niridazole

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444347219

| IUPAC_name = 1-(5-Nitro-1,3-thiazol-2-yl)imidazolidin-2-one

| image = Niridazole.svg

| tradename =

| MedlinePlus = a682128

| pregnancy_AU =

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| legal_US =

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| routes_of_administration =

| bioavailability =

| protein_bound =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 61-57-4

| ATC_prefix = P02

| ATC_suffix = BX02

| PubChem = 6093

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = N116U8Y5QQ

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D05170

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 5868

| chemical_formula =

| C=6 | H=6 | N=4 | O=3 | S=1

| smiles = C1CN(C(=O)N1)C2=NC=C(S2)[N+](=O)[O-]

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C6H6N4O3S/c11-5-7-1-2-9(5)6-8-3-4(14-6)10(12)13/h3H,1-2H2,(H,7,11)

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = RDXLYGJSWZYTFJ-UHFFFAOYSA-N

}}

Niridazole is a schistosomicide.{{cite journal | vauthors = Tracy JW, Catto BA, Webster LT | title = Reductive metabolism of niridazole by adult Schistosoma mansoni. Correlation with covalent drug binding to parasite macromolecules | journal = Molecular Pharmacology | volume = 24 | issue = 2 | pages = 291–9 | date = September 1983 | pmid = 6193406 }} 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.[http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/f?./temp/~pr3DeG:1 Toxicology Data Network – Niridazole] Also, it may cause allergic reactions in sensitive people. However, it is one of the most effective schistosomicide drugs.{{cite journal | vauthors = Katz N | title = Clinical evaluation of niridazole and hycanthone in schistosomiasis mansoni endemic areas | journal = Journal of Toxicology and Environmental Health | volume = 1 | issue = 2 | pages = 203–9 | date = November 1975 | pmid = 1107578 | doi = 10.1080/15287397509529322 | bibcode = 1975JTEHA...1..203K }}

It has recently also been investigated for use in the treatment of periodontitis.{{cite journal | vauthors = Barat R, Srinatha A, Pandit JK, Mittal N, Anupurba S | title = Ethylcellulose inserts of an orphan drug for periodontitis: preparation, in vitro, and clinical studies | journal = Drug Delivery | volume = 14 | issue = 8 | pages = 531–8 | date = November 2007 | pmid = 18027183 | doi = 10.1080/10717540701606517 | doi-access = }}{{cite journal | vauthors = Barat R, Srinatha A, Pandit JK, Ridhurkar D, Balasubramaniam J, Mittal N, Mishra DN | title = Niridazole biodegradable inserts for local long-term treatment of periodontitis: possible new life for an orphan drug | journal = Drug Delivery | volume = 13 | issue = 5 | pages = 365–73 | year = 2006 | pmid = 16877312 | doi = 10.1080/10717540500398126 | s2cid = 31987972 }}

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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.{{cn|date=December 2022}}

References