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MedKoo Cat#: 206030 | Name: Pimonidazole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Pimonidazole, also known as Ro 03-8799 and PD 126675, is a nitroimidazole drug with hypoxic selectivity and radiosensitizing property. Pimonidazole is reduced in hypoxic environments as in tumor cells, thereby it can be used as an hypoxia marker. In hypoxic cells, reduced pimonidazole binds to -SH-containing molecules such as glutathione and proteins, and the resulting complexes accumulated in tissues, thereby sensitizing cells to be more susceptible for radiation treatment.

Chemical Structure

Pimonidazole
Pimonidazole
CAS#70132-50-2

Theoretical Analysis

MedKoo Cat#: 206030

Name: Pimonidazole

CAS#: 70132-50-2

Chemical Formula: C11H18N4O3

Exact Mass: 254.1379

Molecular Weight: 254.29

Elemental Analysis: C, 51.96; H, 7.13; N, 22.03; O, 18.88

Price and Availability

Size Price Availability Quantity
20mg USD 350.00
50mg USD 550.00
100mg USD 875.00
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Related CAS #
No Data
Synonym
PD 126675; Ro 038799; PD126675; Ro038799; PD-126675; Ro-038799; Pimonidazole; NSC 380540.
IUPAC/Chemical Name
1-(2-nitro-1H-imidazol-1-yl)-3-(piperidin-1-yl)propan-2-ol
InChi Key
WVWOOAYQYLJEFD-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OC(CN1CCCCC1)CN2C=CN=C2[N+]([O-])=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
        
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C7M11C30
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Pimonidazole, also known as Ro 03-8799 and PD 126675, is a nitroimidazole drug.
In vitro activity:
In order to test this hypothesis, lymphocytes isolated from the spleens of C3H/HeN mice that had been immunised with pimonidazole-labelled 3152-PRO cells were subcultured and tested for their ability to lyse chromium-51 loaded, pimonidazole-labelled 3152-PRO cells in an in vitro assay. In a parallel study, commercially available, rabbit complement was tested for its ability to lyse pimonidazole-labelled V79-4 cells in the presence of monoclonal antibodies which recognise protein adducts of reductively activated pimonidazole. Complement-mediated cell lysis was measured by means of an MTT assay. Complement-mediated and cell-mediated lysis was observed at pimonidazole concentrations which, in themselves, do not produce cell killing. Reference: Br J Cancer Suppl. 1996 Jul;27:S213-6. https://pubmed.ncbi.nlm.nih.gov/8763883/
In vivo activity:
The purpose of this study was to demonstrate the clinical feasibility of quantitative hypoxia detection with pimonidazole, a novel hypoxia marker, and to correlate hypoxia with S-phase markers of tumor proliferation. Hypoxic cells were recognized by immunohistochemical detection of pimonidazole using a mouse monoclonal antibody. Immunostaining with pimonidazole antibody was observed in 9 of 10 tumors, suggesting that hypoxia is a common occurrence in cervical carcinoma. Quantitatively, tumors that had large numbers of hypoxic cells had the greatest percentage of S-phase cells, but some tumors with smaller amounts of hypoxia also had substantial numbers of S-phase cells. Reference: Gynecol Oncol. 1998 Nov;71(2):270-7. https://pubmed.ncbi.nlm.nih.gov/9826471/
Solvent mg/mL mM comments
Solubility
PBS (pH 7.2) 0.2 0.59
Water 1.0 3.93
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 254.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Chou SC, Flood PM, Raleigh JA. Marking hypoxic cells for complement and cytotoxic T lymphocyte-mediated lysis: using pimonidazole. Br J Cancer Suppl. 1996 Jul;27:S213-6. PMID: 8763883; PMCID: PMC2150013. 2. Masaki Y, Shimizu Y, Yoshioka T, Feng F, Zhao S, Higashino K, Numata Y, Kuge Y. Imaging Mass Spectrometry Revealed the Accumulation Characteristics of the 2-Nitroimidazole-Based Agent "Pimonidazole" in Hypoxia. PLoS One. 2016 Aug 31;11(8):e0161639. doi: 10.1371/journal.pone.0161639. PMID: 27580239; PMCID: PMC5007049. 3. Varia MA, Calkins-Adams DP, Rinker LH, Kennedy AS, Novotny DB, Fowler WC Jr, Raleigh JA. Pimonidazole: a novel hypoxia marker for complementary study of tumor hypoxia and cell proliferation in cervical carcinoma. Gynecol Oncol. 1998 Nov;71(2):270-7. doi: 10.1006/gyno.1998.5163. PMID: 9826471.
In vitro protocol:
1. Chou SC, Flood PM, Raleigh JA. Marking hypoxic cells for complement and cytotoxic T lymphocyte-mediated lysis: using pimonidazole. Br J Cancer Suppl. 1996 Jul;27:S213-6. PMID: 8763883; PMCID: PMC2150013.
In vivo protocol:
1. Masaki Y, Shimizu Y, Yoshioka T, Feng F, Zhao S, Higashino K, Numata Y, Kuge Y. Imaging Mass Spectrometry Revealed the Accumulation Characteristics of the 2-Nitroimidazole-Based Agent "Pimonidazole" in Hypoxia. PLoS One. 2016 Aug 31;11(8):e0161639. doi: 10.1371/journal.pone.0161639. PMID: 27580239; PMCID: PMC5007049. 2. Varia MA, Calkins-Adams DP, Rinker LH, Kennedy AS, Novotny DB, Fowler WC Jr, Raleigh JA. Pimonidazole: a novel hypoxia marker for complementary study of tumor hypoxia and cell proliferation in cervical carcinoma. Gynecol Oncol. 1998 Nov;71(2):270-7. doi: 10.1006/gyno.1998.5163. PMID: 9826471.
1: Masunaga S, Sakurai Y, Tanaka H, Hirayama R, Matsumoto Y, Uzawa A, Suzuki M, Kondo N, Narabayashi M, Maruhashi A, Ono K. Radiosensitivity of pimonidazole-unlabelled intratumour quiescent cell population to γ-rays, accelerated carbon ion beams and boron neutron capture reaction. Br J Radiol. 2013 Jan;86(1021):20120302. doi: 10.1259/bjr.20120302. PubMed PMID: 23255546. 2: Masunaga SI, Sakurai Y, Tanaka H, Suzuki M, Kondo N, Narabayashi M, Maruhashi A, Ono K. Wortmannin efficiently suppresses the recovery from radiation-induced damage in pimonidazole-unlabeled quiescent tumor cell population. J Radiat Res. 2012 Oct 24. [Epub ahead of print] PubMed PMID: 23097299. 3: Kato S, Kimura M, Kageyama K, Tanaka H, Miwa N. Enhanced radiosensitization by liposome-encapsulated pimonidazole for anticancer effects on human melanoma cells. J Nanosci Nanotechnol. 2012 Jun;12(6):4472-7. PubMed PMID: 22905487. 4: Hansen AE, Kristensen AT, Jørgensen JT, McEvoy FJ, Busk M, van der Kogel AJ, Bussink J, Engelholm SA, Kjær A. (64)Cu-ATSM and (18)FDG PET uptake and (64)Cu-ATSM autoradiography in spontaneous canine tumors: comparison with pimonidazole hypoxia immunohistochemistry. Radiat Oncol. 2012 Jun 15;7:89. doi: 10.1186/1748-717X-7-89. PubMed PMID: 22704363; PubMed Central PMCID: PMC3403947. 5: Rademakers SE, Lok J, van der Kogel AJ, Bussink J, Kaanders JH. Metabolic markers in relation to hypoxia; staining patterns and colocalization of pimonidazole, HIF-1α, CAIX, LDH-5, GLUT-1, MCT1 and MCT4. BMC Cancer. 2011 May 12;11:167. doi: 10.1186/1471-2407-11-167. PubMed PMID: 21569415; PubMed Central PMCID: PMC3115911. 6: Donaldson SB, Betts G, Bonington SC, Homer JJ, Slevin NJ, Kershaw LE, Valentine H, West CM, Buckley DL. Perfusion estimated with rapid dynamic contrast-enhanced magnetic resonance imaging correlates inversely with vascular endothelial growth factor expression and pimonidazole staining in head-and-neck cancer: a pilot study. Int J Radiat Oncol Biol Phys. 2011 Nov 15;81(4):1176-83. doi: 10.1016/j.ijrobp.2010.09.039. Epub 2011 May 4. PubMed PMID: 21546171. 7: Herrick AL, Gorodkin R, Jeziorska M, Stratford IJ. Testing for hypoxia in forearm skin of patients with systemic sclerosis, assessed by pimonidazole. J Rheumatol. 2010 Sep;37(9):1968-9. doi: 10.3899/jrheum.100174. PubMed PMID: 20810526. 8: Hoogsteen IJ, Lok J, Marres HA, Takes RP, Rijken PF, van der Kogel AJ, Kaanders JH. Hypoxia in larynx carcinomas assessed by pimonidazole binding and the value of CA-IX and vascularity as surrogate markers of hypoxia. Eur J Cancer. 2009 Nov;45(16):2906-14. doi: 10.1016/j.ejca.2009.07.012. Epub 2009 Aug 19. PubMed PMID: 19699082. 9: Rosenberger C, Rosen S, Paliege A, Heyman SN. Pimonidazole adduct immunohistochemistry in the rat kidney: detection of tissue hypoxia. Methods Mol Biol. 2009;466:161-74. doi: 10.1007/978-1-59745-352-3_12. PubMed PMID: 19148611. 10: Gulliksrud K, Vestvik IK, Galappathi K, Mathiesen B, Rofstad EK. Detection of different hypoxic cell subpopulations in human melanoma xenografts by pimonidazole immunohistochemistry. Radiat Res. 2008 Nov;170(5):638-50. doi: 10.1667/RR1400.1. PubMed PMID: 18959463. 11: Koch CJ. Importance of antibody concentration in the assessment of cellular hypoxia by flow cytometry: EF5 and pimonidazole. Radiat Res. 2008 Jun;169(6):677-88. doi: 10.1667/RR1305.1. PubMed PMID: 18494550. 12: Troost EG, Laverman P, Philippens ME, Lok J, van der Kogel AJ, Oyen WJ, Boerman OC, Kaanders JH, Bussink J. Correlation of [18F]FMISO autoradiography and pimonidazole [corrected] immunohistochemistry in human head and neck carcinoma xenografts. Eur J Nucl Med Mol Imaging. 2008 Oct;35(10):1803-11. doi: 10.1007/s00259-008-0772-7. Epub 2008 Apr 18. Erratum in: Eur J Nucl Med Mol Imaging. 2009 Feb;36(2):331. PubMed PMID: 18421457. 13: Scigliano S, Pinel S, Poussier S, Fouyssac F, Plenat F, Karcher G, Chastagner P. Measurement of hypoxia using invasive oxygen-sensitive electrode, pimonidazole binding and 18F-FDG uptake in anaemic or erythropoietin-treated mice bearing human glioma xenografts. Int J Oncol. 2008 Jan;32(1):69-77. PubMed PMID: 18097544. 14: Westbury CB, Pearson A, Nerurkar A, Reis-Filho JS, Steele D, Peckitt C, Sharp G, Yarnold JR. Hypoxia can be detected in irradiated normal human tissue: a study using the hypoxic marker pimonidazole hydrochloride. Br J Radiol. 2007 Nov;80(959):934-8. Epub 2007 Oct 1. PubMed PMID: 17908818. 15: Terada N, Ohno N, Saitoh S, Ohno S. Immunohistochemical detection of hypoxia in mouse liver tissues treated with pimonidazole using "in vivo cryotechnique". Histochem Cell Biol. 2007 Sep;128(3):253-61. Epub 2007 Aug 7. PubMed PMID: 17680263. 16: Hoskin PJ, Carnell DM, Taylor NJ, Smith RE, Stirling JJ, Daley FM, Saunders MI, Bentzen SM, Collins DJ, d'Arcy JA, Padhani AP. Hypoxia in prostate cancer: correlation of BOLD-MRI with pimonidazole immunohistochemistry-initial observations. Int J Radiat Oncol Biol Phys. 2007 Jul 15;68(4):1065-71. PubMed PMID: 17637389. 17: Gabellieri C, Eykyn TR, Leach MO. Conformational exchange in pimonidazole--a hypoxia marker. Magn Reson Chem. 2007 Aug;45(8):621-3. PubMed PMID: 17559161. 18: Shin KH, Diaz-Gonzalez JA, Russell J, Chen Q, Burgman P, Li XF, Ling CC. Detecting changes in tumor hypoxia with carbonic anhydrase IX and pimonidazole. Cancer Biol Ther. 2007 Jan;6(1):70-5. PubMed PMID: 17172824. 19: Yaromina A, Zips D, Thames HD, Eicheler W, Krause M, Rosner A, Haase M, Petersen C, Raleigh JA, Quennet V, Walenta S, Mueller-Klieser W, Baumann M. Pimonidazole labelling and response to fractionated irradiation of five human squamous cell carcinoma (hSCC) lines in nude mice: the need for a multivariate approach in biomarker studies. Radiother Oncol. 2006 Nov;81(2):122-9. Epub 2006 Sep 7. PubMed PMID: 16956683. 20: Durand RE, Aquino-Parsons C. The fate of hypoxic (pimonidazole-labelled) cells in human cervix tumours undergoing chemo-radiotherapy. Radiother Oncol. 2006 Aug;80(2):138-42. Epub 2006 Aug 17. PubMed PMID: 16916562.

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