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22668-01-5,MFCD00156108
Catalog No.:AA00C27S

22668-01-5 | ETANIDAZOLE

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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00C27S
Chemical Name:
ETANIDAZOLE
CAS Number:
22668-01-5
Molecular Formula:
C7H10N4O4
Molecular Weight:
214.1787
MDL Number:
MFCD00156108
SMILES:
[O-][N+](=O)c1nccn1CC(=O)NCCO
NSC Number:
301467
Properties
Computed Properties
 
Complexity:
242  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
15  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
4  
XLogP3:
-1.3  

Literature

Title: A simplified synthesis of the hypoxia imaging agent 2-(2-Nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-[(18)F]pentafluoropropyl)-acetamide ([18F]EF5).

Journal: Nuclear medicine and biology 20121001

Title: PET of hypoxia: current and future perspectives.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20120801

Title: Discovery and optimization of benzotriazine di-N-oxides targeting replicating and nonreplicating Mycobacterium tuberculosis.

Journal: Journal of medicinal chemistry 20120712

Title: Tracer level electrophilic synthesis and pharmacokinetics of the hypoxia tracer [(18)F]EF5.

Journal: Molecular imaging and biology : MIB : the official publication of the Academy of Molecular Imaging 20120401

Title: The 2-nitroimidazole EF5 is a biomarker for oxidoreductases that activate the bioreductive prodrug CEN-209 under hypoxia.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120315

Title: Imaging tumor sensitivity to a bioreductive prodrug: two for the price of one!

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20120315

Title: In regard to Brown et al. (Int J Radiat Oncol Biol Phys 2010;78:323-327).

Journal: International journal of radiation oncology, biology, physics 20110801

Title: Detection of hypoxia by [18F]EF5 in atherosclerotic plaques in mice.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20110501

Title: In vivo profiling of hypoxic gene expression in gliomas using the hypoxia marker EF5 and laser-capture microdissection.

Journal: Cancer research 20110201

Title: Evaluation of the in vivo radiosensitizing activity of etanidazole using tumor-bearing chick embryo.

Journal: Journal of radiation research 20110101

Title: Numerical modeling of fluid flow in solid tumors.

Journal: PloS one 20110101

Title: Novel docetaxel-loaded nanoparticles based on PCL-Tween 80 copolymer for cancer treatment.

Journal: International journal of nanomedicine 20110101

Title: Biodistribution and dosimetry of (18)F-EF5 in cancer patients with preliminary comparison of (18)F-EF5 uptake versus EF5 binding in human glioblastoma.

Journal: European journal of nuclear medicine and molecular imaging 20101101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Stereotactic ablative radiotherapy should be combined with a hypoxic cell radiosensitizer.

Journal: International journal of radiation oncology, biology, physics 20101001

Title: Voltammetry of hypoxic cells radiosensitizer etanidazole radical anion in water.

Journal: Bioelectrochemistry (Amsterdam, Netherlands) 20100601

Title: Inhibitor of DNA binding/differentiation 2 induced by hypoxia promotes synovial fibroblast-dependent osteoclastogenesis.

Journal: Arthritis and rheumatism 20091201

Title: Atrasentan (ABT-627) enhances perfusion and reduces hypoxia in a human tumor xenograft model.

Journal: Cancer biology & therapy 20091001

Title: Immunohistochemical detection of changes in tumor hypoxia.

Journal: International journal of radiation oncology, biology, physics 20090315

Title: A fast radiotherapy paradigm for anal cancer with volumetric modulated arc therapy (VMAT).

Journal: Radiation oncology (London, England) 20090101

Title: A Novel Docetaxel-Loaded Poly (ε-Caprolactone)/Pluronic F68 Nanoparticle Overcoming Multidrug Resistance for Breast Cancer Treatment.

Journal: Nanoscale research letters 20090101

Title: 18F-EF5: a new PET tracer for imaging hypoxia in head and neck cancer.

Journal: Journal of nuclear medicine : official publication, Society of Nuclear Medicine 20081201

Title: Imaging and analytical methods as applied to the evaluation of vasculature and hypoxia in human brain tumors.

Journal: Radiation research 20081201

Title: Noninvasive molecular imaging of hypoxia in human xenografts: comparing hypoxia-induced gene expression with endogenous and exogenous hypoxia markers.

Journal: Cancer research 20081015

Title: Regulation of cell survival and death signals induced by oxidative stress.

Journal: Journal of clinical biochemistry and nutrition 20080901

Title: Changes in tumor hypoxia induced by mild temperature hyperthermia as assessed by dual-tracer immunohistochemistry.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20080801

Title: Design of antiangiogenic hypoxic cell radiosensitizers: 2-nitroimidazoles containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety.

Journal: Bioorganic & medicinal chemistry 20080601

Title: Importance of antibody concentration in the assessment of cellular hypoxia by flow cytometry: EF5 and pimonidazole.

Journal: Radiation research 20080601

Title: Pharmaceutical particle engineering via spray drying.

Journal: Pharmaceutical research 20080501

Title: A phase I-B trial of the radiosensitizer: etanidazole (SR-2508) with radiosurgery for the treatment of recurrent previously irradiated primary brain tumors or brain metastases (RTOG Study 95-02).

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20080401

Title: Hyperbaric oxygen reduces tissue hypoxia and hypoxia-inducible factor-1 alpha expression in focal cerebral ischemia.

Journal: Stroke 20080301

Title: In vivo measurement of the hypoxia marker EF5 in Shionogi tumours using (19)F magnetic resonance spectroscopy.

Journal: International journal of radiation biology 20080301

Title: Imaging of tumor hypoxia to predict treatment sensitivity.

Journal: Current pharmaceutical design 20080101

Title: Patterns and levels of hypoxia in head and neck squamous cell carcinomas and their relationship to patient outcome.

Journal: International journal of radiation oncology, biology, physics 20071115

Title: Radiosensitization of paclitaxel, etanidazole and paclitaxel+etanidazole nanoparticles on hypoxic human tumor cells in vitro.

Journal: Biomaterials 20070901

Title: Radiosensitization by the combination of SR-2508 and paclitaxel in hypoxic human tumor cells in vitro.

Journal: Journal of radiation research 20070501

Title: In situ oxygen utilization in the rat intervertebral disc.

Journal: Journal of anatomy 20070301

Title: Motexafin gadolinium injection for the treatment of brain metastases in patients with non-small cell lung cancer.

Journal: International journal of nanomedicine 20070301

Title: In vivo performance of implantable biodegradable preparations delivering Paclitaxel and Etanidazole for the treatment of glioma.

Journal: Biomaterials 20070201

Title: Identifying and targeting hypoxia in head and neck cancer: a brief overview of current approaches.

Journal: International journal of radiation oncology, biology, physics 20070101

Title: The radiosensitizing effect of doranidazole on human colorectal cancer cells exposed to high doses of irradiation.

Journal: BMC cancer 20070101

Title: Oxygen levels in normal and previously irradiated human skin as assessed by EF5 binding.

Journal: The Journal of investigative dermatology 20061201

Title: New methods for direct delivery of chemotherapy for treating brain tumors.

Journal: The Yale journal of biology and medicine 20061201

Title: Detection of tumour hypoxia: comparison between EF5 adducts and [18F]EF3 uptake on an individual mouse tumour basis.

Journal: European journal of nuclear medicine and molecular imaging 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Immunomodulatory effects of etanercept in an experimental model of spinal cord injury.

Journal: The Journal of pharmacology and experimental therapeutics 20060301

Title: EF5 binding and clinical outcome in human soft tissue sarcomas.

Journal: International journal of radiation oncology, biology, physics 20060301

Title: MCT-4, A511/Basigin and EF5 expression patterns during early chick cardiomyogenesis indicate cardiac cell differentiation occurs in a hypoxic environment.

Journal: Developmental dynamics : an official publication of the American Association of Anatomists 20060101

Title: Significance of hypoxia in malignant glioma. Re: Evans et al. Hypoxia is important in the biology and aggression of human glial brain tumors. Clin Cancer Res 2004;10:8177-84.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050515

Title: Etanidazole in pH-sensitive liposomes: design, characterization and in vitro/in vivo anti-Trypanosoma cruzi activity.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20050418

Title: Stabilization of the retinal vascular network by reciprocal feedback between blood vessels and astrocytes.

Journal: Development (Cambridge, England) 20050401

Title: Hypoxia is important in the biology and aggression of human glial brain tumors.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20041215

Title: Utility of 19F MRS detection of the hypoxic cell marker EF5 to assess cellular hypoxia in solid tumors.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20041201

Title: HER-2/neu overexpression increases the viable hypoxic cell population within solid tumors without causing changes in tumor vascularization.

Journal: Molecular cancer research : MCR 20041101

Title: Hypoxia and Photofrin uptake in the intraperitoneal carcinomatosis and sarcomatosis of photodynamic therapy patients.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20040715

Title: In vivo evaluation of [18F]fluoroetanidazole as a new marker for imaging tumour hypoxia with positron emission tomography.

Journal: British journal of cancer 20040601

Title: Role of myocardial hypoxia in the remodeling of the embryonic avian cardiac outflow tract.

Journal: Developmental biology 20040315

Title: Acute hypoxia enhances spontaneous lymph node metastasis in an orthotopic murine model of human cervical carcinoma.

Journal: Cancer research 20040315

Title: Comparative measurements of hypoxia in human brain tumors using needle electrodes and EF5 binding.

Journal: Cancer research 20040301

Title: In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi.

Journal: Memorias do Instituto Oswaldo Cruz 20040301

Title: Quality of life of men treated with brachytherapies for prostate cancer.

Journal: Health and quality of life outcomes 20040101

Title: Computer simulation of the delivery of etanidazole to brain tumor from PLGA wafers: comparison between linear and double burst release systems.

Journal: Biotechnology and bioengineering 20030505

Title: Sustained release system for highly water-soluble radiosensitizer drug etanidazole: irradiation and degradation studies.

Journal: Biomaterials 20030501

Title: A phase I trial of etanidazole and hyperfractionated radiotherapy in children with diffuse brainstem glioma.

Journal: International journal of radiation oncology, biology, physics 20030401

Title: Simulation of intratumoral release of Etanidazole: effects of the size of surgical opening.

Journal: Journal of pharmaceutical sciences 20030401

Title: In vivo colocalization of 2-nitroimidazole EF5 fluorescence intensity and electron paramagnetic resonance oximetry in mouse tumors.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20030401

Title: Noninvasive imaging of tumor hypoxia in rats using the 2-nitroimidazole 18F-EF5.

Journal: European journal of nuclear medicine and molecular imaging 20030201

Title: Developments in radiotherapy and adjuvant chemotherapy for head and neck cancer.

Journal: Clinical otolaryngology and allied sciences 20030201

Title: A novel hypoxia-dependent 2-nitroimidazole KIN-841 inhibits tumour-specific angiogenesis by blocking production of angiogenic factors.

Journal: British journal of cancer 20030127

Title: Non-invasive PET and SPECT imaging of tissue hypoxia using isotopically labeled 2-nitroimidazoles.

Journal: Advances in experimental medicine and biology 20030101

Title: Etanidazole-loaded microspheres fabricated by spray-drying different poly(lactide/glycolide) polymers: effects on microsphere properties.

Journal: Journal of biomaterials science. Polymer edition 20030101

Title: Double-walled microspheres for the sustained release of a highly water soluble drug: characterization and irradiation studies.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20021030

Title: Activation of hypoxia-inducible factor-1 in the rat cerebral cortex after transient global ischemia: potential role of insulin-like growth factor-1.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20021015

Title: PEG modulated release of etanidazole from implantable PLGA/PDLA discs.

Journal: Biomaterials 20020901

Title: Effects of hyperglycemia on oxygenation, radiosensitivity and bioenergetic status of subcutaneous RIF-1 tumors.

Journal: International journal of oncology 20020701

Title: Sustained release of etanidazole from spray dried microspheres prepared by non-halogenated solvents.

Journal: Journal of controlled release : official journal of the Controlled Release Society 20020617

Title: Zonal image analysis of tumour vascular perfusion, hypoxia, and necrosis.

Journal: British journal of cancer 20020605

Title: Hypoxia and etanidazole alter radiation-induced apoptosis in HL60 cells but not in MOLT-4 cells.

Journal: International journal of radiation biology 20020401

Title: Vasa vasorum hypoperfusion is responsible for medial hypoxia and anatomic remodeling in the newborn lamb ductus arteriosus.

Journal: Pediatric research 20020201

Title: Dose-intensive therapy for extensive-stage small cell lung cancer and extrapulmonary small cell carcinoma: long-term outcome.

Journal: Biology of blood and marrow transplantation : journal of the American Society for Blood and Marrow Transplantation 20020101

Title: Measurement of absolute oxygen levels in cells and tissues using oxygen sensors and 2-nitroimidazole EF5.

Journal: Methods in enzymology 20020101

Title: Effects of fabrication conditions on the characteristics of etanidazole spray-dried microspheres.

Journal: Journal of microencapsulation 20020101

Title: Hypoxia and VEGF mRNA expression in human tumors.

Journal: Neoplasia (New York, N.Y.) 20011101

Title: Green fluorescent protein is a suitable reporter of tumor hypoxia despite an oxygen requirement for chromophore formation.

Journal: Neoplasia (New York, N.Y.) 20011101

Title: Hypoxia-inducible factor-1alpha is an intrinsic marker for hypoxia in cervical cancer xenografts.

Journal: Cancer research 20011015

Title: Characterization of the effects of antiangiogenic agents on tumor pathophysiology.

Journal: American journal of clinical oncology 20011001

Title: Hypoxic heterogeneity in human tumors: EF5 binding, vasculature, necrosis, and proliferation.

Journal: American journal of clinical oncology 20011001

Title: Intravascular HBO(2) saturations, perfusion and hypoxia in spontaneous and transplanted tumor models.

Journal: International journal of cancer 20010901

Title: Combined prostaglandin and nitric oxide inhibition produces anatomic remodeling and closure of the ductus arteriosus in the premature newborn baboon.

Journal: Pediatric research 20010901

Title: Pharmacokinetics of EF5 [2-(2-nitro-1-H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl) acetamide] in human patients: implications for hypoxia measurements in vivo by 2-nitroimidazoles.

Journal: Cancer chemotherapy and pharmacology 20010901

Title: Validation of the RTOG recursive partitioning classification for head and neck tumors.

Journal: Head & neck 20010801

Title: Differential effects of buthionine sulphoximine in hypoxic and non-hypoxic regions of human cervical carcinoma xenografts.

Journal: Radiotherapy and oncology : journal of the European Society for Therapeutic Radiology and Oncology 20010701

Title: Hypoxia in radiation-induced blood-spinal cord barrier breakdown.

Journal: Cancer research 20010415

Title: Influence of hydralazine administration on oxygenation in spontaneous and transplanted tumor models.

Journal: International journal of radiation oncology, biology, physics 20010301

Title: Hypoxia in human intraperitoneal and extremity sarcomas.

Journal: International journal of radiation oncology, biology, physics 20010201

Title: Effects of radiation on tumor intravascular oxygenation, vascular configuration, development of hypoxia, and clonogenic survival.

Journal: Radiation research 20010201

Title: [18F]-EF5, a marker for PET detection of hypoxia: synthesis of precursor and a new fluorination procedure.

Journal: Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine 20010101

Title: Pneumocystis carinii is resistant to imidazole antifungal agents.

Journal: Antimicrobial agents and chemotherapy 19940801

Title: Combined-modality therapy of esophageal cancer with radiotherapy, etanidazole, and cisplatin-fluorouracil, with or without surgery: neurotoxicity, other toxicities and outcome.

Journal: International journal of radiation oncology, biology, physics 19940615

Title: Phase I/pharmacokinetic/biochemical study of the nitroimadazole hypoxic cell sensitiser SR2508 (etanidazole) in combination with cyclophosphamide.

Journal: British journal of cancer 19931001

Title: Enhancement in the aerobic toxicity of misonidazole and SR-2508 by buthionine sulfoximine and 4-hydroxypyrazole: the role of hydrogen peroxide.

Journal: International journal of radiation oncology, biology, physics 19860701

Title: Oncogenic transformation systems involving mammalian cells in vitro to determine the relative risks of different treatment modalities.

Journal: Strahlentherapie 19841201

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