151720-43-3

Basic information

• Product Name: OXAMFLATIN
• Synonyms: 2-Penten-4-ynamide, N-hydroxy-5-[3-[(phenylsulfonyl)amino]phenyl]-, (2E)-;(E)-N-hydroxy-5-(3-(phenylsulfonaMido)phenyl)pent-2-en-4-ynaMide;(2E)-N-Hydroxy-5-[3-[(Phenylsulfonyl)Amino]Phenyl]-2-Penten-4-Ynamide;Oxamflatin (Metacept-3)
• CAS NO: 151720-43-3
• Molecular Formula: C₁₇H₁₄N₂O₄S
• Molecular Weight: 342.36906
• Product Categories: Antitumour;Amines;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 151720-43-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 98-100°C
• Appearance: /solid
• Density: 1.44g/cm³
• Refractive Index: 1.685
• Storage Temp.: 2-8°C
• Solubility: DMSO: 13 mg/mL, soluble
• PKA: 7.75±0.10(Predicted)
• CAS DataBase Reference: OXAMFLATIN(CAS DataBase Reference)
• NIST Chemistry Reference: OXAMFLATIN(151720-43-3)
• EPA Substance Registry System: OXAMFLATIN(151720-43-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 151720-43-3(Hazardous Substances Data)

Usage

Description

OXAMFLATIN, also known as a histone deacetylase inhibitor, is a cell-permeable, aromatic sulfonamide derivative with a hydroxamic acid group. It is characterized by its ability to potently inhibit mammalian histone deacetylases (HDACs) by binding to the active site zinc. This unique property makes OXAMFLATIN a promising compound for various applications in the pharmaceutical and biotechnology industries.

Uses

Used in Pharmaceutical Industry:
OXAMFLATIN is used as a histone deacetylase inhibitor for its ability to modulate gene expression and influence cellular processes. It plays a crucial role in the development of therapies for various diseases, including cancer, by altering the epigenetic landscape of cells and promoting a more favorable environment for treatment.
Used in Cancer Research:
In cancer research, OXAMFLATIN is used as a therapeutic agent for its potential to inhibit the activity of HDACs, which are often overexpressed in cancer cells. By targeting these enzymes, OXAMFLATIN can help in the reactivation of tumor suppressor genes, leading to the suppression of tumor growth and the prevention of cancer progression.
Used in Drug Development:
OXAMFLATIN is also used in the development of novel drugs and drug delivery systems, as its HDAC inhibitory properties can be leveraged to enhance the efficacy of existing chemotherapeutic agents. By combining OXAMFLATIN with conventional drugs, researchers aim to improve treatment outcomes and overcome resistance issues in cancer therapy.
Used in Epigenetic Studies:
In the field of epigenetics, OXAMFLATIN is used as a research tool to study the role of histone deacetylases in gene regulation and cellular function. Its ability to inhibit HDACs allows scientists to investigate the underlying mechanisms of various diseases and explore potential therapeutic strategies targeting epigenetic modifications.
Overall, OXAMFLATIN is a versatile compound with significant potential in the pharmaceutical and biotechnology industries, particularly in the development of novel therapeutics for cancer and other diseases. Its unique properties as a histone deacetylase inhibitor make it a valuable asset in the ongoing quest for more effective and targeted treatments.

Enzyme inhibitor

This anti-tumor agent (FW = 342.38 g/mol; CAS 151720-43-3; Solubility: 13 mg/mL DMSO, methanol, acetonitrile, 10 mg/mL), also known as (2E)- 5-[3-[(phenylsulfonyl)amino]phenyl]-pent-2-en-4-ynohydroxamate, inhibits histone deacetylase. Oxamflatin shows antiproliferative activity in vitro against various mouse and human tumor cell lines, attended by drastic changes in the cell morphology and in vivo antitumor activity against B16 melanoma. Oxamflatin causes an elongated cell shape with filamentous protrusions as well as arrest of the cell cycle at the G1 phase in HeLa cells. These phenotypic changes in HeLa cells were similar to those induced by trichostatin A (TSA), a specific inhibitor of histone deacetylase (HDAC).

InChI:InChI=1/C17H14N2O4S/c20-17(18-21)12-5-4-7-14-8-6-9-15(13-14)19-24(22,23)16-10-2-1-3-11-16/h1-3,5-6,8-13,19,21H,(H,18,20)/b12-5+

Upstream product

• 151720-90-0 (E)-5-(3-Benzenesulfonylamino-phenyl)-pent-2-en-4-ynoic acid 
• 143390-49-2 iodo-3-(tert-butyloxycarbonylamino)benzene 
• 151721-61-8 [3-(3-Oxo-prop-1-ynyl)-phenyl]-carbamic acid tert-butyl ester 
• 151721-60-7 [3-(3-Hydroxy-prop-1-ynyl)-phenyl]-carbamic acid tert-butyl ester 
• 151721-07-2 (E)-5-(3-tert-Butoxycarbonylamino-phenyl)-pent-2-en-4-ynoic acid methyl ester 
• 151720-89-7 (E)-5-(3-Benzenesulfonylamino-phenyl)-pent-2-en-4-ynoic acid methyl ester 

Relevant articles and documents

OCULAR HYPOTENSIVE AGENT COMPRISING COMPOUND CAPABLE OF INHIBITING HISTONE DEACETYLASE AS ACTIVE INGREDIENT

An object of the present invention is to find a novel pharmacological effect of a compound having an HDAC inhibitory effect. The compound having an HDAC inhibitory effect of the invention has an excellent effect of cell morphological change on trabecular meshwork cells and/or effect of intraocular pressure reduction, and is therefore useful as a preventive and/or therapeutic agent for a disease considered to be associated with aqueous humor circulation and/or intraocular pressure, particularly as a preventive and/or therapeutic agent for glaucoma or ocular hypertension.

(2E)-5-[3-[(phenylsulfonyl)amino]phenyl]pent-2-en-4-ynohydroxamic acid and its derivatives as novel and potent inhibitors of ras transformation

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