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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
Structure of PIMONIDAZOLE

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

HIDE SMILES / InChI
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: thiol-containing proteins specifically in hypoxic cells
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.01 mg × h/L
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
27.925 mg × h/L
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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
Determination of hypoxic region by hypoxia marker in developing mouse embryos in vivo: a possible signal for vessel development.
2001 Feb
Semiquantitative immunohistochemical analysis for hypoxia in human tumors.
2001 Feb 1
Estimation of oxygen distribution in RIF-1 tumors by diffusion model-based interpretation of pimonidazole hypoxia and eppendorf measurements.
2001 Jan
Hypoxia in the thymus: role of oxygen tension in thymocyte survival.
2002 Apr
Pimonidazole binding and tumor vascularity predict for treatment outcome in head and neck cancer.
2002 Dec 1
Orally administered pimonidazole to label hypoxic tumor cells.
2002 Dec 1
HIF-1A, pimonidazole, and iododeoxyuridine to estimate hypoxia and perfusion in human head-and-neck tumors.
2002 Dec 1
Hepatocyte growth factor and c-Met inhibition by hepatic cell hypoxia: a potential mechanism for liver regeneration failure in experimental cirrhosis.
2002 Feb
Local hypoxia is produced at sites of intratumour injection.
2002 Feb 1
The importance of cycling of blood alcohol levels in the pathogenesis of experimental alcoholic liver disease in rats.
2002 Jul
Phase 1 study to identify tumour hypoxia in patients with head and neck cancer using technetium-99m BRU 59-21.
2002 Sep
Tumor hypoxia at the micro-regional level: clinical relevance and predictive value of exogenous and endogenous hypoxic cell markers.
2003 Apr
Tumor oxygen dynamics: correlation of in vivo MRI with histological findings.
2003 Jul-Aug
Mast cell inhibitor cromolyn increases blood clotting and hypoxia in murine breast cancer.
2003 Oct 20
Cellular responses to hypoxia after renal segmental infarction.
2003 Sep
Glucose transporter-1 (GLUT-1): a potential marker of prognosis in rectal carcinoma?
2003 Sep 1
Chronic intragastric alcohol exposure causes hypoxia and oxidative stress in the rat pancreas.
2003 Sep 1
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
Tumor-dependent kinetics of partial pressure of oxygen fluctuations during air and oxygen breathing.
2004 Sep 1
Up-regulation of HIF in experimental acute renal failure: evidence for a protective transcriptional response to hypoxia.
2005 Feb
Expression of the proapoptotic protein Bid is an adverse prognostic factor for radiotherapy outcome in carcinoma of the cervix.
2005 Feb 14
Erythropoietin and erythropoietin receptor expression in head and neck cancer: relationship to tumor hypoxia.
2005 Jan 1
Tirapazamine administered as a neoadjuvant to radiotherapy reduces metastatic dissemination.
2005 Jun 1
Phenytoin teratogenicity: hypoxia marker and effects on embryonic heart rhythm suggest an hERG-related mechanism.
2005 Mar
Patents

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
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.
Name Type Language
PIMONIDAZOLE
INN   WHO-DD  
INN  
Official Name English
Pimonidazole [WHO-DD]
Common Name English
NSC-380540
Code English
pimonidazole [INN]
Common Name English
RO 03-8799
Code English
RO-038799
Code English
RO-03-8799
Code English
1-PIPERIDINEETHANOL, .ALPHA.-((2-NITRO-1H-IMIDAZOL-1-YL)METHYL)-
Systematic Name English
PD 126675
Code English
(±)-.ALPHA.-((2-NITROIMIDAZOL-1-YL)METHYL)-1-PIPERIDINEETHANOL
Systematic Name English
PD-126675
Code English
Classification Tree Code System Code
NCI_THESAURUS C798
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
Code System Code Type Description
DRUG BANK
DB12485
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
MESH
C033815
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
FDA UNII
46JO4D76R2
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
SMS_ID
100000081955
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
ChEMBL
CHEMBL58752
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
NCI_THESAURUS
C1196
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
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EPA CompTox
DTXSID50867867
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
CAS
70132-50-2
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
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PUBCHEM
50981
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
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INN
6126
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
NSC
380540
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY
EVMPD
SUB09846MIG
Created by admin on Fri Dec 15 15:41:38 GMT 2023 , Edited by admin on Fri Dec 15 15:41:38 GMT 2023
PRIMARY