Resminostat HCl | CAS#1187075-34-8 | HDAC1/3/6 inhibitor

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

MedKoo CAT#: 562169

CAS#: 1187075-34-8 (HCl)

Description: Resminostat is an orally bioavailable inhibitor of histone deacetylase 1 (HDAC1), HDAC3, and HDAC6 (IC50s = 43-72 nM),

Chemical Structure

Resminostat HCl

CAS# 1187075-34-8 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562169
Name: Resminostat HCl
CAS#: 1187075-34-8 (HCl)
Chemical Formula: C16H20ClN3O4S
Exact Mass: 0.00
Molecular Weight: 385.860
Elemental Analysis: C, 49.80; H, 5.22; Cl, 9.19; N, 10.89; O, 16.59; S, 8.31

Price and Availability

Size	Price	Availability
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
200mg	USD 1350	2 Weeks
500mg	USD 2850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 1187075-34-8 (HCl) 864814-88-0 (free base)

Synonym: Resminostat Hydrochloride; Resminostat HCl; 4SC-201; 4SC-201; 4SC-201; RAS2410; RAS-2410; RAS 2410;

IUPAC/Chemical Name: (E)-3-[1-[4-[(Dimethylamino)methyl]phenyl]sulfonylpyrrol-3-yl]-N-hydroxyprop-2-enamide;hydrochloride

InChi Key: BVXPKDRKHXARHY-HAAWTFQLSA-N

InChi Code: InChI=1S/C16H19N3O4S.ClH/c1-18(2)11-13-3-6-15(7-4-13)24(22,23)19-10-9-14(12-19)5-8-16(20)17-21;/h3-10,12,21H,11H2,1-2H3,(H,17,20);1H/b8-5+;

SMILES Code: O=C(NO)/C=C/C1=CN(S(=O)(C2=CC=C(CN(C)C)C=C2)=O)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 and DMF

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO and DMF

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:

Product Data:

Product Data

Instruction:

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Biological target:	Resminostat dose-dependently and selectively inhibits HDAC1/3/6 with IC50 of 42.5 nM/50.1 nM/71.8 nM. It is less potent to HDAC8 with IC50 of 877 nM.
In vitro activity:	The combined use of resminostat and gefitinib increased BIMEL protein level in the non-small cell lung cancer cell line PC-9 and induced apoptosis, which led to remarkable shrinkage of tumor. These findings suggest the potential of resminostat to circumvent tolerance to EGFR-TKIs associated with BIM deletion polymorphism. Reference: J Med Invest. 2020;67(3.4):343-350. https://pubmed.ncbi.nlm.nih.gov/33148913/
In vivo activity:	Resminostat plus S-1 therapy did not improve progression-free survival nor overall survival for patients with pre-treated biliary tract cancers. Addition of resminostat to S-1 was associated with higher incidence of treatment-related adverse events. Reference: Cancer Med. 2021 Mar;10(6):2088-2099. https://pubmed.ncbi.nlm.nih.gov/33635605/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	10.0	2.59
	DMF	0.5	0.13

Preparing Stock Solutions

The following data is based on the product molecular weight 385.86 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:	1. Arai S, Takeuchi S, Fukuda K, Tanimoto A, Nishiyama A, Konishi H, Takagi A, Takahashi H, Ong ST, Yano S. Resminostat, a histone deacetylase inhibitor, circumvents tolerance to EGFR inhibitors in EGFR-mutated lung cancer cells with BIM deletion polymorphism. J Med Invest. 2020;67(3.4):343-350. doi: 10.2152/jmi.67.343. PMID: 33148913. 2. Palermo E, Acchioni C, Di Carlo D, Zevini A, Muscolini M, Ferrari M, Castiello L, Virtuoso S, Borsetti A, Antonelli G, Turriziani O, Sgarbanti M, Hiscott J. Activation of Latent HIV-1 T Cell Reservoirs with a Combination of Innate Immune and Epigenetic Regulators. J Virol. 2019 Oct 15;93(21):e01194-19. doi: 10.1128/JVI.01194-19. PMID: 31413127; PMCID: PMC6803272. 3. Ueno M, Morizane C, Furukawa M, Sakai D, Komatsu Y, Nakai Y, Tsuda M, Ozaka M, Mizuno N, Muto M, Fukutomi A, Ikeda M, Tsuji A, Katanuma A, Moriwaki T, Kajiwara T, Ishii H, Negoro Y, Shimizu S, Nemoto N, Kobayashi S, Makino K, Furuse J. A randomized, double-blind, phase II study of oral histone deacetylase inhibitor resminostat plus S-1 versus placebo plus S-1 in biliary tract cancers previously treated with gemcitabine plus platinum-based chemotherapy. Cancer Med. 2021 Mar;10(6):2088-2099. doi: 10.1002/cam4.3813. Epub 2021 Feb 26. PMID: 33635605; PMCID: PMC7957161. 4. Walewski J, Paszkiewicz-Kozik E, Borsaru G, Hellmann A, Janikova A, Warszewska A, Mais A, Ammendola A, Herz T, Krauss B, Henning SW. Resminostat in patients with relapsed or refractory Hodgkin lymphoma: results of the phase II SAPHIRE study. Leuk Lymphoma. 2019 Mar;60(3):675-684. doi: 10.1080/10428194.2018.1492122. Epub 2018 Aug 30. PMID: 30160566.
In vitro protocol:	1. Arai S, Takeuchi S, Fukuda K, Tanimoto A, Nishiyama A, Konishi H, Takagi A, Takahashi H, Ong ST, Yano S. Resminostat, a histone deacetylase inhibitor, circumvents tolerance to EGFR inhibitors in EGFR-mutated lung cancer cells with BIM deletion polymorphism. J Med Invest. 2020;67(3.4):343-350. doi: 10.2152/jmi.67.343. PMID: 33148913. 2. Palermo E, Acchioni C, Di Carlo D, Zevini A, Muscolini M, Ferrari M, Castiello L, Virtuoso S, Borsetti A, Antonelli G, Turriziani O, Sgarbanti M, Hiscott J. Activation of Latent HIV-1 T Cell Reservoirs with a Combination of Innate Immune and Epigenetic Regulators. J Virol. 2019 Oct 15;93(21):e01194-19. doi: 10.1128/JVI.01194-19. PMID: 31413127; PMCID: PMC6803272.
In vivo protocol:	1. Ueno M, Morizane C, Furukawa M, Sakai D, Komatsu Y, Nakai Y, Tsuda M, Ozaka M, Mizuno N, Muto M, Fukutomi A, Ikeda M, Tsuji A, Katanuma A, Moriwaki T, Kajiwara T, Ishii H, Negoro Y, Shimizu S, Nemoto N, Kobayashi S, Makino K, Furuse J. A randomized, double-blind, phase II study of oral histone deacetylase inhibitor resminostat plus S-1 versus placebo plus S-1 in biliary tract cancers previously treated with gemcitabine plus platinum-based chemotherapy. Cancer Med. 2021 Mar;10(6):2088-2099. doi: 10.1002/cam4.3813. Epub 2021 Feb 26. PMID: 33635605; PMCID: PMC7957161. 2. Walewski J, Paszkiewicz-Kozik E, Borsaru G, Hellmann A, Janikova A, Warszewska A, Mais A, Ammendola A, Herz T, Krauss B, Henning SW. Resminostat in patients with relapsed or refractory Hodgkin lymphoma: results of the phase II SAPHIRE study. Leuk Lymphoma. 2019 Mar;60(3):675-684. doi: 10.1080/10428194.2018.1492122. Epub 2018 Aug 30. PMID: 30160566.

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1: Soukupova J, Bertran E, Peñuelas-Haro I, Urdiroz-Urricelqui U, Borgman M, Kohlhof H, Fabregat I. Resminostat induces changes in epithelial plasticity of hepatocellular carcinoma cells and sensitizes them to sorafenib-induced apoptosis. Oncotarget. 2017 Nov 30;8(66):110367-110379. doi: 10.18632/oncotarget.22775. eCollection 2017 Dec 15. PubMed PMID: 29299154; PubMed Central PMCID: PMC5746389.

2: Enzenhofer E, Kadletz L, Stanisz I, Kotowski U, Seemann R, Schmid R, Thurnher D, Heiduschka G. Effect of the histone deacetylase inhibitor resminostat on head and neck squamous cell carcinoma cell lines. Head Neck. 2017 May;39(5):900-907. doi: 10.1002/hed.24699. Epub 2017 Feb 7. PubMed PMID: 28170128.

3: Tambo Y, Hosomi Y, Sakai H, Nogami N, Atagi S, Sasaki Y, Kato T, Takahashi T, Seto T, Maemondo M, Nokihara H, Koyama R, Nakagawa K, Kawaguchi T, Okamura Y, Nakamura O, Nishio M, Tamura T. Phase I/II study of docetaxel combined with resminostat, an oral hydroxamic acid HDAC inhibitor, for advanced non-small cell lung cancer in patients previously treated with platinum-based chemotherapy. Invest New Drugs. 2017 Apr;35(2):217-226. doi: 10.1007/s10637-017-0435-2. Epub 2017 Jan 30. PubMed PMID: 28138828.

4: Ellerhoff TP, Berchtold S, Venturelli S, Burkard M, Smirnow I, Wulff T, Lauer UM. Novel epi-virotherapeutic treatment of pancreatic cancer combining the oral histone deacetylase inhibitor resminostat with oncolytic measles vaccine virus. Int J Oncol. 2016 Nov;49(5):1931-1944. doi: 10.3892/ijo.2016.3675. Epub 2016 Aug 31. PubMed PMID: 27601235.

5: Peng X, Zhang D, Li Z, Fu M, Liu H. mTOR inhibition sensitizes human hepatocellular carcinoma cells to resminostat. Biochem Biophys Res Commun. 2016 Sep 2;477(4):556-562. doi: 10.1016/j.bbrc.2016.06.060. Epub 2016 Jun 14. PubMed PMID: 27311860.

6: Fu M, Shi W, Li Z, Liu H. Activation of mPTP-dependent mitochondrial apoptosis pathway by a novel pan HDAC inhibitor resminostat in hepatocellular carcinoma cells. Biochem Biophys Res Commun. 2016 Sep 2;477(4):527-533. doi: 10.1016/j.bbrc.2016.04.147. Epub 2016 May 1. PubMed PMID: 27144317.

7: Bitzer M, Horger M, Giannini EG, Ganten TM, Wörns MA, Siveke JT, Dollinger MM, Gerken G, Scheulen ME, Wege H, Zagonel V, Cillo U, Trevisani F, Santoro A, Montesarchio V, Malek NP, Holzapfel J, Herz T, Ammendola AS, Pegoraro S, Hauns B, Mais A, Lauer UM, Henning SW, Hentsch B. Resminostat plus sorafenib as second-line therapy of advanced hepatocellular carcinoma - The SHELTER study. J Hepatol. 2016 Aug;65(2):280-8. doi: 10.1016/j.jhep.2016.02.043. Epub 2016 Mar 4. PubMed PMID: 26952006.

8: Zhao J, Lawless MW. Resminostat: Opening the door to epigenetic treatments for liver cancer. Hepatology. 2016 Feb;63(2):668-9. doi: 10.1002/hep.27853. Epub 2015 May 29. PubMed PMID: 25891162.

9: Kitazono S, Fujiwara Y, Nakamichi S, Mizugaki H, Nokihara H, Yamamoto N, Yamada Y, Inukai E, Nakamura O, Tamura T. A phase I study of resminostat in Japanese patients with advanced solid tumors. Cancer Chemother Pharmacol. 2015 Jun;75(6):1155-61. doi: 10.1007/s00280-015-2741-8. Epub 2015 Apr 7. PubMed PMID: 25847480.

10: Ruf B, Berchtold S, Venturelli S, Burkard M, Smirnow I, Prenzel T, Henning SW, Lauer UM. Combination of the oral histone deacetylase inhibitor resminostat with oncolytic measles vaccine virus as a new option for epi-virotherapeutic treatment of hepatocellular carcinoma. Mol Ther Oncolytics. 2015 Oct 7;2:15019. doi: 10.1038/mto.2015.19. eCollection 2015. PubMed PMID: 27119111; PubMed Central PMCID: PMC4782956.

11: Brunetto AT, Ang JE, Lal R, Olmos D, Molife LR, Kristeleit R, Parker A, Casamayor I, Olaleye M, Mais A, Hauns B, Strobel V, Hentsch B, de Bono JS. First-in-human, pharmacokinetic and pharmacodynamic phase I study of Resminostat, an oral histone deacetylase inhibitor, in patients with advanced solid tumors. Clin Cancer Res. 2013 Oct 1;19(19):5494-504. doi: 10.1158/1078-0432.CCR-13-0735. Epub 2013 Sep 24. PubMed PMID: 24065624; PubMed Central PMCID: PMC3790647.

12: 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. 2014;21(23):2642-64. PubMed PMID: 23895688.

13: Wörns MA. Systemic therapy and synergies by combination. Dig Dis. 2013;31(1):104-11. doi: 10.1159/000347202. Epub 2013 Jun 17. Review. PubMed PMID: 23797131.

14: Mandl-Weber S, Meinel FG, Jankowsky R, Oduncu F, Schmidmaier R, Baumann P. The novel inhibitor of histone deacetylase resminostat (RAS2410) inhibits proliferation and induces apoptosis in multiple myeloma (MM) cells. Br J Haematol. 2010 May;149(4):518-28. doi: 10.1111/j.1365-2141.2010.08124.x. Epub 2010 Mar 1. PubMed PMID: 20201941.

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Resminostat HCl featured