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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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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Allosteric modification of hemoglobin by RSR13 as a therapeutic strategy. | 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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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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Efaproxiral: GSJ 61, JP 4, KDD 86, RS 4, RSR 13. | 2005 |
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Cerebral metastases--a therapeutic update. | 2006 Aug |
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Integration of chemotherapy into current treatment strategies for brain metastases from solid tumors. | 2006 Jun 27 |
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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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Whole brain radiotherapy for brain metastases from breast cancer: estimation of survival using two stratification systems. | 2007 Mar 26 |
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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 |
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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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:13:17 GMT 2023
by
admin
on
Fri Dec 15 16:13:17 GMT 2023
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Record UNII |
J81E81G364
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Record Status |
Validated (UNII)
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Record Version |
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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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