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 828
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 8297

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 1132	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 1132	Unknown Approved Use Unknown
Tungiasis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7044324	Curative	Phase II 1132	Unknown Approved Use Unknown

PubMed

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

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

NIRIDAZOLE

Official Name

English

BA 32644

Code

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