Nimorazole,a nitroimidazole anti-infective, is a hypoxic radiosensitizer potentially useful in the treatment of patients with head and neck squamous cell carcinoma (HNSCC). Nimorazole significantly improves the effect of radiotherapeutic management of supraglottic and pharynx tumors and can be given without major side-effects. Nimorazole is the only such chemical reagent that has shown a significant effect in a randomized controlled trial in head and neck cancer.

Physicochemical Properties

Molecular Formula	C9H14N4O3
Molecular Weight	226.23
Exact Mass	226.106
Elemental Analysis	C, 47.78; H, 6.24; N, 24.77; O, 21.22
CAS #	6506-37-2
Related CAS #	94107-55-8 (HCl);6506-37-2;
PubChem CID	23009
Appearance	Light yellow solid powder
Density	1.4±0.1 g/cm3
Boiling Point	443.0±35.0 °C at 760 mmHg
Flash Point	221.7±25.9 °C
Vapour Pressure	0.0±1.1 mmHg at 25°C
Index of Refraction	1.637
LogP	-0.08
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	16
Complexity	239
Defined Atom Stereocenter Count	0
SMILES	O1C([H])([H])C([H])([H])N(C([H])([H])C1([H])[H])C([H])([H])C([H])([H])N1C([H])=NC([H])=C1[N+](=O)[O-]
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
Chemical Name	4-[2-(5-nitroimidazol-1-yl)ethyl]morpholine
Synonyms	Nimorazole; K-1900; K 1900; K1900
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	In vitro activity: Nimorazole,a nitroimidazole anti-infective, is a hypoxic radiosensitizer potentially useful in the treatment of patients with head and neck squamous cell carcinoma (HNSCC). Nimorazole significantly improves the effect of radiotherapeutic management of supraglottic and pharynx tumors and can be given without major side-effects. Nimorazole is the only such chemical reagent that has shown a significant effect in a randomized controlled trial in head and neck cancer.
ln Vivo
Animal Protocol
References	Radiother Oncol.2003 Jan;66(1):65-70.
Additional Infomation	Nimorazole is a member of imidazoles and a C-nitro compound. Nimorazole has 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. Nimorazole is a water soluble, 5-nitroimidazole compound with antibacterial and potential radiosensitizing activity. As an oxygen mimetic, nimorazole induces free radical formation and is able to sensitize hypoxic cells to the cytotoxic effects of ionizing radiation. This prevents DNA repair and thus enhances damage to DNA strands; eventually, leading to tumor cell death. Nimorazole is less active but also less toxic than the 2-nitroimidazole compounds, misonidazole and etanidazole. An antitrichomonal agent which is effective either topically or orally and whose urinary metabolites are also trichomonicidal.

Solubility Data

Solubility (In Vitro)

DMSO : 33.33 ~45 mg/mL ( 147.33 ~198.91 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.08 mg/mL (9.19 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (9.19 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (9.19 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.08 mg/mL (9.19 mM)  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.4203 mL	22.1014 mL	44.2028 mL
	5 mM	0.8841 mL	4.4203 mL	8.8406 mL
	10 mM	0.4420 mL	2.2101 mL	4.4203 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.