Niridazole

Niridazole

Systematic (IUPAC) name
1-(5-nitro-1,3-thiazol-2-yl)imidazolidin-2-one
Clinical data
MedlinePlus	a682128
Identifiers
CAS Number	61-57-4
ATC code	P02BX02 (WHO)
PubChem	CID 6093
ChemSpider	5868
UNII	N116U8Y5QQ
KEGG	D05170
Chemical data
Formula	C6H6N4O3S
Molar mass	214.20 g/mol
SMILES C1CN(C(=O)N1)C2=NC=C(S2)[N+](=O)[O-]
InChI InChI=1S/C6H6N4O3S/c11-5-7-1-2-9(5)6-8-3-4(14-6)10(12)13/h3H,1-2H2,(H,7,11) Key:RDXLYGJSWZYTFJ-UHFFFAOYSA-N
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Niridazole is a schistosomicide.^[1] It is used to treat schistosomiasis, the helmintic disease caused by certain flatworms (trematodes) from the genus Schistosoma (formerly Bilharzia). It is also known by its trade name Ambilhar. It is usually is given as tablets.

Niridazole has central nervous system toxicity and can cause dangerous side effects, such as hallucinations.^[2] Also, it may cause allergic reactions in sensitive people. However, it is one of the most effective schistosomicide drugs.^[3]

It has recently also been investigated for use in the treatment of periodontitis.^[4][5]

Mechanism of action

Niridazole is rapidly concentrated in the parasite and inhibits oogenesis and spermatogenesis. The compound also inhibits the phosphofructokinase enzyme, leading to glycogen depletion and hepatic shift.

References

1. Tracy, J. W.; Catto, B. A.; Webster Lt, L. T. (1983). "Reductive metabolism of niridazole by adult Schistosoma mansoni. Correlation with covalent drug binding to parasite macromolecules". Molecular Pharmacology 24 (2): 291–299. PMID 6193406.
2. Toxicology Data Network – Niridazole
3. Katz, N (1975). "Clinical evaluation of niridazole and hycanthone in schistosomiasis mansoni endemic areas". Journal of Toxicology and Environmental Health 1 (2): 203–9. doi:10.1080/15287397509529322. PMID 1107578.
4. Barat, R.; Srinatha, A.; Pandit, J.; Mittal, N.; Anupurba, S. (2007). "Ethylcellulose inserts of an orphan drug for periodontitis: preparation, in vitro, and clinical studies". Drug delivery 14 (8): 531–538. doi:10.1080/10717540701606517. PMID 18027183.
5. Barat, R.; Srinatha, A.; Pandit, J.; Ridhurkar, D.; Balasubramaniam, J.; Mittal, N.; Mishra, D. (2006). "Niridazole biodegradable inserts for local long-term treatment of periodontitis: possible new life for an orphan drug". Drug delivery 13 (5): 365–373. doi:10.1080/10717540500398126. PMID 16877312.