Nimorazole HCl | CAS# 94107-55-8 (HCl) | antimicrobial

MedKoo Cat#: 414396 | Name: Nimorazole HCl

Description:

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

Nimorazole HCl is an antimicrobial with activity against anaerobic bacteria and protozoa. Its actions and properties are similar to metronidazole. It has also been used in trials studying the treatment of Hypoxia, Radiotherapy, Hypoxic Modification, Gene Profile, Gene Signature, and Head and Neck Squamous Cell Carcinoma, among others. Azanta is developing, nimorazole, as an oral hypoxic radio-sensitiser for the treatment of patients with head and neck cancer who are undergoing radiotherapy. Previously, nimorazole has been approved for use as an anti-protozoal agent and has been launched worldwide. Nimorazole, for the treatment of head and neck cancer patients undergoing radiotherapy received orphan designation by EMA in 2011.

Chemical Structure

Nimorazole HCl

CAS# 94107-55-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 414396

Name: Nimorazole HCl

CAS#: 94107-55-8 (HCl)

Chemical Formula: C9H15ClN4O3

Exact Mass: 0.0000

Molecular Weight: 262.69

Elemental Analysis: C, 41.15; H, 5.76; Cl, 13.49; N, 21.33; O, 18.27

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

94107-55-8 (HCl) 6506-37-2 (free base)

Synonym

Nimorazole hydrochloride; Nimorazole HCl

IUPAC/Chemical Name

4-(2-(5-Nitro-1H-imidazole-1-yl)ethyl)morpholine monohydrochloride

InChi Key

YNZSADJOMNVVST-UHFFFAOYSA-N

InChi Code

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

SMILES Code

O=[N+](C1=CN=CN1CCN2CCOCC2)[O-].[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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 262.69 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.

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

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.