6.30; Cl, 8.52; N, 10.10; O, 11.54

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 #
404951-53-7 (free base) 591207-53-3 (free base) Dacinostat HCl 927176-79-2 (TFA) 1347751-13-6 (lactate)
Synonym
Dacinostat HCl; NVP-LAQ824; NVP-LAQ 824; NVP-LAQ-824; LAQ-824; LAQ824; LAQ 824; Dacinostat.
IUPAC/Chemical Name
(E)-3-(4-(((2-(1H-indol-2-yl)ethyl)(2-hydroxyethyl)amino)methyl)phenyl)-N-hydroxyacrylamide hydrochloride
InChi Key
CNOQMCROJPARKN-RRABGKBLSA-N
InChi Code
InChI=1S/C22H25N3O3.ClH/c26-14-13-25(12-11-20-15-19-3-1-2-4-21(19)23-20)16-18-7-5-17(6-8-18)9-10-22(27)24-28;/h1-10,15,23,26,28H,11-14,16H2,(H,24,27);1H/b10-9+;
SMILES Code
O=C(NO)/C=C/C1=CC=C(CN(CCC(N2)=CC3=C2C=CC=C3)CCO)C=C1.[H]Cl
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 415.92 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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Histone Deacetylase Inhibitors Restore Cancer Cell Sensitivity towards T Lymphocytes Mediated Cytotoxicity in Pancreatic Cancer. Cancers (Basel). 2022 Jul 29;14(15):3709. doi: 10.3390/cancers14153709. PMID: 35954379; PMCID: PMC9367398. 5: Sun Y, Yan K, Wang Y, Xu C, Wang D, Zhou W, Guo S, Han Y, Tang L, Shao Y, Shan S, Zhang QC, Tang Y, Zhang L, Xi Q. Context-dependent tumor-suppressive BMP signaling in diffuse intrinsic pontine glioma regulates stemness through epigenetic regulation of CXXC5. Nat Cancer. 2022 Sep;3(9):1105-1122. doi: 10.1038/s43018-022-00408-8. Epub 2022 Aug 1. PMID: 35915262. 6: Liu F, Yu J, Zhang YX, Li F, Liu Q, Zhou Y, Huang S, Fang H, Xiao Z, Liao L, Xu J, Wu XY, Wu F. High-throughput tandem-microwell assay for ammonia repositions FDA-Approved drugs to inhibit Helicobacter pylori urease. FASEB J. 2021 Nov;35(11):e21967. doi: 10.1096/fj.202100465RR. PMID: 34613630. 7: Chu XY, Zhang CC, Zhang RX, Zhang JF, Xia B, Wu JW. Identification of Dacinostat as a potential anti-obesity compound through transcriptional activation of adipose thermogenesis in mice. Biochim Biophys Acta Mol Basis Dis. 2021 Sep 1;1867(9):166169. doi: 10.1016/j.bbadis.2021.166169. Epub 2021 May 15. PMID: 34000373. 8: Chaudhuri S, Fowler MJ, Baker C, Stopka SA, Regan MS, Sablatura L, Broughton CW, Knight BE, Stabenfeldt SE, Agar NYR, Sirianni RW. β-Cyclodextrin-poly (β-Amino Ester) Nanoparticles Are a Generalizable Strategy for High Loading and Sustained Release of HDAC Inhibitors. ACS Appl Mater Interfaces. 2021 May 12;13(18):20960-20973. doi: 10.1021/acsami.0c22587. Epub 2021 Apr 27. PMID: 33905245; PMCID: PMC8153536. 9: Cianferotti C, Faltoni V, Cini E, Ermini E, Migliorini F, Petricci E, Taddei M, Salvini L, Battistuzzi G, Milazzo FM, Anastasi AM, Chiapparino C, De Santis R, Giannini G. Antibody drug conjugates with hydroxamic acid cargos for histone deacetylase (HDAC) inhibition. Chem Commun (Camb). 2021 Jan 28;57(7):867-870. doi: 10.1039/d0cc06131j. PMID: 33433550. 10: Dushanan R, Weerasinghe S, Dissanayake DP, Senthilinithy R. Cracking a cancer code histone deacetylation in epigenetic: the implication from molecular dynamics simulations on efficacy assessment of histone deacetylase inhibitors. J Biomol Struct Dyn. 2022 Mar;40(5):2352-2368. doi: 10.1080/07391102.2020.1838328. Epub 2020 Nov 2. PMID: 33131428. 11: Rice CA, Colon BL, Chen E, Hull MV, Kyle DE. Discovery of repurposing drug candidates for the treatment of diseases caused by pathogenic free-living amoebae. PLoS Negl Trop Dis. 2020 Sep 24;14(9):e0008353. doi: 10.1371/journal.pntd.0008353. PMID: 32970675; PMCID: PMC7546510. 12: Zhang S, Gong Z, Oladimeji PO, Currier DG, Deng Q, Liu M, Chen T, Li Y. A high-throughput screening identifies histone deacetylase inhibitors as therapeutic agents against medulloblastoma. Exp Hematol Oncol. 2019 Nov 15;8:30. doi: 10.1186/s40164-019-0153-x. PMID: 31788346; PMCID: PMC6858705. 13: Mao Y, Zhou J, Liu X, Gu E, Zhang Z, Tao W. Comparison of Different Histone Deacetylase Inhibitors in Attenuating Inflammatory Pain in Rats. Pain Res Manag. 2019 Jan 27;2019:1648919. doi: 10.1155/2019/1648919. Erratum in: Pain Res Manag. 2021 May 24;2021:9760961. PMID: 30809320; PMCID: PMC6369477. 14: Samiec M, Skrzyszowska M. Intrinsic and extrinsic molecular determinants or modulators for epigenetic remodeling and reprogramming of somatic cell-derived genome in mammalian nuclear-transferred oocytes and resultant embryos. Pol J Vet Sci. 2018 Mar;21(1):217-227. doi: 10.24425/119040. PMID: 29624006. 15: Sixto-López Y, Bello M, Correa-Basurto J. Insights into structural features of HDAC1 and its selectivity inhibition elucidated by Molecular dynamic simulation and Molecular Docking. J Biomol Struct Dyn. 2019 Feb;37(3):584-610. doi: 10.1080/07391102.2018.1441072. Epub 2018 Mar 6. PMID: 29447615. 16: Garmpis N, Damaskos C, Garmpi A, Dimitroulis D, Spartalis E, Margonis GA, Schizas D, Deskou I, Doula C, Magkouti E, Andreatos N, Antoniou EA, Nonni A, Kontzoglou K, Mantas D. Targeting Histone Deacetylases in Malignant Melanoma: A Future Therapeutic Agent or Just Great Expectations? Anticancer Res. 2017 Oct;37(10):5355-5362. doi: 10.21873/anticanres.11961. PMID: 28982843. 17: Xu H, Roberts LR, Chou S, Pierce B, Narayanan A, Jones LH. Quantitative measurement of intracellular HDAC1/2 drug occupancy using a trans-cyclooctene largazole thiol probe. Medchemcomm. 2017 Jan 9;8(4):767-770. doi: 10.1039/c6md00633g. PMID: 30108795; PMCID: PMC6072125. 18: Mohseni J, Al-Najjar BO, Wahab HA, Zabidi-Hussin ZA, Sasongko TH. Transcript, methylation and molecular docking analyses of the effects of HDAC inhibitors, SAHA and Dacinostat, on SMN2 expression in fibroblasts of SMA patients. J Hum Genet. 2016 Sep;61(9):823-30. doi: 10.1038/jhg.2016.61. Epub 2016 Jun 2. PMID: 27251006. 19: Kopljar I, Gallacher DJ, De Bondt A, Cougnaud L, Vlaminckx E, Van den Wyngaert I, Lu HR. Functional and Transcriptional Characterization of Histone Deacetylase Inhibitor-Mediated Cardiac Adverse Effects in Human Induced Pluripotent Stem Cell-Derived Cardiomyocytes. Stem Cells Transl Med. 2016 May;5(5):602-12. doi: 10.5966/sctm.2015-0279. Epub 2016 Mar 31. PMID: 27034410; PMCID: PMC4835253. 20: Durlak M, Fugazza C, Elangovan S, Marini MG, Marongiu MF, Moi P, Fraietta I, Cappella P, Barbarani G, Font-Monclus I, Mauri M, Ottolenghi S, Gasparri F, Ronchi A. A Novel High-Content Immunofluorescence Assay as a Tool to Identify at the Single Cell Level γ-Globin Inducing Compounds. PLoS One. 2015 Oct 28;10(10):e0141083. doi: 10.1371/journal.pone.0141083. PMID: 26509275; PMCID: PMC4624791.