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Key Documents

SML1935

Sigma-Aldrich

Nimorazole

≥98% (HPLC)

Synonym(s):

4-(2-(5-Nitro-1H-imidazol-1-yl)ethyl)morpholine, K 1900, K-1900, K1900, NSC 107524, NSC-107524, NSC107524

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About This Item

Empirical Formula (Hill Notation):
C9H14N4O3
CAS Number:
6506-37-2
Molecular Weight:
226.23
EC Number:
229-394-4
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 30 mg/mL, clear

storage temp.

2-8°C

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

InChI key

MDJFHRLTPRPZLY-UHFFFAOYSA-N

Biochem/physiol Actions

Nimorazole is a nitroimidazole-based hypoxic cell-radiation sensitizer with less toxicity than etanidazole or misonidazole. Under low oxygen (hypoxic) condition, reductive activation of its 5-nitroimidazole moiety leads to enhanced adduct formation with reduced glutathione, which form the basis of cancer/tumour-selective radiation sensitization. Nimorazole is also a known anti-infective agent against trichomoniasis, an infectious disease caused by the protozoan parasite Trichomonas vaginalis.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H340,H361d

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
Mohamed A Hassan Metwally et al.
Acta oncologica (Stockholm, Sweden), 54(9), 1673-1677 (2015-09-24)
Thomas M Ashton et al.
Nature communications, 7, 12308-12308 (2016-07-28)
Tumour hypoxia renders cancer cells resistant to cancer therapy, resulting in markedly worse clinical outcomes. To find clinical candidate compounds that reduce hypoxia in tumours, we conduct a high-throughput screen for oxygen consumption rate (OCR) reduction and identify a number
Thomas R Wittenborn et al.
Acta oncologica (Stockholm, Sweden), 54(9), 1385-1392 (2015-09-04)
Hypoxia is a characteristic feature of solid tumours that significantly reduces the efficacy of conventional radiation therapy. In this study we investigated the role of hypoxia in a stereotactic radiation schedule by using a variety of hypoxic modifiers in a

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