NITROSCANATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H8N2O3S
Molecular Weight	272.279
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][N+](=O)C1=CC=C(OC2=CC=C(C=C2)N=C=S)C=C1

InChI

InChIKey=SVMGVZLUIWGYPH-UHFFFAOYSA-N

InChI=1S/C13H8N2O3S/c16-15(17)11-3-7-13(8-4-11)18-12-5-1-10(2-6-12)14-9-19/h1-8H

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/vet/lopatol-500-can.html
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/444159 and http://parasitipedia.net/index.php?option=com_content&view=article&id=2525&Itemid=2799

Nitroscanate (trade name Lopatol) is a medium-spectrum anthelmintic used on dogs and cats. It is available in the form of tablets for oral administration. It is not used on livestock. Nitroscanate is effective against the major gastrointestinal roundworms (nematodes) of dogs and cats (e.g.Toxocara canis, Toxocara cati, Ancylostoma spp, Uncinaria stenocephala) and tapeworms (e.g. Dipylidium caninum, Echinococcus granulosus, Taenia spp, etc.). The molecular mode of action of nitroscanate has not been elucidated. It is assumed that it acts as an uncoupler of the oxidative phosphorylation in the cell mitochondria, which disturbs the production of ATP, the cellular "fuel". This impairs the parasites motility and probably other processes as well.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
ATP biosynthetic process 6 Target ID: GO:0006754 Sources: http://link.springer.com/referenceworkentry/10.1007/3-540-29835-5_2097	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infestation with parasitic worms 2 Sources: https://www.drugs.com/vet/lopatol-500-can.html	Curative		Approved 8429	Lopatol Approved Use Lopatol is indicated for the treatment of infestations in dogs of: Roundworms caused by Toxocara canis, Toxascaris leonina. Hookworms caused by Ancylostoma caninum, Uncinaria stenocephala. Tapeworms caused by Taenia spp., Dipylidium caninum. Launch Date 1996

PubMed

Title	Date	PubMed
The effect of nitroscanate on Echinococcus granulosus and Taenia hydatigena infections in dogs.	1975 Sep	1172624
The effect of micronised nitroscanate on Echinococcus granulosus and Taenia hydatigena infections in dogs.	1977 May	877440
Nitroscanate A new broad spectrum anthelmintic against nematodes and cestodes of dogs and cats.	1979 Feb	444159
Oral pharmacological treatments for parasitic diseases of rainbow trout Oncorhynchus mykiss. II. Gyrodactylus sp.	1998 Jul 30	9745715
Continuous feed medication with nitroscanate for the removal of Hymenolepis nana in naturally infected mice and rats.	2001 Oct	11721592

Patents

Sample Use Guides

In Vivo Use Guide

For roundworms, hookworms and tapeworms. 50 mg/kg of body weight - one 100 mg tablet per 2 kg body weight or - one 500 mg tablet per 10 kg body weight.

Route of Administration: Oral

In Vitro Use Guide

In vitro, a concentration of 156.25 mg 1(-1) failed to kill all the helminths Gyrodactylus sp. obtained from rainbow trout, but in vivo all concentrations equal to, or greater than, 0.07 mg 1(-1) were 100% effective;

Name

Type

Language

NITROSCANATE

Official Name

English

CGA-23654

Code

English

NITROSCANATE [MART.]

Common Name

English

NITROSCANATE [MI]

Common Name

English

nitroscanate [INN]

Common Name

English

NITROSCANATE [USAN]

Common Name

English

BENZENE, 1-ISOTHIOCYANATO-4-(4-NITROPHENOXY)-

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QP52AX01