Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H18N4O3 |
Molecular Weight | 254.2856 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(CN1C=CN=C1[N+]([O-])=O)CN2CCCCC2
InChI
InChIKey=WVWOOAYQYLJEFD-UHFFFAOYSA-N
InChI=1S/C11H18N4O3/c16-10(8-13-5-2-1-3-6-13)9-14-7-4-12-11(14)15(17)18/h4,7,10,16H,1-3,5-6,8-9H2
Pimonidazole (developed as RO 038799) is a derivative of 2-nitroimidazole, which forms adducts (binds to thiol-containing proteins) only at low oxygen tension. Pimonidazole is a novel nontoxic hypoxia marker for the complementary study of tumor hypoxia and cell proliferation in different types of cancer. The drawback of pimonidazole as a hypoxic marker is that it detects only severe hypoxia.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: thiol-containing proteins specifically in hypoxic cells Sources: https://www.ncbi.nlm.nih.gov/pubmed/9826471 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
AUC
Value | Dose | Co-administered | Analyte | Population |
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4.01 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6519157 |
87 mg single, intravenous dose: 87 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIMONIDAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
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27.925 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6519157 |
460 mg single, intravenous dose: 460 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
PIMONIDAZOLE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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Impact of the tumour bed effect on microenvironment, radiobiological hypoxia and the outcome of fractionated radiotherapy of human FaDu squamous-cell carcinoma growing in the nude mouse. | 2001 Dec |
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Determination of hypoxic region by hypoxia marker in developing mouse embryos in vivo: a possible signal for vessel development. | 2001 Feb |
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Semiquantitative immunohistochemical analysis for hypoxia in human tumors. | 2001 Feb 1 |
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Estimation of oxygen distribution in RIF-1 tumors by diffusion model-based interpretation of pimonidazole hypoxia and eppendorf measurements. | 2001 Jan |
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Hypoxia in the thymus: role of oxygen tension in thymocyte survival. | 2002 Apr |
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Pimonidazole binding and tumor vascularity predict for treatment outcome in head and neck cancer. | 2002 Dec 1 |
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Orally administered pimonidazole to label hypoxic tumor cells. | 2002 Dec 1 |
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HIF-1A, pimonidazole, and iododeoxyuridine to estimate hypoxia and perfusion in human head-and-neck tumors. | 2002 Dec 1 |
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Hepatocyte growth factor and c-Met inhibition by hepatic cell hypoxia: a potential mechanism for liver regeneration failure in experimental cirrhosis. | 2002 Feb |
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Local hypoxia is produced at sites of intratumour injection. | 2002 Feb 1 |
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The importance of cycling of blood alcohol levels in the pathogenesis of experimental alcoholic liver disease in rats. | 2002 Jul |
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Phase 1 study to identify tumour hypoxia in patients with head and neck cancer using technetium-99m BRU 59-21. | 2002 Sep |
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Tumor hypoxia at the micro-regional level: clinical relevance and predictive value of exogenous and endogenous hypoxic cell markers. | 2003 Apr |
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Tumor oxygen dynamics: correlation of in vivo MRI with histological findings. | 2003 Jul-Aug |
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Mast cell inhibitor cromolyn increases blood clotting and hypoxia in murine breast cancer. | 2003 Oct 20 |
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Cellular responses to hypoxia after renal segmental infarction. | 2003 Sep |
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Glucose transporter-1 (GLUT-1): a potential marker of prognosis in rectal carcinoma? | 2003 Sep 1 |
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Chronic intragastric alcohol exposure causes hypoxia and oxidative stress in the rat pancreas. | 2003 Sep 1 |
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Hypoxia-inducible factor 1alpha expression as an intrinsic marker of hypoxia: correlation with tumor oxygen, pimonidazole measurements, and outcome in locally advanced carcinoma of the cervix. | 2004 Dec 15 |
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Tumor-dependent kinetics of partial pressure of oxygen fluctuations during air and oxygen breathing. | 2004 Sep 1 |
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Up-regulation of HIF in experimental acute renal failure: evidence for a protective transcriptional response to hypoxia. | 2005 Feb |
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Expression of the proapoptotic protein Bid is an adverse prognostic factor for radiotherapy outcome in carcinoma of the cervix. | 2005 Feb 14 |
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Erythropoietin and erythropoietin receptor expression in head and neck cancer: relationship to tumor hypoxia. | 2005 Jan 1 |
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Tirapazamine administered as a neoadjuvant to radiotherapy reduces metastatic dissemination. | 2005 Jun 1 |
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Phenytoin teratogenicity: hypoxia marker and effects on embryonic heart rhythm suggest an hERG-related mechanism. | 2005 Mar |
Patents
Sample Use Guides
Ten patients with cervical carcinoma received 0.5 g/m2 pimonidazole intravenously followed by biopsy of the cervical carcinoma the next day. Hypoxic cells were recognized by immunohistochemical detection of pimonidazole using a mouse monoclonal antibody.
(18)F-Fluoroazomycin arabinoside (FAZA) will be administered via intravenous injection at a dose of 5.2 MBq/kg with a minimum dose of 100 MBq (2.7 mCi) and a maximum dose of 600 MBq (16.2 mCi) prior to positron emission tomography (PET) imaging. A single dose of oral pimonidazole capsules at a dose of 0.5 g/m2, will be taken by participants 16-20 hours prior to tumor resection surgery.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21296882
The high demand of mitochondrial respiration during insulin secretion, pancreatic β-cells consume large amounts of oxygen in a short time period. There was examined the effect of insulin secretion on cellular oxygen tension in vitro. It was confirmed that Western blotting of pimonidazole adduct was more sensitive than immunostaining for detection of cellular hypoxia in vitro. In MIN6 cells, a pancreatic β-cell line, pimonidazole adduct formation, and stabilization of hypoxia-inducible factor-1α (HIF-1α) were detected under mildly hypoxic conditions. MIN6 cells and PANC-1 cells were incubated at various oxygen tensions in the presence of pimonidazole (10 μM) for 3 h.
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C798
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)