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)
Molecular Formula | C20H23NO4 |
Molecular Weight | 341.4009 |
Charge | 0 |
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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Effects of enhanced oxygen release from hemoglobin by RSR13 in an acute renal failure model. | 2001 Oct |
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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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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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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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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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Efaproxiral: a radiation enhancer used in brain metastases from breast cancer. | 2005 Dec |
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Phase II multicenter study of induction chemotherapy followed by concurrent efaproxiral (RSR13) and thoracic radiotherapy for patients with locally advanced non-small-cell lung cancer. | 2005 Sep 1 |
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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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New hope for old drug in patients with brain metastases. | 2006 Feb |
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Radiation sensitization with redox modulators: a promising approach. | 2006 Feb 1 |
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Phase III study of efaproxiral as an adjunct to whole-brain radiation therapy for brain metastases. | 2006 Jan 1 |
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Efaproxiral: should we hold our breath? | 2006 Jan 1 |
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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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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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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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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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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 |
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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
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admin
on
Edited
Fri Dec 15 16:13:17 UTC 2023
by
admin
on
Fri Dec 15 16:13:17 UTC 2023
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Record UNII |
J81E81G364
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Record Status |
Validated (UNII)
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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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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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