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 |
MOL RATIO
1 MOL RATIO (average) |
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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
Doses
AEs
PubMed
Patents
Sample Use Guides
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
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).