NIRIDAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H6N4O3S
Molecular Weight	214.202
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CN=C(S1)N2CCNC2=O

InChI

InChIKey=RDXLYGJSWZYTFJ-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Description
Sources: https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/f?./temp/~eSzPpi:3 | Anand, N. & Sharma, S. (1997) Approaches to Design and Synthesis of Antiparasitic Drugs, page 267, retrieved from: https://books.google.ru/books?id=QR9sE9hZzBwC | https://www.ncbi.nlm.nih.gov/pubmed/7044324 | http://apps.who.int/medicinedocs/en/d/Jwhozip48e/10.1.html

Niridazole is used (but not officially recommended) for the treatment of schistosomiasis, dracunculiasis and tungiasis. The mode of action of niridazole is not fully understood. The major action of niridazole seems to be on the glycogen metabolism of the helminths. The drug also case structural damage to the reproductive system of female schistosomes. Another possible mechanism of action of niridazole involves the inhibition of DNA synthesis in schistosomes. It is metabolized in the liver. The most serious side effects were those connected with the nervous area (convulsion, hallucination, etc.).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
glycogen metabolic process 1 Target ID: GO:0005977 Sources: Anand, N. & Sharma, S. (1997) Approaches to Design and Synthesis of Antiparasitic Drugs, page 267, retrieved from: https://books.google.ru/books?id=QR9sE9hZzBwC	Modulator 846
DNA biosynthetic process 6 Target ID: GO:0071897 Sources: Anand, N. & Sharma, S. (1997) Approaches to Design and Synthesis of Antiparasitic Drugs, page 267, retrieved from: https://books.google.ru/books?id=QR9sE9hZzBwC	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Schistosomiasis 32 Sources: Aronson, J.K. (2009) Meyler's Side Effects of Antimicrobial Drugs, retrieved from: https://books.google.ru/books?id=Zu2s5QBqiEkC	Curative	Phase II 1147	Unknown Approved Use Unknown
Dracunculiasis 1 Sources: Aronson, J.K. (2009) Meyler's Side Effects of Antimicrobial Drugs, retrieved from: https://books.google.ru/books?id=Zu2s5QBqiEkC	Curative	Phase II 1147	Unknown Approved Use Unknown
Tungiasis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7044324	Curative	Phase II 1147	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
40 mg/kg 1 times / day multiple, oral Highest studied dose Dose: 40 mg/kg, 1 times / day Route: oral Route: multiple Dose: 40 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/ https://pubmed.ncbi.nlm.nih.gov/5331463/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/ https://pubmed.ncbi.nlm.nih.gov/5331463/	Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/ https://pubmed.ncbi.nlm.nih.gov/5331463/
34 mg/kg 1 times / day multiple, oral Studied dose Dose: 34 mg/kg, 1 times / day Route: oral Route: multiple Dose: 34 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/	Other AEs: Death... Other AEs: Death Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/

AEs

AE	Significance	Dose	Population
Death		34 mg/kg 1 times / day multiple, oral Studied dose Dose: 34 mg/kg, 1 times / day Route: oral Route: multiple Dose: 34 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5917843/

PubMed

Title	Date	PubMed
Transcriptomes and pathways associated with infectivity, survival and immunogenicity in Brugia malayi L3.	2009-06-15	19527522
Genotoxicity revaluation of three commercial nitroheterocyclic drugs: nifurtimox, benznidazole, and metronidazole.	2009	20981287
Ethylcellulose inserts of an orphan drug for periodontitis: preparation, in vitro, and clinical studies.	2007-11	18027183
Niridazole biodegradable inserts for local long-term treatment of periodontitis: possible new life for an orphan drug.	2006-08-01	16877312
Safety of the methylene blue plus chloroquine combination in the treatment of uncomplicated falciparum malaria in young children of Burkina Faso [ISRCTN27290841].	2005-09-22	16179085
Anthelmintics: a review.	2002-04-20	11963321
An in vivo evaluation of induction of abnormal sperm morphology by some anthelmintic drugs in mice.	2001-10-18	11525915
Oxamniquine versus niridazole for treatment of uncomplicated Schistosoma mansoni infection.	1982-11	7149102
Treatment of amebic liver abscess with emetine hydrochloride, niridazole, and metronidazole. A controlled clinical trial.	1974-07	4603136

Patents

Sample Use Guides

In Vivo Use Guide

25 mg/kg given for 5-7 days or 30 mg/kg for 4 days

Route of Administration: Oral

In Vitro Use Guide

Niridazole was dissolved in dimethyl sulfoxide to obtain a solution at 1,000 ug/ml. It was further diluted in distilled water and mixed with Mueller-Hinton agar to obtain graded concentrations from 0.001 to 8 ug/ml. The minimal inhibitory concentrations of niridazole for C. fetus subsp. Jejeuni was substantially higher than that of metronidazole. The break point of niridazole may tentatively be fixed between 4 and 8 ug/ml of active drug.

Name

Type

Language

BA 32644

Preferred Name

English

NIRIDAZOLE

Official Name

English

NSC-136947

Code

English

CIBA 32644BA

Code

English

BA-32644

Code

English

NIRIDAZOLE [USAN]

Common Name

English

NIRIDAZOLE [MART.]

Common Name

English

NIRIDAZOLE [IARC]

Common Name

English

Niridazole [WHO-DD]

Common Name

English

niridazole [INN]

Common Name

English

NIRIDAZOLUM [WHO-IP LATIN]

Common Name

English

NIRIDAZOLE [HSDB]

Common Name

English

NIRIDAZOLE [WHO-IP]

Common Name

English

NIRIDAZOLE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C277