Efaproxiral

Base Information

• Chemical Name: Efaproxiral
• CAS No.: 131179-95-8
• Molecular Formula: C20H23NO4
• Molecular Weight: 341.407
• Hs Code.: 2924299090
• UNII: J81E81G364
• DSSTox Substance ID: DTXSID40156934
• Nikkaji Number: J374.334I
• Wikipedia: Efaproxiral
• Wikidata: Q5347186
• NCI Thesaurus Code: C1435
• Metabolomics Workbench ID: 151616
• ChEMBL ID: CHEMBL18901
• Mol file: 131179-95-8.mol

Synonyms:2-(4-(2-((3,5-dimethylphenyl)amino)-2-oxoethyl)phenoxy)-2-methylpropanoic acid;2-DACMPP;efaproxiral;RSR 13;RSR 56;RSR-13;RSR-56;RSR13;RSR13 cpd

Chemical Property of Efaproxiral

Chemical Property:

• Vapor Pressure: 3.93E-13mmHg at 25°C
• Melting Point: 48-50°C
• Refractive Index: 1.597
• Boiling Point: 554.5 °C at 760 mmHg
• PKA: 3.26±0.10(Predicted)
• Flash Point: 289.2 °C
• PSA: 75.63000
• Density: 1.202g/cm³
• LogP: 3.79960
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

Efaproxiral ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)NC(=O)CC2=CC=C(C=C2)OC(C)(C)C(=O)O)C
• Recent ClinicalTrials: Combination Chemotherapy, Radiation Therapy, and RSR13 in Treating Patients With Stage III Non-small Cell Lung Cancer
• Recent EU Clinical Trials: A Phase 3 Randomized, Open-label Comparative Study of Standard Whole Brain Radiation Therapy with Supplemental Oxygen, with or without Concurrent RSR13 (efaproxiral), in Women with Brain Metastases from Breast Cancer
• Description: Efaproxiral is an allosteric hemoglobin (Hb) modifier that reduces the affinity of Hb for oxygen, increasing the diffusion of oxygen from blood to tissue. In isolated human whole blood, efaproxiral (1.75 mM) increases the partial pressure of oxygen at which Hb is 50% saturated (p50) from 26.75 to 38.63 mm Hg and decreases the percent oxyhemoglobin (Hb-O2) saturation from 48 to 33.8% at a partial oxygen pressure (pO2) of 26 mm Hg. Efaproxiral (150 mg/kg) increases tumor pO2 from 5.2 to 13.1 mm Hg 30 minutes after administration in a RIF-1 mouse fibrosarcoma flank tumor model. Efaproxiral (100 μM) enhances radiation-induced cytotoxicity in EMT6 mouse breast cancer cells grown under hypoxic conditions and increases radiosensitization and inhibits tumor growth in a hypoxic Lewis lung tumor mouse model when administered at a dose of 100 mg/kg. It also increases the running capacity of normal mice and mice with left coronary artery (LCA) ligation-induced myocardial infarction (MI) when administered at a dose of 150 mg/kg.
• Uses: Allosteric modifier of hemoglobin (HB). Binds in the central water cavity of the Hb molecule causing a conformational change such that bound oxygen is released more readily. Antineoplastic adjunct (radiosensitizer).

Technology Process of Efaproxiral

There total 6 articles about Efaproxiral which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

tert-butyl 2-(4-(2-(3,5-dimethylphenylamino)-2-oxoethyl)phenoxy)-2-methylpropanoate (1019680-83-1) → efaproxiral (131179-95-8)

Guidance literature:

With formic acid; at 90 ℃; for 0.133333h;

DOI:10.1039/b719603b

Reference yield: 84.0%

2-bromo-2-methylpropionic acid (2052-01-9) + N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (131179-77-6) → efaproxiral (131179-95-8)

Guidance literature:

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide; With sodium hydroxide; In butanone; at 50 ℃;

2-bromo-2-methylpropionic acid; In butanone; at 50 ℃;

DOI:10.1080/00397910600636527

Reference yield: 68.0%

chloroform (67-66-3,8013-54-5) + N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide (131179-77-6) + acetone (67-64-1) → efaproxiral (131179-95-8)

Guidance literature:

With sodium hydroxide; for 12h; Ambient temperature;

DOI:10.1021/jm00106a041

upstream raw materials:

chloroform

N-(3,5-dimethylphenyl)-4-hydroxyphenylacetamide

acetone

2-bromo-2-methylpropionic acid

Refernces

• 1、 Thevis, Mario,Krug, Oliver,Schaenzer, Wilhelm. "Mass spectrometric characterization of efaproxiral (RSR13) and its implementation into doping controls using liquid chromatography-atmospheric pressure ionization-tandem mass spectrometry". . p. 332 - 338. Retrieved 2007/10/03.
• 2、 Randad, Ramnarayan S.,Mahran, Mona A.,Mehanna, Ahmed S.,Abraham, Donald J.. "Allosteric Modifiers of Hemoglobin. 1. Design, Synthesis, Testing, and Structure-Allosteric Activity Relationship of Novel Hemoglobin Oxygen Affinity Decreasing Agents". . p. 752 - 757. Retrieved 2007/10/02.