Resminostat
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MedKoo CAT#: 205787

CAS#: 864814-88-0 (free base)

Description: Resminostat, also known as 4S-201 and RAS2410, is an orally bioavailable inhibitor of histone deacetylases (HDACs) with potential antineoplastic activity. Resminostat binds to and inhibits HDACs leading to an accumulation of highly acetylated histones. This 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.

Chemical Structure

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Resminostat
CAS# 864814-88-0 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 205787
Name: Resminostat
CAS#: 864814-88-0 (free base)
Chemical Formula: C16H19N3O4S
Exact Mass: 349.11
Molecular Weight: 349.410
Elemental Analysis: C, 55.00; H, 5.48; N, 12.03; O, 18.32; S, 9.18

Price and Availability

Size Price Availability Quantity
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1350 2 Weeks
500mg USD 2650 2 Weeks
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Related CAS #: 1187075-34-8 (HCl)   864814-88-0 (free base)    

Synonym: 4SC201; 4SC-201; 4SC 201; RAS-2410; RAS2410; RAS 2410; Resminostat.

IUPAC/Chemical Name: (E)-3-(1-((4-((dimethylamino)methyl)phenyl)sulfonyl)-1H-pyrrol-3-yl)-N-hydroxyacrylamide.

InChi Key: FECGNJPYVFEKOD-VMPITWQZSA-N

InChi Code: InChI=1S/C16H19N3O4S/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)/b8-5+

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

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 ethanol

Shelf Life: >2 years if stored properly

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

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 70.0 200.34
Ethanol 70.0 200.34

Preparing Stock Solutions

The following data is based on the product molecular weight 349.41 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
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: 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.

2: 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.

3: 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.

4: 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.

5: 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.

6: 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.