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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

Molecular Formula C11H18N4O3
Molecular Weight 254.2856
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Inhibition of mitochondrial respiration elevates oxygen concentration but leaves regulation of hypoxia-inducible factor (HIF) intact.
2005-10-01
Comparison of different methods of CAIX quantification in relation to hypoxia in three human head and neck tumor lines.
2005-08
Ischemia-induced cleavage of cadherins in NRK cells: evidence for a role of metalloproteinases.
2005-08
Correction of anaemia through the use of darbepoetin alfa improves chemotherapeutic outcome in a murine model of Lewis lung carcinoma.
2005-07-25
Hypoxic cell turnover in different solid tumor lines.
2005-07-15
Observation of incipient tumor angiogenesis that is independent of hypoxia and hypoxia inducible factor-1 activation.
2005-07-01
Tirapazamine administered as a neoadjuvant to radiotherapy reduces metastatic dissemination.
2005-06-01
Dependence of FDG uptake on tumor microenvironment.
2005-06-01
Role of the hypoxic bone marrow microenvironment in 5T2MM murine myeloma tumor progression.
2005-06
Hypoxia-regulated glucose transporter Glut-1 may influence chemosensitivity to some alkylating agents: results of EORTC (First Translational Award) study of the relevance of tumour hypoxia to the outcome of chemotherapy in human tumour-derived xenografts.
2005-06
A kinetic model for dynamic [18F]-Fmiso PET data to analyse tumour hypoxia.
2005-05-21
Interleukin-12 has no effect on vascular density, perfusion, hypoxia and proliferation of an implanted human squamous cell carcinoma xenograft tumour despite up-regulation of ICAM-1.
2005-05-05
Assessment of regional tumor hypoxia using 18F-fluoromisonidazole and 64Cu(II)-diacetyl-bis(N4-methylthiosemicarbazone) positron emission tomography: Comparative study featuring microPET imaging, Po2 probe measurement, autoradiography, and fluorescent microscopy in the R3327-AT and FaDu rat tumor models.
2005-04-01
The tumor bed effect: increased metastatic dissemination from hypoxia-induced up-regulation of metastasis-promoting gene products.
2005-03-15
Real-time imaging of hypoxia-inducible factor-1 activity in tumor xenografts.
2005-03
Phenytoin teratogenicity: hypoxia marker and effects on embryonic heart rhythm suggest an hERG-related mechanism.
2005-03
Expression of the proapoptotic protein Bid is an adverse prognostic factor for radiotherapy outcome in carcinoma of the cervix.
2005-02-14
Inhibition of tumor necrosis factor-alpha improves physiological angiogenesis and reduces pathological neovascularization in ischemic retinopathy.
2005-02
Up-regulation of HIF in experimental acute renal failure: evidence for a protective transcriptional response to hypoxia.
2005-02
Erythropoietin and erythropoietin receptor expression in head and neck cancer: relationship to tumor hypoxia.
2005-01-01
Mechanism of hypertensive nephropathy in the Dahl/Rapp rat: a primary disorder of vascular smooth muscle.
2005-01
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.
2004-12-15
Lack of microvessels in well-differentiated regions of human head and neck squamous cell carcinoma A253 associated with functional magnetic resonance imaging detectable hypoxia, limited drug delivery, and resistance to irinotecan therapy.
2004-12-01
Evaluation of hypoxia in an experimental rat tumour model by [(18)F]fluoromisonidazole PET and immunohistochemistry.
2004-11-29
Identification of differentially expressed genes in a renal cell carcinoma tumor model after endostatin-treatment.
2004-11
Microregional effects of gemcitabine in HCT-116 xenografts.
2004-09-15
Quantifying transient hypoxia in human tumor xenografts by flow cytometry.
2004-09-01
Tumor-dependent kinetics of partial pressure of oxygen fluctuations during air and oxygen breathing.
2004-09-01
Effects of nicotinamide and carbogen in different murine colon carcinomas: immunohistochemical analysis of vascular architecture and microenvironmental parameters.
2004-09-01
The immunohistochemical assessment of hypoxia, vascularity and proliferation in bladder carcinoma.
2004-08
Tumor hypoxia correlates with metastatic tumor growth of pancreatic cancer in an orthotopic murine model.
2004-08
Overexpression of dimethylarginine dimethylaminohydrolase enhances tumor hypoxia: an insight into the relationship of hypoxia and angiogenesis in vivo.
2004-07-17
In vivo evaluation of [18F]fluoroetanidazole as a new marker for imaging tumour hypoxia with positron emission tomography.
2004-06-01
Hypoperfusion of peritubular capillaries induces chronic hypoxia before progression of tubulointerstitial injury in a progressive model of rat glomerulonephritis.
2004-06
Improved immunohistochemical method for detecting hypoxia gradients in mouse tissues and tumors.
2004-06
Evidence of tubular hypoxia in the early phase in the remnant kidney model.
2004-05
TNP-470 promotes initial vascular sprouting in xenograft tumors.
2004-03
Evidence that involucrin, a marker for differentiation, is oxygen regulated in human squamous cell carcinomas.
2004-02-09
Neuroblastoma survival and death: an in vitro model of hypoxia and metabolic stress.
2004-02
Expression of the pro-angiogenic factors vascular endothelial growth factor and interleukin-8/CXCL8 by human breast carcinomas is responsive to nutrient deprivation and endoplasmic reticulum stress.
2004-01-22
Increased metastatic dissemination in human melanoma xenografts after subcurative radiation treatment: radiation-induced increase in fraction of hypoxic cells and hypoxia-induced up-regulation of urokinase-type plasminogen activator receptor.
2004-01-01
Differentiation-associated staining with anti-pimonidazole antibodies in head and neck tumors.
2004-01
Analysis of the regional uptake of radiolabeled deoxyglucose analogs in human tumor xenografts.
2004-01
Teratogenicity by the hERG potassium channel blocking drug almokalant: use of hypoxia marker gives evidence for a hypoxia-related mechanism mediated via embryonic arrhythmia.
2003-12-01
Endogenous markers of tumor hypoxia predictors of clinical radiation resistance?
2003-12
The effect of elevated intraocular oxygen on organelle degradation in the embryonic chicken lens.
2003-12
Hypoxia and differentiation in squamous cell carcinomas of the uterine cervix: pimonidazole and involucrin.
2003-10-15
GLUT1 and CAIX as intrinsic markers of hypoxia in bladder cancer: relationship with vascularity and proliferation as predictors of outcome of ARCON.
2003-10-06
Tumor oxygen dynamics: correlation of in vivo MRI with histological findings.
2003-09-27
Proliferation and micromilieu during fractionated irradiation of human FaDu squamous cell carcinoma in nude mice.
2003-07
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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:05:44 GMT 2025
Edited
by admin
on Mon Mar 31 18:05:44 GMT 2025
Record UNII
46JO4D76R2
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-380540
Preferred Name English
PIMONIDAZOLE
INN   WHO-DD  
INN  
Official Name English
Pimonidazole [WHO-DD]
Common Name 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 Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
Code System Code Type Description
DRUG BANK
DB12485
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
MESH
C033815
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
FDA UNII
46JO4D76R2
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
SMS_ID
100000081955
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
ChEMBL
CHEMBL58752
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
NCI_THESAURUS
C1196
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID50867867
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
CAS
70132-50-2
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
PUBCHEM
50981
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
INN
6126
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
NSC
380540
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
EVMPD
SUB09846MIG
Created by admin on Mon Mar 31 18:05:44 GMT 2025 , Edited by admin on Mon Mar 31 18:05:44 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
ENANTIOMER -> RACEMATE
ENANTIOMER -> RACEMATE
Related Record Type Details
ACTIVE MOIETY