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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 of OXYCLOZANIDE

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
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

Curator's Comment: Oxyclozanide caused liver and brain toxicity at the highest tested doses.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Activity of oxyclozanide, nitroxynil, clorsulon and albendazole against adult triclabendazole-resistant Fasciola hepatica.
2001 Jun 9
Analysis of the IgG antibody response against Paramphistomidae trematoda in naturally infected cattle. Application to serological surveys.
2006 Sep 10
[The investigation of short term efficiency of oxfendazole + oxyclozanide paste and tablet formulations against gastrointestinal nematodes in sheep].
2008
In Vitro Anthelmintic Activity of Baliospermum montanum Muell. Arg roots.
2008 Jan
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.
2009 Jul 14
Efficacy of oxyclozanide against the rumen fluke Calicophoron daubneyi in experimentally infected goats.
2009 May
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.
2009 Nov 13
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
Unchanged triclabendazole kinetics after co-administration with ivermectin and methimazole: failure of its therapeutic activity against triclabendazole-resistant liver flukes.
2010 Feb 3
Determination of bithionol, bromophen, nitroxynil, oxyclozanide, and tribromsalan in milk with liquid chromatography coupled with tandem mass spectrometry.
2010 Jul-Aug
Patents

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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:28:14 UTC 2023
Record UNII
1QS9G4876X
Record Status Validated (UNII)
Record Version
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Name Type Language
OXYCLOZANIDE
INN   MART.   MI  
INN  
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
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
Code System Code Type Description
PUBCHEM
16779
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID50177312
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
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MERCK INDEX
m8327
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
OXYCLOZANIDE
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
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INN
2159
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
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ChEMBL
CHEMBL2105450
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
PRIMARY
EVMPD
SUB09561MIG
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
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SMS_ID
100000083282
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
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FDA UNII
1QS9G4876X
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
PRIMARY
NCI_THESAURUS
C66279
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
PRIMARY
ECHA (EC/EINECS)
218-904-0
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
PRIMARY
CAS
2277-92-1
Created by admin on Fri Dec 15 15:28:14 UTC 2023 , Edited by admin on Fri Dec 15 15:28:14 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY