Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H23NO4 |
Molecular Weight | 341.4009 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(NC(=O)CC2=CC=C(OC(C)(C)C(O)=O)C=C2)=CC(C)=C1
InChI
InChIKey=BNFRJXLZYUTIII-UHFFFAOYSA-N
InChI=1S/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)
DescriptionCurator's Comment: Description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800008565
Curator's Comment: Description was created based on several sources, including:
http://adisinsight.springer.com/drugs/800008565
Efaproxiral is a synthetic, small molecule, radiation-sensitising agent being developed by Allos Therapeutics primarily for the treatment of cancer. It works by binding and allosterically stabilising deoxyhaemoglobin in hypoxic regions of tumour tissue. This increases oxygen uptake of the tumour tissue and restores its sensitivity to radiation therapy, making therapy potentially more successful. But no benefit was seen for efaproxiral in phase III clinical trials. The only serious adverse effect detected was hypoxaemia. Efaproxiral is explicitly excluded from the 2012 World Anti-Doping Agency list of Prohibited Substances and is explicitly included in the Prohibited Methods section M1 as a forbidden procedure to alter the oxygen-haemoglobin dissociation curve in order to allosterically modify haemoglobin.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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RSR13, a potential athletic performance enhancement agent: detection in urine by gas chromatography/mass spectrometry. | 2001 |
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Effects of enhanced oxygen release from hemoglobin by RSR13 in an acute renal failure model. | 2001 Oct |
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[Blood doping and cardiovascular consequences]. | 2002 Dec 21 |
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The effect of RSR13, a synthetic allosteric modifier of hemoglobin, on brain tissue pO2 (measured by EPR oximetry) following severe hemorrhagic shock in rats. | 2003 |
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The dose-dependent effect of RSR13, a synthetic allosteric modifier of hemoglobin, on physiological parameters and brain tissue oxygenation in rats. | 2003 |
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Effect of RSR13, an allosteric hemoglobin modifier, on oxygenation in murine tumors: an in vivo electron paramagnetic resonance oximetry and bold MRI study. | 2004 Jul 1 |
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Efaproxiral: a novel radiation sensitiser. | 2004 May |
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Modeling of the response of ptO2 in rat brain to changes in physiological parameters. | 2005 |
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Role of efaproxiral in metastatic brain tumors. | 2006 Apr |
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Cerebral metastases--a therapeutic update. | 2006 Aug |
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Efaproxiral red blood cell concentration predicts efficacy in patients with brain metastases. | 2006 Jun 19 |
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Mass spectrometric characterization of efaproxiral (RSR13) and its implementation into doping controls using liquid chromatography-atmospheric pressure ionization-tandem mass spectrometry. | 2006 Mar |
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Reduction in hemoglobin-oxygen affinity results in the improvement of exercise capacity in mice with chronic heart failure. | 2008 Aug 26 |
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Role of palliative radiotherapy in brain metastases. | 2009 Jan |
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The role of emerging and investigational therapies for metastatic brain tumors: a systematic review and evidence-based clinical practice guideline of selected topics. | 2010 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16314619
Efaproxiral was administered intravenously via a central venous access device over 30 minutes; the infusion was completed no more than 30 minutes before whole-brain radiation therapy. The intended daily dose of efaproxiral was 75 or 100 mg/kg.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9822166
EMT6 cells in exponentially growing cell cultures were treated with 300 mg/ml of RSR13 (Efaproxiral), with radiation, or with RSR13 (Efaproxiral) plus irradiation under either aerobic or hypoxic conditions (7.5 Gy for aerobic cultures and 20 Gy for hypoxic cultures). The survival of irradiated EMT6 cells was the same
whether cells were irradiated in the presence or in
the absence of RSR13 (Efaproxiral).
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NCI_THESAURUS |
C798
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WHO-VATC |
QL01XD06
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WHO-ATC |
L01XD06
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FDA ORPHAN DRUG |
158802
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131179-95-8
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SUB21811
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8198
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J81E81G364
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100000088256
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DB08486
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122335
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CHEMBL18901
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EFAPROXIRAL
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C1435
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DTXSID40156934
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m4838
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4465
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OO-16
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)