131179-95-8

Basic information

• Product Name: Efaproxiral
• Synonyms: 2-(4-(((3,5-dimethylanilino)carbonyl)methyl)phenoxy)-2-methylpropionic acid;2-[4-(3,5-Dimethylphenylcarbamoylmethyl)phenoxy]-2-methylpropionic acid;Efaproxiral;Efaproxiral free acid;faproxiral;EFAPROXIRALUM
• CAS NO: 131179-95-8
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.4
• EINECS: 1806241-263-5
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 131179-95-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 48-50°C
• Boiling Point: 554.5 °C at 760 mmHg
• Flash Point: 289.2 °C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 3.93E-13mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.26±0.10(Predicted)
• CAS DataBase Reference: Efaproxiral(CAS DataBase Reference)
• NIST Chemistry Reference: Efaproxiral(131179-95-8)
• EPA Substance Registry System: Efaproxiral(131179-95-8)

Safety Data

• Hazardous Substances Data: 131179-95-8(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Efaproxiral is used as an antineoplastic adjunct (radiosensitizer) for enhancing radiation-induced cytotoxicity in cancer cells grown under hypoxic conditions. It increases radiosensitization and inhibits tumor growth in hypoxic tumor models when administered at specific doses.
Used in Enhancing Oxygen Delivery:
Efaproxiral is used as an allosteric modifier of hemoglobin (HB) to increase the partial pressure of oxygen at which Hb is 50% saturated (p50) and decrease the percent oxyhemoglobin (Hb-O2) saturation at a given partial oxygen pressure (pO2). This modification improves oxygen delivery to tissues, which can be beneficial in various medical conditions where oxygen supply is compromised.
Used in Cardiovascular Applications:
Efaproxiral is used to increase the running capacity of normal mice and mice with left coronary artery (LCA) ligation-induced myocardial infarction (MI) when administered at a specific dose. This application highlights its potential in improving oxygen supply to the heart and enhancing cardiac function in certain conditions.

InChI:InChI=1/C20H23NO4/c1-13-9-14(2)11-16(10-13)21-18(22)12-15-5-7-17(8-6-15)25-20(3,4)19(23)24/h5-11H,12H2,1-4H3,(H,21,22)(H,23,24)

Upstream product

• 1019680-83-1 tert-butyl 2-(4-(2-(3,5-dimethylphenylamino)-2-oxoethyl)phenoxy)-2-methylpropanoate 
• 37859-23-7 2-(p-hydroxyphenyl)acetyl chloride 
• 108-69-0 3,5-dimethylaminoaniline 
• 156-38-7 4-hydroxyphenylacetate 
• 2052-01-9 2-bromo-2-methylpropionic acid 
• 131179-77-6 N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide 
• 67-66-3 chloroform 
• 67-64-1 acetone 

Relevant articles and documents

Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral

A safe, functional-group-tolerant and high-throughput version of the trimethylaluminium mediated amide bond formation reaction has been developed in a microreactor system; rimonabant and efaproxiral were prepared to illustrate the utility of the method. The Royal Society of Chemistry.

Mass spectrometric characterization of efaproxiral (RSR13) and its implementation into doping controls using liquid chromatography-atmospheric pressure ionization-tandem mass spectrometry

Efaproxiral (2-[4-[[(3,5-dimethylanilino)carbonyl]methyl]phenoxyl]-2- methylpropionic acid, formerly referred to as RSR13) is prohibited in sports according to the World Anti-Doping Agency (WADA). The drug as well as structurally related compounds and a stable isotope-labeled derivative have been synthesized to elucidate the fragmentation pathway of efaproxiral, using electrospray ionization (ESI) and tandem mass spectrometry by employing a novel linear ion trap - orbitrap hybrid mass spectrometer - in positive and negative ionization modes. The elimination of 2-methyl acrylic acid (-86 u) has been identified as a major fragmentation process in both charge states. Negative ionization and collision-induced dissociation (CID) caused an additional release of carbon dioxide (-44 u), and positive ionization the loss of formic acid (-46 u). Efaproxiral was incorporated into an existing screening procedure for doping controls using solid-phase extraction (SPE) followed by liquid chromatography-tandem mass spectrometry, enabling a limit of detection of 2.5 ng/ml and interday precisions ranging from 7.9 to 13.0%. Copyright

Selective phenol alkylation: An improved preparation of efaproxiral

An improved, two-step synthesis of efaproxiral, used in breast cancer therapy, is described, utilizing inexpensive commodity chemicals for starting materials. Selective amide formation and O-alkylation in the presence of multireactive functional groups is demonstrated, thus avoiding protection/deprotection steps. Copyright Taylor & Francis Group, LLC.

Allosteric Modifiers of Hemoglobin. 1. Design, Synthesis, Testing, and Structure-Allosteric Activity Relationship of Novel Hemoglobin Oxygen Affinity Decreasing Agents

Three isomeric series of 2-(aryloxy)-2-methylpropionic acids were prepared and studied for their ability to decrease the oxygen affinity of human hemoglobin A.The isomeric aryloxy groups included 4-methyl>phenoxy, 4-(arylacetamido)phenoxy, and 4-methyl>phenoxy.A total of 20 compounds were synthesized and tested.Structure-activity relationships are presented.Several of the new compounds were found to be strong allosteric effectors of hemoglobin.The two most active compounds are 2-methyl>phenoxy>-2-methylpropionic acid and the corresponding 3,5-dimethyl derivative.The latter two compounds have been compared to other known potent allosteric effectors in the same assay and show greater activity.Both compounds also exhibit a right shift in the oxygen equilibrium curve when incubated with whole blood.The new compounds may be of interest in clinical or biological areas that require or would benefit from a reversal of depleted oxygen supply (i.e., ischemia, stroke, tumor radiotherapy, blood storage, blood substitutes, etc.).They are also structurally related to several marketed antilipidemic agents.