Niridazole

• CAS: 61-57-4
• Catalog Number: ACM61574
• Category: Main Products
• Molecular Weight: 214.2
• Molecular Formula: C6H6N4O3S

Case Study

Niridazole as a Lead Compound for Organometallic Derivatization against Schistosomiasis

Karpstein, Tanja, et al. ChemMedChem 20.23 (2025): e202500603.

Niridazole, a nitrothiazole schistosomicide, serves as the lead scaffold whose derivatization with ferrocenyl, ruthenocenyl and benzyl moieties generates drug candidates with improved potency against Schistosoma mansoni for the treatment of schistosomiasis.
Experimental Protocol: Ten derivatives are prepared either by amide coupling of the niridazole core with activating agents in dimethylformamide at room temperature overnight (64-85% yield) or by N-alkylation with bromide derivatives in acetonitrile under reflux, and all compounds are characterized by NMR, mass spectrometry and elemental analysis. Representative derivatives remain stable in DMSO-d6 solution for 48 h. Drug efficacy is tested in vitro against newly transformed schistosomula, juvenile and adult worms incubated with 50 micromolar compound for 72 h at 37°C and 5% CO₂, with viability scored microscopically.
Performance Evaluation: Niridazole shows an EC₅₀ of 5.6 micromolar against adult schistosomes, whereas the ethenyl-ferrocenyl derivative reaches 1.5 micromolar, a 3.8-fold improvement, and the ruthenocenyl and ferrocenyl analogs reach 3.2 and 3.5 micromolar. One carbonyl-linked derivative displays pan-stage activity with an EC₅₀ of 2.0 micromolar against schistosomula. The adamantyl analog acts rapidly, reaching an EC₅₀ below 10 micromolar within 24 h, whereas niridazole requires 48 h. No cytotoxic effects are observed for the active series in hepatocyte and neuroblastoma cell lines.

Custom Q&A

What is the molecular formula of Niridazole?

The molecular formula of Niridazole is C6H6N4O3S.

What is the molecular weight of Niridazole?

The molecular weight of Niridazole is 214.20 g/mol.

What is the IUPAC name of Niridazole?

The IUPAC name of Niridazole is 1-(5-nitro-1,3-thiazol-2-yl)imidazolidin-2-one.

What is the InChIKey of Niridazole?

The InChIKey of Niridazole is RDXLYGJSWZYTFJ-UHFFFAOYSA-N.

What are the synonyms of Niridazole?

The synonyms of Niridazole include Nitrothiazol, Nitrothiazole, Nitrothiamidazol.

What is the CAS number of Niridazole?

The CAS number of Niridazole is 61-57-4.

What is the melting point of Niridazole?

The melting point of Niridazole is 260-262 °C.

What is the hydrogen bond donor count of Niridazole?

The hydrogen bond donor count of Niridazole is 1.

What is the hydrogen bond acceptor count of Niridazole?

The hydrogen bond acceptor count of Niridazole is 5.

Is Niridazole canonicalized?

Yes, Niridazole is canonicalized.