Nimorazole
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MedKoo CAT#: 206778

CAS#: 6506-37-2 (free base)

Description: Nimorazole is a hypoxic radiosensitizer potentially useful in the treatment of patients with head and neck squamous cell carcinoma (HNSCC).

Chemical Structure

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Nimorazole
CAS# 6506-37-2 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 206778
Name: Nimorazole
CAS#: 6506-37-2 (free base)
Chemical Formula: C9H14N4O3
Exact Mass: 226.11
Molecular Weight: 226.236
Elemental Analysis: C, 47.78; H, 6.24; N, 24.77; O, 21.22

Price and Availability

Size Price Availability Quantity
25mg USD 150 2 Weeks
50mg USD 250 2 Weeks
100mg USD 450 2 Weeks
200mg USD 750 2 Weeks
500mg USD 1650 2 Weeks
1g USD 2450 2 Weeks
2g USD 4350 2 Weeks
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Related CAS #: 94107-55-8 (HCl)   6506-37-2 (free base)  

Synonym: Nimorazole

IUPAC/Chemical Name: 4-[2-(5-nitroimidazol-1-yl)ethyl]morpholine

InChi Key: MDJFHRLTPRPZLY-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H14N4O3/c14-13(15)9-7-10-8-12(9)2-1-11-3-5-16-6-4-11/h7-8H,1-6H2

SMILES Code: O=[N+](C1=CN=CN1CCN2CCOCC2)[O-]

Appearance: Light yellow 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
Instruction:
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Biological target: Nimorazole (K-1900), a 2-nitroimidazole, is a hypoxic cell-radiation sensitizer.
In vitro activity: This study shows that LEEs effectively cause the reduction of the radiosensitiser nimorazole via associative electron attachment with the cross-section exceeding most of known molecules. This supports the hypothesis that nimorazole is selectively cytotoxic to tumour cells due to reduction of the molecule as prerequisite for accumulation in the cell. Reference: Nat Commun. 2019 Jun 3;10(1):2388. https://pubmed.ncbi.nlm.nih.gov/31160602/
In vivo activity: This study investigated the radiosensitizing effect of the hypoxia modifier nimorazole in vitro and in vivo. In vitro, pre-treatment with nimorazole significantly decreased hypoxic radioresistance (P < 0.01) while in vivo, nimorazole enhanced the efficacy of RT to suppress cancer cell proliferation in hypoxic tumor areas (Ki67, P = 0.064), but did not affect macroscopic tumor growth. Reference: Radiat Oncol. 2018 Mar 7;13(1):39. https://pubmed.ncbi.nlm.nih.gov/29514673/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 10.0 44.20
DMF:PBS (pH 7.2) (1:3) 0.3 1.11
DMSO 29.4 130.14
Ethanol 2.0 8.84

Preparing Stock Solutions

The following data is based on the product molecular weight 226.24 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. Meißner R, Kočišek J, Feketeová L, Fedor J, Fárník M, Limão-Vieira P, Illenberger E, Denifl S. Low-energy electrons transform the nimorazole molecule into a radiosensitiser. Nat Commun. 2019 Jun 3;10(1):2388. doi: 10.1038/s41467-019-10340-8. PMID: 31160602; PMCID: PMC6546713. 2. Minn H, Clavo AC, Fisher SJ, Wahl RL. Effect of nitroimidazole sensitizers on in vitro glycolytic metabolism of hypoxic squamous cell carcinoma. Acta Oncol. 2000;39(2):199-205. doi: 10.1080/028418600430770. PMID: 10859011. 3. Melsens E, De Vlieghere E, Descamps B, Vanhove C, Kersemans K, De Vos F, Goethals I, Brans B, De Wever O, Ceelen W, Pattyn P. Hypoxia imaging with 18F-FAZA PET/CT predicts radiotherapy response in esophageal adenocarcinoma xenografts. Radiat Oncol. 2018 Mar 7;13(1):39. doi: 10.1186/s13014-018-0984-3. PMID: 29514673; PMCID: PMC5842657.
In vitro protocol: 1. Meißner R, Kočišek J, Feketeová L, Fedor J, Fárník M, Limão-Vieira P, Illenberger E, Denifl S. Low-energy electrons transform the nimorazole molecule into a radiosensitiser. Nat Commun. 2019 Jun 3;10(1):2388. doi: 10.1038/s41467-019-10340-8. PMID: 31160602; PMCID: PMC6546713. 2. Minn H, Clavo AC, Fisher SJ, Wahl RL. Effect of nitroimidazole sensitizers on in vitro glycolytic metabolism of hypoxic squamous cell carcinoma. Acta Oncol. 2000;39(2):199-205. doi: 10.1080/028418600430770. PMID: 10859011.
In vivo protocol: 1. Melsens E, De Vlieghere E, Descamps B, Vanhove C, Kersemans K, De Vos F, Goethals I, Brans B, De Wever O, Ceelen W, Pattyn P. Hypoxia imaging with 18F-FAZA PET/CT predicts radiotherapy response in esophageal adenocarcinoma xenografts. Radiat Oncol. 2018 Mar 7;13(1):39. doi: 10.1186/s13014-018-0984-3. PMID: 29514673; PMCID: PMC5842657.

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1: Hassan Metwally MA, Jansen JA, Overgaard J. Study of the population pharmacokinetic characteristics of nimorazole in head and neck cancer patients treated in the DAHANCA-5 trial. Clin Oncol (R Coll Radiol). 2015 Mar;27(3):168-75. doi: 10.1016/j.clon.2014.11.024. PubMed PMID: 25530485.

2: Tran LB, Bol A, Labar D, Cao-Pham TT, Jordan B, Grégoire V, Gallez B. Predictive value of (18)F-FAZA PET imaging for guiding the association of radiotherapy with nimorazole: a preclinical study. Radiother Oncol. 2015 Feb;114(2):189-94. doi: 10.1016/j.radonc.2014.12.015. PubMed PMID: 25616539.

3: Metwally MA, Frederiksen KD, Overgaard J. Compliance and toxicity of the hypoxic radiosensitizer nimorazole in the treatment of patients with head and neck squamous cell carcinoma (HNSCC). Acta Oncol. 2014 May;53(5):654-61. doi: 10.3109/0284186X.2013.864050. PubMed PMID: 24328536.

4: Das S, Dubey R, Roychowdhury S, Ghosh M, Sinha BN, Kumar Pradhan K, Bal T, Muthukrishnan V, Seijas JA, Pujarid A. A rapid and sensitive determination of hypoxic radiosensitizer agent nimorazole in rat plasma by LC-MS/MS and its application to a pharmacokinetic study. Biomed Chromatogr. 2015 Oct;29(10):1575-80. doi: 10.1002/bmc.3461. PubMed PMID: 25845449.

5: Bentzen J, Toustrup K, Eriksen JG, Primdahl H, Andersen LJ, Overgaard J. Locally advanced head and neck cancer treated with accelerated radiotherapy, the hypoxic modifier nimorazole and weekly cisplatin. Results from the DAHANCA 18 phase II study. Acta Oncol. 2015 Jul;54(7):1001-7. doi: 10.3109/0284186X.2014.992547. PubMed PMID: 25629651.

6: Hassan Metwally MA, Ali R, Kuddu M, Shouman T, Strojan P, Iqbal K, Prasad R, Grau C, Overgaard J. IAEA-HypoX. A randomized multicenter study of the hypoxic radiosensitizer nimorazole concomitant with accelerated radiotherapy in head and neck squamous cell carcinoma. Radiother Oncol. 2015 Jul;116(1):15-20. doi: 10.1016/j.radonc.2015.04.005. PubMed PMID: 25913070.

7: Feketeová L, Plekan O, Goonewardane M, Ahmed M, Albright AL, White J, O'Hair RA, Horsman MR, Wang F, Prince KC. Photoelectron Spectra and Electronic Structures of the Radiosensitizer Nimorazole and Related Compounds. J Phys Chem A. 2015 Oct 1;119(39):9986-95. doi: 10.1021/acs.jpca.5b05950. PubMed PMID: 26344652.

8: Toustrup K, Sørensen BS, Lassen P, Wiuf C, Alsner J, Overgaard J; Danish Head and Neck Cancer Group (DAHANCA).. Gene expression classifier predicts for hypoxic modification of radiotherapy with nimorazole in squamous cell carcinomas of the head and neck. Radiother Oncol. 2012 Jan;102(1):122-9. doi: 10.1016/j.radonc.2011.09.010. PubMed PMID: 21996521.

9: Hassan Metwally MA, Ali R, Kuddu M, Shouman T, Strojan P, Overgaard J, Grau C. Radiotherapy quality assurance of the IAEA-HypoX trial of the accelerated radiotherapy in the treatment of head and neck squamous cell carcinoma with or without the hypoxic radiosensitizer nimorazole. Acta Oncol. 2015;54(9):1673-7. doi: 10.3109/0284186X.2015.1074721. PubMed PMID: 26397148.

10: Thomson D, Yang H, Baines H, Miles E, Bolton S, West C, Slevin N. NIMRAD - a phase III trial to investigate the use of nimorazole hypoxia modification with intensity-modulated radiotherapy in head and neck cancer. Clin Oncol (R Coll Radiol). 2014 Jun;26(6):344-7. doi: 10.1016/j.clon.2014.03.003. PubMed PMID: 24685344.

11: Sugie C, Shibamoto Y, Ito M, Ogino H, Suzuki H, Uto Y, Nagasawa H, Hori H. Reevaluation of the radiosensitizing effects of sanazole and nimorazole in vitro and in vivo. J Radiat Res. 2005 Dec;46(4):453-9. PubMed PMID: 16394636.

12: Bjarnason NH, Christiansen M, Specht L. The nimorazole regimen in patients with head and neck cancer can increase the effect of vitamin K antagonists. Acta Oncol. 2008;47(1):150-1. PubMed PMID: 17851836.

13: Overgaard J, Eriksen JG, Nordsmark M, Alsner J, Horsman MR; Danish Head and Neck Cancer Study Group.. Plasma osteopontin, hypoxia, and response to the hypoxia sensitiser nimorazole in radiotherapy of head and neck cancer: results from the DAHANCA 5 randomised double-blind placebo-controlled trial. Lancet Oncol. 2005 Oct;6(10):757-64. PubMed PMID: 16198981.

14: Henk JM, Bishop K, Shepherd SF. Treatment of head and neck cancer with CHART and nimorazole: phase II study. Radiother Oncol. 2003 Jan;66(1):65-70. PubMed PMID: 12559522.

15: Sørensen BS, Busk M, Olthof N, Speel EJ, Horsman MR, Alsner J, Overgaard J. Radiosensitivity and effect of hypoxia in HPV positive head and neck cancer cells. Radiother Oncol. 2013 Sep;108(3):500-5. doi: 10.1016/j.radonc.2013.06.011. PubMed PMID: 23953409.

16: Bjarnason NH, Specht L, Dalhoff K. Nimorazole may increase the effect of phenprocoumon. Radiother Oncol. 2005 Mar;74(3):345. PubMed PMID: 15763317.

17: Cottrill CP, Bishop K, Walton MI, Henk JM. Pilot study of nimorazole as a hypoxic-cell sensitizer with the "chart" regimen in head and neck cancer. Int J Radiat Oncol Biol Phys. 1998 Nov 1;42(4):807-10. PubMed PMID: 9845101.

18: Lassen P, Eriksen JG, Hamilton-Dutoit S, Tramm T, Alsner J, Overgaard J; Danish Head and Neck Cancer Group (DAHANCA).. HPV-associated p16-expression and response to hypoxic modification of radiotherapy in head and neck cancer. Radiother Oncol. 2010 Jan;94(1):30-5. doi: 10.1016/j.radonc.2009.10.008. PubMed PMID: 19910068.

19: Overgaard J, Hansen HS, Overgaard M, Bastholt L, Berthelsen A, Specht L, Lindeløv B, Jørgensen K. A randomized double-blind phase III study of nimorazole as a hypoxic radiosensitizer of primary radiotherapy in supraglottic larynx and pharynx carcinoma. Results of the Danish Head and Neck Cancer Study (DAHANCA) Protocol 5-85. Radiother Oncol. 1998 Feb;46(2):135-46. PubMed PMID: 9510041.

20: Wittenborn TR, Horsman MR. Targeting tumour hypoxia to improve outcome of stereotactic radiotherapy. Acta Oncol. 2015;54(9):1385-92. doi: 10.3109/0284186X.2015.1064162. PubMed PMID: 26329662.