Niridazole

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MedKoo CAT#: 584122

CAS#: 61-57-4

Description: Niridazole can be used to treat schistosomiasis, the helmintic disease caused by certain flatworms (trematodes) from the genus Schistosoma (formerly Bilharzia), although it has central nervous system toxicity. 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. It has also been studied as biodegradable inserts for local long-term treatment of periodontitis.


Price and Availability

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Pricing updated 2020-11-23. Prices are subject to change without notice.

Niridazole is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 584122
Name: Niridazole
CAS#: 61-57-4
Chemical Formula: C6H6N4O3S
Exact Mass: 214.0161
Molecular Weight: 214.19
Elemental Analysis: C, 33.64; H, 2.82; N, 26.16; O, 22.41; S, 14.97


Synonym: Niridazole; Ambilhar; BA 32644; BA-32644; BA32644

IUPAC/Chemical Name: 2-Imidazolidinone, 1-(5-nitro-2-thiazolyl)-

InChi Key: RDXLYGJSWZYTFJ-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C1NCCN1C2=NC=C([N+]([O-])=O)S2


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Barat R, Srinatha A, Pandit JK, Ridhurkar D, Balasubramaniam J, Mittal N, Mishra DN. Niridazole biodegradable inserts for local long-term treatment of periodontitis: possible new life for an orphan drug. Drug Deliv. 2006 Sep-Oct;13(5):365-73. PubMed PMID: 16877312.

2: Fantel AG, Juchau MR, Tracy JW, Burroughs CJ, Person RE. Studies of mechanisms of niridazole-elicited embryotoxicity: evidence against a major role for covalent binding. Teratology. 1989 Jan;39(1):63-74. PubMed PMID: 2718141.

3: Wade WG, Addy M. Comparison of in vitro activity of niridazole, metronidazole and tetracycline against subgingival bacteria in chronic periodontitis. J Appl Bacteriol. 1987 Nov;63(5):455-7. PubMed PMID: 3440767.

4: Ma Z, Si BX, Liu YL, Huang LS. [Synthesis of acylates of niridazole and its analogs as schistosomicides]. Yao Xue Xue Bao. 1989;24(6):476-80. Chinese. PubMed PMID: 2609988.

5: Yarlett N, Hof H, Yarlett NC. Activities of metronidazole and niridazole against Trichomonas vaginalis clinical isolates. J Antimicrob Chemother. 1987 Jun;19(6):767-70. PubMed PMID: 3497149.

6: Bannatyne RM, Jackowski J. Antimicrobial effects of niridazole on Gardnerella vaginalis. Infection. 1987 Mar-Apr;15(2):128. PubMed PMID: 3496279.

7: Mohtashamipur E, Norpoth K. Excretion of mutagens in sweat and faeces of man, and in serum, gastric juice and urine of rats, after oral dosing of niridazole or metronidazole. Mutagenesis. 1986 Sep;1(5):371-4. PubMed PMID: 3331676.

8: Abdu-Aguye I, Sambo-Donga L. Influence of dosing interval and in-patient versus out-patient status on incidence of side-effects of niridazole. Hum Toxicol. 1986 Jul;5(4):275-8. PubMed PMID: 3089911.

9: Bannatyne RM, Jackowski J, Grant RB. Antibacterial activity of niridazole against Salmonellae. Antimicrob Agents Chemother. 1986 May;29(5):923-4. PubMed PMID: 3729350; PubMed Central PMCID: PMC284181.

10: West BC. Niridazole-induced red/brown urine pigment is associated with increased urinary beta-glucuronidase excretion and a bladder site of formation. Res Commun Chem Pathol Pharmacol. 1986 Apr;52(1):107-17. PubMed PMID: 3086953.

11: Fantel AG, Greenaway JC, Walker E, Juchau MR. The toxicity of niridazole in rat embryos in vitro. Teratology. 1986 Feb;33(1):105-12. PubMed PMID: 3738802.

12: el-Zayadi A, el Fakhfakh A, Fawzy Montasser M, Soltan YA. Effect of the oral antibilharzial niridazole (ambilhar) on patients with concomitant schistosomiasis and HBs antigenaemia. Hepatogastroenterology. 1985 Aug;32(4):168-70. PubMed PMID: 4054810.

13: Oduah IN, Thabrew MI, Emerole GO. Covalent binding and glutathione depletion in the rat following niridazole (ambilhar) pretreatment. Arch Toxicol. 1985 Apr;57(1):17-24. PubMed PMID: 4015394.

14: Orlowski T, Smogorzewski M, Kurkus J. Niridazole as an adjunct to "conventional" immunosuppression in kidney allograft transplantation. Long-term follow up. Arch Immunol Ther Exp (Warsz). 1985;33(6):797-801. PubMed PMID: 3914251.

15: Speck WT, Carr HS, Rosenkranz HS. Niridazole: Evidence for promutagenic events involving guanine-cytosine and adenine-thymine base pairs. Environ Mutagen. 1985;7(4):429-37. PubMed PMID: 3902461.

16: Sainis KB, Gadgil MB, Phondke GP. Niridazole-mediated modulation of suppressor cells in Wistar rats. Immunopharmacology. 1984 Oct;8(2):61-8. PubMed PMID: 6239839.

17: Valencia CI, Catto BA, Fairchild EH, Wilson SB, Maramba NC, Webster LT Jr. Concentration-time course of niridazole and six metabolites in the serum of four Filipinos with Schistosoma japonicum infection. J Pharmacol Exp Ther. 1984 Jul;230(1):133-40. PubMed PMID: 6547741.

18: Oduah IN, Thabrew MI, Emerole GO. Covalent binding of niridazole (Ambilhar) to tissue proteins of the rat. Chem Biol Interact. 1984 May;49(3):299-310. PubMed PMID: 6722942.

19: Rey JL, Sellin E, Sellin B, Simonkovich E, Mouchet F. [Comparative efficacy of oltipraz (1 dose, 30 mg/kg) and the combination of niridazole (25 mg/kg) and metrifonate (10 mg/kg) against S. haematobium]. Med Trop (Mars). 1984 Apr-Jun;44(2):155-8. French. PubMed PMID: 6482729.

20: Zimber A, Heller ED, Perk K, Ianconescu M, Yaniv A. Effect of lymphoproliferative disease virus and of niridazole on the in vitro blastogenic response of peripheral blood lymphocytes of turkeys. Avian Dis. 1983 Oct-Dec;27(4):1012-24. PubMed PMID: 6197055.