Niridazole

Last updated
Niridazole
Niridazole.svg
Clinical data
MedlinePlus a682128
ATC code
Identifiers
  • 1-(5-Nitro-1,3-thiazol-2-yl)imidazolidin-2-one
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.466 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C6H6N4O3S
Molar mass 214.20 g·mol−1
3D model (JSmol)
  • C1CN(C(=O)N1)C2=NC=C(S2)[N+](=O)[O-]
  • 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) X mark.svgN
  • Key:RDXLYGJSWZYTFJ-UHFFFAOYSA-N X mark.svgN
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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 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.[ citation needed ]

References

  1. Tracy JW, Catto BA, Webster LT (September 1983). "Reductive metabolism of niridazole by adult Schistosoma mansoni. Correlation with covalent drug binding to parasite macromolecules". Molecular Pharmacology. 24 (2): 291–9. PMID   6193406.
  2. Toxicology Data Network – Niridazole
  3. Katz N (November 1975). "Clinical evaluation of niridazole and hycanthone in schistosomiasis mansoni endemic areas". Journal of Toxicology and Environmental Health. 1 (2): 203–9. Bibcode:1975JTEHA...1..203K. doi:10.1080/15287397509529322. PMID   1107578.
  4. Barat R, Srinatha A, Pandit JK, Mittal N, Anupurba S (November 2007). "Ethylcellulose inserts of an orphan drug for periodontitis: preparation, in vitro, and clinical studies". Drug Delivery. 14 (8): 531–8. doi:10.1080/10717540701606517. PMID   18027183.
  5. Barat R, Srinatha A, Pandit JK, Ridhurkar D, Balasubramaniam J, Mittal N, Mishra DN (2006). "Niridazole biodegradable inserts for local long-term treatment of periodontitis: possible new life for an orphan drug". Drug Delivery. 13 (5): 365–73. doi:10.1080/10717540500398126. PMID   16877312. S2CID   31987972.