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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
Structure of EFAPROXIRAL

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)

HIDE SMILES / InChI

Description
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
RSR13, a potential athletic performance enhancement agent: detection in urine by gas chromatography/mass spectrometry.
2001
Effects of enhanced oxygen release from hemoglobin by RSR13 in an acute renal failure model.
2001 Oct
[Blood doping and cardiovascular consequences].
2002 Dec 21
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
The dose-dependent effect of RSR13, a synthetic allosteric modifier of hemoglobin, on physiological parameters and brain tissue oxygenation in rats.
2003
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
Efaproxiral: a novel radiation sensitiser.
2004 May
Modeling of the response of ptO2 in rat brain to changes in physiological parameters.
2005
Role of efaproxiral in metastatic brain tumors.
2006 Apr
Cerebral metastases--a therapeutic update.
2006 Aug
Efaproxiral red blood cell concentration predicts efficacy in patients with brain metastases.
2006 Jun 19
Mass spectrometric characterization of efaproxiral (RSR13) and its implementation into doping controls using liquid chromatography-atmospheric pressure ionization-tandem mass spectrometry.
2006 Mar
Reduction in hemoglobin-oxygen affinity results in the improvement of exercise capacity in mice with chronic heart failure.
2008 Aug 26
Role of palliative radiotherapy in brain metastases.
2009 Jan
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

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
In Vitro Use Guide
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).
Name Type Language
EFAPROXIRAL
INN   MART.   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
EFAPROXIRAL [USAN]
Common Name English
Efaproxiral [WHO-DD]
Common Name English
EFAPROXIRAL [MI]
Common Name English
efaproxiral [INN]
Common Name English
RSR-13
Code English
EFAPROXIRAL [MART.]
Common Name English
RSR13
Code English
PROPANOIC ACID, 2-(4-(2-((3,5-DIMETHYLPHENYL)AMINO)-2-OXOETHYL)PHENOXY)-2-METHYL-
Common Name English
EFAPROXIRAL [VANDF]
Common Name English
2-[4-[(3,5-Dimethylphenyl)amino]-2-oxoethyl]phenoxy]-2-methylpropanic acid
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C798
Created by admin on Fri Dec 15 16:13:18 GMT 2023 , Edited by admin on Fri Dec 15 16:13:18 GMT 2023
WHO-VATC QL01XD06
Created by admin on Fri Dec 15 16:13:18 GMT 2023 , Edited by admin on Fri Dec 15 16:13:18 GMT 2023
WHO-ATC L01XD06
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
FDA ORPHAN DRUG 158802
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
Code System Code Type Description
CAS
131179-95-8
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
PRIMARY
EVMPD
SUB21811
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
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INN
8198
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
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FDA UNII
J81E81G364
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
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SMS_ID
100000088256
Created by admin on Fri Dec 15 16:13:18 GMT 2023 , Edited by admin on Fri Dec 15 16:13:18 GMT 2023
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DRUG BANK
DB08486
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
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PUBCHEM
122335
Created by admin on Fri Dec 15 16:13:18 GMT 2023 , Edited by admin on Fri Dec 15 16:13:18 GMT 2023
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ChEMBL
CHEMBL18901
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
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WIKIPEDIA
EFAPROXIRAL
Created by admin on Fri Dec 15 16:13:18 GMT 2023 , Edited by admin on Fri Dec 15 16:13:18 GMT 2023
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NCI_THESAURUS
C1435
Created by admin on Fri Dec 15 16:13:18 GMT 2023 , Edited by admin on Fri Dec 15 16:13:18 GMT 2023
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EPA CompTox
DTXSID40156934
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
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MERCK INDEX
m4838
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
4465
Created by admin on Fri Dec 15 16:13:17 GMT 2023 , Edited by admin on Fri Dec 15 16:13:17 GMT 2023
PRIMARY
USAN
OO-16
Created by admin on Fri Dec 15 16:13:18 GMT 2023 , Edited by admin on Fri Dec 15 16:13:18 GMT 2023
PRIMARY