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MedKoo Cat#: 592549 | Name: Pimonidazole hydrochloride
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Description:

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

Pimonidazole hydrochloride is a Radiation-Sensitizing Agent.

Chemical Structure

Pimonidazole hydrochloride
Pimonidazole hydrochloride
CAS#70132-51-3

Theoretical Analysis

MedKoo Cat#: 592549

Name: Pimonidazole hydrochloride

CAS#: 70132-51-3

Chemical Formula: C11H19ClN4O3

Exact Mass: 290.1146

Molecular Weight: 290.75

Elemental Analysis: C, 45.44; H, 6.59; Cl, 12.19; N, 19.27; O, 16.51

Price and Availability

Size Price Availability Quantity
10mg USD 500.00
50mg USD 980.00
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Related CAS #
No Data
Synonym
Ro 03-8799; Pimonidazole hydrochloride
IUPAC/Chemical Name
1-Piperidineethanol, alpha-((2-nitro-1H-imidazol-1-yl)methyl)-, monohydrochloride
InChi Key
SKUVJFHTKRTQQZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H18N4O3.ClH/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;1H
SMILES Code
OC(CN1C=CN=C1[N+]([O-])=O)CN2CCCCC2.[H]Cl
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pimonidazole hydrochloride is a Radiation-Sensitizing Agent.
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
DMSO 250.0 859.85
Water 5.0 17.20
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 290.75 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: Oza HH, Ng E, Gilkes DM. Staining Hypoxic Areas of Frozen and FFPE Tissue Sections with Hypoxyprobe™. Methods Mol Biol. 2024;2755:149-163. doi: 10.1007/978-1-0716-3633-6_11. PMID: 38319576. 2: Arvola O, Griffiths B, Rao A, Xu L, Pastroudis IA, Stary CM. Expression of miR-200c corresponds with increased reactive oxygen species and hypoxia markers after transient focal ischemia in mice. Neurochem Int. 2021 Oct;149:105146. doi: 10.1016/j.neuint.2021.105146. Epub 2021 Jul 31. PMID: 34343653; PMCID: PMC8387456. 3: Wu D, Cao W, Xiang D, Hu YP, Luo B, Chen P. Exercise induces tissue hypoxia and HIF-1α redistribution in the small intestine. J Sport Health Sci. 2020 Jan;9(1):82-89. doi: 10.1016/j.jshs.2019.05.002. Epub 2019 May 9. PMID: 31921483; PMCID: PMC6943782. 4: Özen I, Roth M, Barbariga M, Gaceb A, Deierborg T, Genové G, Paul G. Loss of Regulator of G-Protein Signaling 5 Leads to Neurovascular Protection in Stroke. Stroke. 2018 Sep;49(9):2182-2190. doi: 10.1161/STROKEAHA.118.020124. PMID: 30354999; PMCID: PMC6116795. 5: Yu J, Liang F, Huang H, Pirttiniemi P, Yu D. Effects of loading on chondrocyte hypoxia, HIF-1α and VEGF in the mandibular condylar cartilage of young rats. Orthod Craniofac Res. 2018 Feb;21(1):41-47. doi: 10.1111/ocr.12212. Epub 2017 Dec 22. PMID: 29271061. 6: Ebneter A, Kokona D, Schneider N, Zinkernagel MS. Microglia Activation and Recruitment of Circulating Macrophages During Ischemic Experimental Branch Retinal Vein Occlusion. Invest Ophthalmol Vis Sci. 2017 Feb 1;58(2):944-953. doi: 10.1167/iovs.16-20474. PMID: 28170538. 7: Jazwa A, Florczyk U, Grochot-Przeczek A, Krist B, Loboda A, Jozkowicz A, Dulak J. Limb ischemia and vessel regeneration: Is there a role for VEGF? Vascul Pharmacol. 2016 Nov;86:18-30. doi: 10.1016/j.vph.2016.09.003. Epub 2016 Sep 10. PMID: 27620809. 8: Somers E, Lees RD, Hoban K, Sleigh JN, Zhou H, Muntoni F, Talbot K, Gillingwater TH, Parson SH. Vascular Defects and Spinal Cord Hypoxia in Spinal Muscular Atrophy. Ann Neurol. 2016 Feb;79(2):217-30. doi: 10.1002/ana.24549. Epub 2016 Jan 13. PMID: 26506088. 9: Ogino A, Takemura G, Hashimoto A, Kanamori H, Okada H, Nakagawa M, Tsujimoto A, Goto K, Kawasaki M, Nagashima K, Miyakoda G, Fujiwara T, Yabuuchi Y, Fujiwara H, Minatoguchi S. OPC-28326, a selective peripheral vasodilator with angiogenic activity, mitigates postinfarction cardiac remodeling. Am J Physiol Heart Circ Physiol. 2015 Jul 1;309(1):H213-21. doi: 10.1152/ajpheart.00062.2015. Epub 2015 Apr 24. PMID: 25910803. 10: Matsuura Y, Yamashita A, Iwakiri T, Sugita C, Okuyama N, Kitamura K, Asada Y. Vascular wall hypoxia promotes arterial thrombus formation via augmentation of vascular thrombogenicity. Thromb Haemost. 2015 Jul;114(1):158-72. doi: 10.1160/TH14-09-0794. Epub 2015 Apr 2. PMID: 25833755. 11: Caria CR, Moscato CH, Tomé RB, Pedrazzoli J Jr, Ribeiro ML, Gambero A. Nitric oxide interferes with hypoxia signaling during colonic inflammation. Arq Gastroenterol. 2014 Oct-Dec;51(4):302-8. doi: 10.1590/S0004-28032014000400007. PMID: 25591158. 12: Aguilera KY, Brekken RA. Hypoxia Studies with Pimonidazole in vivo. Bio Protoc. 2014 Oct 5;4(19):e1254. doi: 10.21769/bioprotoc.1254. PMID: 27453908; PMCID: PMC4956402. 13: Tawfik A, Markand S, Al-Shabrawey M, Mayo JN, Reynolds J, Bearden SE, Ganapathy V, Smith SB. Alterations of retinal vasculature in cystathionine-β- synthase heterozygous mice: a model of mild to moderate hyperhomocysteinemia. Am J Pathol. 2014 Sep;184(9):2573-85. doi: 10.1016/j.ajpath.2014.05.018. Epub 2014 Jul 10. PMID: 25016930; PMCID: PMC4188277. 14: Kang S, Lee D, Theusch BE, Arpey CJ, Brennan TJ. Wound hypoxia in deep tissue after incision in rats. Wound Repair Regen. 2013 Sep-Oct;21(5):730-9. doi: 10.1111/wrr.12081. Epub 2013 Aug 8. PMID: 23926943; PMCID: PMC3776009. 15: Zhang Y, Chen X, Ren P, Su Z, Cao H, Zhou J, Zou X, Fu S, Lin S, Fan J, Yang B, Sun X, Zhou Y, Chen Y, Yang L, Wu J. Synergistic effect of combination topotecan and chronomodulated radiation therapy on xenografted human nasopharyngeal carcinoma. Int J Radiat Oncol Biol Phys. 2013 Oct 1;87(2):356-62. doi: 10.1016/j.ijrobp.2013.05.047. Epub 2013 Jul 29. PMID: 23906928. 16: Horai N, Nagaoka T, Higuchi I, Kasai H, Yoshioka T, Umekita Y, Fukuzaki K, Nagata R, Miyata A, Abeyama K. Muscle wasting associated with pathologic change is a risk factor for the exacerbation of joint swelling in collagen-induced arthritis in cynomolgus monkeys. BMC Musculoskelet Disord. 2013 Jul 9;14:205. doi: 10.1186/1471-2474-14-205. PMID: 23834772; PMCID: PMC3710207. 17: Lancerotto L, Chin MS, Freniere B, Lujan-Hernandez JR, Li Q, Vasquez AV, Bassetto F, Del Vecchio DA, Lalikos JF, Orgill DP. Mechanisms of action of external volume expansion devices. Plast Reconstr Surg. 2013 Sep;132(3):569-578. doi: 10.1097/PRS.0b013e31829ace30. PMID: 23676966. 18: McCall KC, Humm JL, Bartlett R, Reese M, Carlin S. Copper-64-diacetyl- bis(N(4)-methylthiosemicarbazone) pharmacokinetics in FaDu xenograft tumors and correlation with microscopic markers of hypoxia. Int J Radiat Oncol Biol Phys. 2012 Nov 1;84(3):e393-9. doi: 10.1016/j.ijrobp.2012.05.005. Epub 2012 Jun 23. PMID: 22727887; PMCID: PMC3522091. 19: Del Bigio MR, Khan OH, da Silva Lopes L, Juliet PA. Cerebral white matter oxidation and nitrosylation in young rodents with kaolin-induced hydrocephalus. J Neuropathol Exp Neurol. 2012 Apr;71(4):274-88. doi: 10.1097/NEN.0b013e31824c1b44. PMID: 22437339. 20: Grahl N, Puttikamonkul S, Macdonald JM, Gamcsik MP, Ngo LY, Hohl TM, Cramer RA. In vivo hypoxia and a fungal alcohol dehydrogenase influence the pathogenesis of invasive pulmonary aspergillosis. PLoS Pathog. 2011 Jul;7(7):e1002145. doi: 10.1371/journal.ppat.1002145. Epub 2011 Jul 21. PMID: 21811407; PMCID: PMC3141044.

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