382180-17-8

Basic information

• Product Name: Pyroxamide
• Synonyms: 2-[1-carbaMoyl-N-(2H-pyran-2-yl)forMaMido]-N-hydroxy-N'-(pyridin-3-yl)octanediaMide;PyroxaMide (NSC 696085);N1-Hydroxy-N8-3-pyridinyl-octanediamide;N1-Hydroxy-N8-(pyridin-3-yl)octanediamide;Octanediamide, N1-hydroxy-N8-3-pyridinyl-;N-Hydroxy-N'-3-pyridinyloctanediamide;Pyroxamide
• CAS NO: 382180-17-8
• Molecular Formula: C13H19N3O3
• Molecular Weight: 265.30826
• Mol File: 382180-17-8.mol
• Article Data: 1

Chemical Properties

• Appearance: white to beige/
• Density: 1.215 g/cm³
• Storage Temp.: ?20°C
• Solubility: DMSO: soluble10mg/mL (clear solution)
• CAS DataBase Reference: Pyroxamide(CAS DataBase Reference)
• NIST Chemistry Reference: Pyroxamide(382180-17-8)
• EPA Substance Registry System: Pyroxamide(382180-17-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 382180-17-8(Hazardous Substances Data)

Usage

Description

Pyroxamide is an inhibitor of histone deacetylases (HDACs), including HDAC1 (IC50 = 0.1-0.2 μM). It is a novel class of anti-neoplastic agent that acts by enhancing acetylation of histones, promoting uncoiling of chromatin, and activation of genes implicated in the regulation of cell survival such as proliferation, differentiation, and apoptosis. Pyroxamide is known to potently inhibit affinity purified HDAC1 and also inhibits the growth of tumor cells in vitro and in vivo, inducing p21/WAF1 expression in tumor cells.

Uses

Used in Oncology:
Pyroxamide is used as an anti-neoplastic agent for its ability to inhibit histone deacetylases, leading to the suppression of tumor cell growth and induction of cell death in certain types of cancer cells in culture. It is particularly effective against cancer cells by promoting the acetylation of histones, which in turn affects the regulation of genes involved in cell survival, proliferation, differentiation, and apoptosis.
Used in Cancer Research:
Pyroxamide is used as a research tool for studying the role of histone deacetylases in cancer cell growth and the potential of HDAC inhibitors in the development of novel cancer therapies. Its potent inhibition of HDAC1 and its effects on tumor cells make it a valuable compound for investigating the mechanisms of cancer progression and the development of targeted treatments.
Used in Drug Development:
Pyroxamide is used as a lead compound in the development of new histone deacetylase inhibitors for cancer treatment. Its ability to induce growth suppression and cell death in cancer cells, as well as its specificity for HDAC1, makes it a promising candidate for further optimization and development into a more potent and selective anti-cancer drug.

references

[1]. butler lm, webb y, agus db, et al. inhibition of transformed cell growth and induction of cellular differentiation by pyroxamide, an inhibitor of histone deacetylase. clin cancer res, 2001, 7(4): 962-970.[2]. kutko mc, glick rd, butler lm, et al. histone deacetylase inhibitors induce growth suppression and cell death in human rhabdomyosarcoma in vitro. clin cancer res, 2003, 9(15): 5749-5755.

Upstream product

• 3946-32-5 suberic acid monomethyl ester 
• 405096-07-3 8-oxo-8-(3-pyridinylamino)-octanoic acid methyl ester 

Relevant articles and documents

Inhibitors of human histone deacetylase: Synthesis and enzyme and cellular activity of straight chain hydroxamates

Inhibitors of histone deacetylase (HDAC) have been shown to induce terminal differentiation of human tumor cell lines and to have antitumor effects in vivo. We have prepared analogues of suberoylanilide hydroxamic acid (SAHA) and trichostatin A and have evaluated them in a human HDAC enzyme inhibition assay, a p21waf1 (p21) promoter assay, and in monolayer growth inhibition assays. One compound, 4-(dimethylamino)-N-[7-(hydroxyamino)-7-oxoheptyl]-benzamide, was found to affect the growth of a panel of eight human tumor cell lines differentially.