Details
Stereochemistry | ACHIRAL |
Molecular Formula | C20H22NO4.Na |
Molecular Weight | 363.3827 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC1=CC(NC(=O)CC2=CC=C(OC(C)(C)C([O-])=O)C=C2)=CC(C)=C1
InChI
InChIKey=SWDPIHPGORBMFR-UHFFFAOYSA-M
InChI=1S/C20H23NO4.Na/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);/q;+1/p-1
Molecular Formula | C20H22NO4 |
Molecular Weight | 340.393 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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Allosteric modification of oxygen delivery by hemoglobin. | 2001 Mar |
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High-resolution crystal structure of deoxy hemoglobin complexed with a potent allosteric effector. | 2001 May |
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Enhancement of tumor oxygenation and radiation response by the allosteric effector of hemoglobin, RSR13. | 2001 Sep |
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[Blood doping and cardiovascular consequences]. | 2002 Dec 21 |
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Increasing P(50) does not improve DO(2CRIT) or systemic VO(2) in severe anemia. | 2002 Jul |
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Survival of patients with newly diagnosed glioblastoma multiforme treated with RSR13 and radiotherapy: results of a phase II new approaches to brain tumor therapy CNS consortium safety and efficacy study. | 2002 Jul 15 |
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Pharmacological correction of hypothermic P(50) shift does not alter outcome from focal cerebral ischemia in rats. | 2002 May |
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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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Allosteric modification of hemoglobin by RSR13 as a therapeutic strategy. | 2003 |
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Efaproxiral (Allos Therapeutics). | 2003 Aug |
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RSR13 plus cranial radiation therapy in patients with brain metastases: comparison with the Radiation Therapy Oncology Group Recursive Partitioning Analysis Brain Metastases Database. | 2003 Jun 15 |
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Novel radiosensitizers for tumors of the central nervous system. | 2004 Dec |
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Effects of RSR13 and oxygen on the cytotoxicity of cisplatin and carboplatin to EMT6 mouse mammary tumor cells in vitro and in vivo. | 2004 Jan |
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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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Effects of a pharmacologically-induced shift of hemoglobin-oxygen dissociation on myocardial energetics during ischemia in patients with coronary artery disease. | 2005 |
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Efaproxiral: GSJ 61, JP 4, KDD 86, RS 4, RSR 13. | 2005 |
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R-state hemoglobin bound to heterotropic effectors: models of the DPG, IHP and RSR13 binding sites. | 2005 Jan 31 |
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Hit to Lead Success Stories--IBC Conference: Effective chemistry strategies for reducing attrition rates and speeding lead compounds into the pipeline. 31 January-1 February 2005, San Diego, CA, USA. | 2005 Mar |
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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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Radiation sensitization with redox modulators: a promising approach. | 2006 Feb 1 |
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Blood doping by cobalt. Should we measure cobalt in athletes? | 2006 Jul 24 |
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Efaproxiral red blood cell concentration predicts efficacy in patients with brain metastases. | 2006 Jun 19 |
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Integration of chemotherapy into current treatment strategies for brain metastases from solid tumors. | 2006 Jun 27 |
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Efaproxiral (RSR13) plus oxygen breathing increases the therapeutic ratio of carboplatin in EMT6 mouse mammary tumors. | 2006 Mar |
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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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Whole-brain radiotherapy with or without efaproxiral for the treatment of brain metastases: Determinants of response and its prognostic value for subsequent survival. | 2006 Mar 15 |
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Current therapeutic approaches in patients with brain metastases. | 2006 Nov |
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Using exposure-response and biomarkers to streamline early drug development. | 2007 |
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The effects of Efaproxyn (efaproxiral) on subcutaneous RIF-1 tumor oxygenation and enhancement of radiotherapy-mediated inhibition of tumor growth in mice. | 2007 Aug |
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Improved survival, quality of life, and quality-adjusted survival in breast cancer patients treated with efaproxiral (Efaproxyn) plus whole-brain radiation therapy for brain metastases. | 2007 Dec |
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Whole brain radiotherapy for brain metastases from breast cancer: estimation of survival using two stratification systems. | 2007 Mar 26 |
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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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Trimethylaluminium mediated amide bond formation in a continuous flow microreactor as key to the synthesis of rimonabant and efaproxiral. | 2008 Mar 7 |
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Quality of life in brain metastases radiation trials: a literature review. | 2008 Oct |
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Neuropsychological testing and biomarkers in the management of brain metastases. | 2008 Sep 17 |
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Role of palliative radiotherapy in brain metastases. | 2009 Jan |
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Whole brain radiotherapy with radiosensitizer for brain metastases. | 2009 Jan 6 |
|
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 |
|
Dose-dense temozolomide regimen for the treatment of brain metastases from melanoma, breast cancer, or lung cancer not amenable to surgery or radiosurgery: a multicenter phase II study. | 2010 Mar |
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:39:17 UTC 2023
by
admin
on
Fri Dec 15 15:39:17 UTC 2023
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Record UNII |
3L83QP52XI
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Record Status |
Validated (UNII)
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NCI_THESAURUS |
C798
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NN-12
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CHEMBL18901
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3L83QP52XI
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170787-99-2
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DTXSID50168942
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2725048
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300000001260
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C72748
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