CAS 7681-76-7 Ronidazole - Analytical Products / Alfa Chemistry

CAT	APS7681767
CAS	7681-76-7
Structure
Synonyms	Ronidazole, (1-Methyl-5-nitro-imidazol-2-yl)methyl carbamate
IUPAC Name	(1-methyl-5-nitroimidazol-2-yl)methyl carbamate
Molecular Weight	200.15
Molecular Formula	C6H8N4O4
Canonical SMILES	Cn1c(COC(=O)N)ncc1[N+](=O)[O-]
InChI	InChI=1S/C6H8N4O4/c1-9-4(3-14-6(7)11)8-2-5(9)10(12)13/h2H,3H2,1H3,(H2,7,11)

Accurate Mass	200.0546
Format	Neat
Shipping	Room Temperature
Storage Conditions	-18°C
Subcategory	Pharmaceutical and veterinary compounds and metabolites, EU Methods

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Case Study

Ronidazole Used for the Controlled Induction of Cell Death in Drosophila via Nitroreductase-Mediated Activation

Teeters, Gary, et al. Developmental Biology 520 (2025): 31-40.

Ronidazole, a nitroimidazole prodrug, has been successfully repurposed as a molecular tool for genetically controlled cell ablation in Drosophila melanogaster. In this system, Ronidazole is bioactivated by the bacterial enzyme nitroreductase (NTR), which converts the prodrug into cytotoxic intermediates, leading to targeted DNA damage and caspase-dependent apoptosis. This innovative approach integrates the GAL4/UAS system for spatially restricted NTR expression with Ronidazole feeding for temporal control, eliminating reliance on temperature shifts or complex genetic manipulations.
At an optimized concentration of 3 mM, Ronidazole induces significant and reproducible wing ablation phenotypes in adult flies expressing NTR, including notched, miniaturized, or completely absent wings. Notably, control groups lacking either GAL4 or UAS-NTR did not exhibit such defects, confirming the specificity and efficacy of the Ronidazole-NTR pair. Moreover, the severity of the phenotype correlates with both NTR expression levels and Ronidazole dosage, offering a tunable system for tissue-specific cell death
This methodology represents a powerful alternative to classical genetic ablation techniques. Its temperature-independent, feeding-based activation mechanism avoids the developmental disruptions often associated with heat-inducible systems. Furthermore, the GFP-NTR fusion allows for simultaneous visualization and ablation, enabling high-throughput screening applications in functional genomics.
Ronidazole thus serves as a reliable, versatile reagent for inducible, tissue-specific cell death studies in Drosophila, advancing the toolkit for developmental biology and gene function analysis.

Ronidazole Used for the Preparation of Transition Metal Coordination Complexes with Diverse Chelation Modes and Supramolecular Architectures

García-Holley, Paula, et al. Polyhedron 104 (2016): 127-137.

Ronidazole, a nitroimidazole derivative, has demonstrated remarkable versatility as a ligand in the synthesis of coordination complexes with various transition metals including Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II). Its coordination behavior is governed by both the nature of the metal ion and the type of counterion, allowing for the formation of structurally diverse chelate rings and complex geometries.
In halide-based complexes of Co(II), Cu(II), Zn(II), Cd(II), and Hg(II), ronidazole acts as a bidentate ligand through its imidazolic nitrogen and the oxygen of the carbamate C-O-C group, forming stable five-membered chelate rings. Conversely, in nitrate-based complexes of Co(II), Ni(II), and Cu(II), and halide complexes of Ni(II), the ligand coordinates via the imidazolic nitrogen and carbonylic C=O oxygen, generating seven-membered chelate rings. These coordination preferences give rise to geometries ranging from tetrahedral and trigonal bipyramidal to octahedral.
X-ray crystallographic analysis revealed that the resulting complexes organize into intricate three-dimensional supramolecular networks. These structures are stabilized by intermolecular forces such as hydrogen bonding, lone pair···π interactions (NO···π), and halogen···π (X···π) contacts.
These findings highlight Ronidazole's potential as a tunable ligand for the rational design of metal-organic frameworks (MOFs), supramolecular assemblies, and coordination polymers with potential applications in catalysis, sensing, and molecular materials.