OXYCLOZANIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H6Cl5NO3
Molecular Weight	401.457
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC1=C(NC(=O)C2=C(O)C(Cl)=CC(Cl)=C2Cl)C=C(Cl)C=C1Cl

InChI

InChIKey=JYWIYHUXVMAGLG-UHFFFAOYSA-N

InChI=1S/C13H6Cl5NO3/c14-4-1-6(16)11(20)8(2-4)19-13(22)9-10(18)5(15)3-7(17)12(9)21/h1-3,20-21H,(H,19,22)

HIDE SMILES / InChI

Molecular Formula	C13H6Cl5NO3
Molecular Weight	401.457
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://goo.gl/hjMyxx
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25897961 | https://www.ncbi.nlm.nih.gov/pubmed/25771931

Oxyclozanide is a salicylanilide anthelmintic, used for the treatment and control of fascioliasis in cattle, sheep, and goats. The mechanism of action of oxyclozanide is the uncoupling of oxidative phosphorylation in flukes. It is formulated as an oral drench containing oxyclozanide only or in combination with levamisole hydrochloride or oxfendazole or as a powder to be incorporated in the feed. The recommended doses are 10 to 15 mg oxyclozanide/kg BW for cattle and 15 mg oxyclozanide/kg BW for sheep and goats. The application was amended to exclude sheep milk and goat tissues and milk.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Fasciola hepatica 2 Target ID: CHEMBL612860 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25771931	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Fascioliasis 5 Sources: https://goo.gl/hjMyxx	Curative		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Activity of oxyclozanide, nitroxynil, clorsulon and albendazole against adult triclabendazole-resistant Fasciola hepatica.	2001 Jun 9	11430684
Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi.	2002 Jun 3	12113305
Worm control practices and anthelmintic usage in traditional and dairy cattle farms in the southern highlands of Tanzania.	2003 May 15	12732466
Anthelmintic efficacy of genistein, the active principle of Flemingia vestita (Fabaceae): alterations in the free amino acid pool and ammonia levels in the fluke, Fasciolopsis buski.	2004 Dec	15464437
[Concentration in plasma and excretion in milk of lactating cows after oral administration of tribromsalan, oxyclozanide and bromofenofos].	2006 Dec	17228788
Analysis of the IgG antibody response against Paramphistomidae trematoda in naturally infected cattle. Application to serological surveys.	2006 Sep 10	16672179
[The investigation of short term efficiency of oxfendazole + oxyclozanide paste and tablet formulations against gastrointestinal nematodes in sheep].	2008	18645944
In Vitro Anthelmintic Activity of Baliospermum montanum Muell. Arg roots.	2008 Jan	20390101
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.	2009 Jul 14	19597541
Efficacy of oxyclozanide against the rumen fluke Calicophoron daubneyi in experimentally infected goats.	2009 May	18314360
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.	2009 Nov 13	19426989
The comparative efficacy of four anthelmintics against a natural acquired Fasciola hepatica infection in hill sheep flock in the west of Ireland.	2009 Oct 14	19556063
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.	2010 Feb 3	20128898
Determination of bithionol, bromophen, nitroxynil, oxyclozanide, and tribromsalan in milk with liquid chromatography coupled with tandem mass spectrometry.	2010 Jul-Aug	20922970

Patents

Sample Use Guides

In Vivo Use Guide

The recommended doses are 10 to 15 mg oxyclozanide/kg bw for cattle and 15 mg oxyclozanide/kg bw for sheep and goats

Route of Administration: Oral

In Vitro Use Guide

Oxyclozanide (5 mg/ml stock solution in DMSO) were tested by broth microdilution and disc diffusion assays in triplicate, adapted from established protocol. Broth microdilution was performed in triplicate in 96-well plates using Müller-Hinton broth (Becton Dickinson and Company, Franklin Lakes, NJ, USA). For testing MIC with daptomycin, the media was supplemented with CaCl2 at a final concentration of 50 μg/ml. The assay volume was 100 μl and twofold serial dilutions were carried out to get Oxyclozanide in the concentration range 0.0625–64 μg/ml. The bacterial concentration was adjusted to an initial OD600 of 0.03. After overnight incubation at 35°C, the absorbance was measured to determine antimicrobial activity. The minimum bactericidal concentration (MBC) was determined by plating 10 μl of culture volume from the MIC assay on Müller-Hinton agar and colony formation was examined after overnight incubation at 35°C. The lowest concentration at which colonies were not observed was regarded as the MBC.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:28:14 GMT 2023` Edited by `admin` on `Fri Dec 15 15:28:14 GMT 2023`
Record UNII	1QS9G4876X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

OXYCLOZANIDE

Official Name

English

ZANIL

Brand Name

English

OXYCLOZANIDE [MART.]

Common Name

English

3,3',5,5',6-PENTACHLORO-2'-HYDROXYSALICYLANILIDE

Systematic Name

English

ZANILOX

Brand Name

English

Oxyclozanide [WHO-DD]

Common Name

English

ICI-46683

Code

English

OXYCLOZANIDE [MI]

Common Name

English

DIPLIN

Brand Name

English

oxyclozanide [INN]

Common Name

English

ICI 46683

Code

English

Classification Tree Code System Code

WHO-VATC

QP52AG06