Pimonidazole
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MedKoo CAT#: 206030

CAS#: 70132-50-2

Description: 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

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Pimonidazole
CAS# 70132-50-2

Theoretical Analysis

MedKoo Cat#: 206030
Name: Pimonidazole
CAS#: 70132-50-2
Chemical Formula: C11H18N4O3
Exact Mass: 254.13789
Molecular Weight: 254.29
Elemental Analysis: C, 51.96; H, 7.13; N, 22.03; O, 18.88

Size Price Shipping out time Quantity
20mg USD 250 2 Weeks
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-03. Prices are subject to change without notice.

Pimonidazole, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

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

Certificate of Analysis:

Safety Data Sheet (SDS):

Handling Instructions:

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.

Select a batch to recalculate based on the batch molecular weight:
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

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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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