U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

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
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
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
Allosteric modification of hemoglobin by RSR13 as a therapeutic strategy.
2003
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
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
Efaproxiral: GSJ 61, JP 4, KDD 86, RS 4, RSR 13.
2005
Cerebral metastases--a therapeutic update.
2006 Aug
Integration of chemotherapy into current treatment strategies for brain metastases from solid tumors.
2006 Jun 27
The effects of Efaproxyn (efaproxiral) on subcutaneous RIF-1 tumor oxygenation and enhancement of radiotherapy-mediated inhibition of tumor growth in mice.
2007 Aug
Whole brain radiotherapy for brain metastases from breast cancer: estimation of survival using two stratification systems.
2007 Mar 26
Role of palliative radiotherapy in brain metastases.
2009 Jan
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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:13:17 GMT 2023
Edited
by admin
on Fri Dec 15 16:13:17 GMT 2023
Record UNII
J81E81G364
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
Related Record Type Details
TARGET->MODULATOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY