Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H10N4O4.H2O |
| Molecular Weight | 232.194 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OCCNC(=O)CN1C=CN=C1[N+]([O-])=O
InChI
InChIKey=VLPRXIRKJZLPHS-UHFFFAOYSA-N
InChI=1S/C7H10N4O4.H2O/c12-4-2-8-6(13)5-10-3-1-9-7(10)11(14)15;/h1,3,12H,2,4-5H2,(H,8,13);1H2
| Molecular Formula | C7H10N4O4 |
| Molecular Weight | 214.1787 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Etanidazole (also known as Radinyl) is a 2-nitroimidazole with radiosensitizing properties. Etanidazole exerts its therapeutic action by depleting glutathione and inhibiting glutathione S-transferase, thus enhancing the anticancer effects of radiation therapy. Etanidazole was tested in Phase III clinical trials in patients with advanced head and neck cancer, however, its development was stopped. A fluorinated etanidazole (EF5) may also be useful as an imaging agent for identification of hypoxic, drug-resistant regions of primary tumors and metastases.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
287 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2522918 |
2 g/m² single, intravenous dose: 2 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ETANIDAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.55 mM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1826961 |
4 g/m² single, intravenous dose: 4 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ETANIDAZOLE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2522918 |
2 g/m² single, intravenous dose: 2 g/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ETANIDAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no [Activation 5.0119 uM] | ||||
| no | ||||
| no | ||||
| no | ||||
| no | ||||
| yes [Inhibition 10 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Phase I/pharmacokinetic/biochemical study of the nitroimadazole hypoxic cell sensitiser SR2508 (etanidazole) in combination with cyclophosphamide. | 1993 Oct |
|
| Combined-modality therapy of esophageal cancer with radiotherapy, etanidazole, and cisplatin-fluorouracil, with or without surgery: neurotoxicity, other toxicities and outcome. | 1994 Jun 15 |
|
| Hypoxia in radiation-induced blood-spinal cord barrier breakdown. | 2001 Apr 15 |
|
| Hypoxia and VEGF mRNA expression in human tumors. | 2001 Nov-Dec |
|
| 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. | 2001 Sep |
|
| Combined prostaglandin and nitric oxide inhibition produces anatomic remodeling and closure of the ductus arteriosus in the premature newborn baboon. | 2001 Sep |
|
| Double-walled microspheres for the sustained release of a highly water soluble drug: characterization and irradiation studies. | 2002 Oct 30 |
|
| A phase I trial of etanidazole and hyperfractionated radiotherapy in children with diffuse brainstem glioma. | 2003 Apr 1 |
|
| Developments in radiotherapy and adjuvant chemotherapy for head and neck cancer. | 2003 Feb |
|
| Utility of 19F MRS detection of the hypoxic cell marker EF5 to assess cellular hypoxia in solid tumors. | 2004 Dec |
|
| Hypoxia is important in the biology and aggression of human glial brain tumors. | 2004 Dec 15 |
|
| In vitro activity of Etanidazole against the protozoan parasite Trypanosoma cruzi. | 2004 Mar |
|
| Comparative measurements of hypoxia in human brain tumors using needle electrodes and EF5 binding. | 2004 Mar 1 |
|
| Acute hypoxia enhances spontaneous lymph node metastasis in an orthotopic murine model of human cervical carcinoma. | 2004 Mar 15 |
|
| HER-2/neu overexpression increases the viable hypoxic cell population within solid tumors without causing changes in tumor vascularization. | 2004 Nov |
|
| Oxygen levels in normal and previously irradiated human skin as assessed by EF5 binding. | 2006 Dec |
|
| EF5 binding and clinical outcome in human soft tissue sarcomas. | 2006 Mar 1 |
|
| Detection of tumour hypoxia: comparison between EF5 adducts and [18F]EF3 uptake on an individual mouse tumour basis. | 2006 May |
|
| 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). | 2008 Apr |
Patents
Sample Use Guides
Etanidazole is given at a dose of 2.0 g/m(2), three
times per week for 5.5 weeks in 17 doses up to a total dose of 34 g/m(2). The drug is dissolved in saline and infused i.v., over 10 to 15 min. Radiotherapy is to begin 30 to 60 min after the start of the Etanidazole infusion.
Route of Administration:
Intravenous
Human leukemia cell lines HL60 and MOLT-4 were treated with 10 mM etanidazole by incubating cells (10(6) ml(-1)) in growth medium at 37 Celsius for 1 h before X-irradiation (15 Gy). The treatment of cells with etanidazole enhanced X-ray-induced apoptosis and the ladder-like DNA fragmentation under the hypoxic conditions.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:58:40 GMT 2023
by
admin
on
Fri Dec 15 17:58:40 GMT 2023
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| Record UNII |
0N3DVR1IMU
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| Record Status |
Validated (UNII)
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| Record Version |
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182323-12-2
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DTXSID00171284
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |