Oxyclozanide | CAS#2277-92-1 | anthelmintic

MedKoo Cat#: 461721 | Name: Oxyclozanide

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Oxyclozanide is a salicylanilide anthelmintic. Oxyclozanide is used in the treatment and control of fascioliasis in ruminants mainly domestic animals such as cattle, sheep, and goats. Oxyclozanide has exhibited antibacterial activity by disrupting cell integrity and reducing bacterial pathogenicity.

Chemical Structure

Oxyclozanide

CAS#2277-92-1

Theoretical Analysis

MedKoo Cat#: 461721

Name: Oxyclozanide

CAS#: 2277-92-1

Chemical Formula: C13H6Cl5NO3

Exact Mass: 398.8790

Molecular Weight: 401.45

Elemental Analysis: C, 38.90; H, 1.51; Cl, 44.15; N, 3.49; O, 11.96

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 260.00

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Synonym

Oxyclozanide; Diplin; ICI 46683; ICI-46683; ICI46683; Oxiclozanida; Zanilox;

IUPAC/Chemical Name

2,3,5-trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide

InChi Key

JYWIYHUXVMAGLG-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

OC1=C(Cl)C=C(Cl)C(Cl)=C1C(NC2=CC(Cl)=CC(Cl)=C2O)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Oxyclozanide is an orally active salicylanilide anthelmintic agent.

In vitro activity:

The MIC and MPC of oxyclozanide were determined from eighteen meticillin sensitive S. pseudintermedius (MSSP) isolates and eleven meticillin-resistant S. pseudintermedius (MRSP), as well as single isolates of Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Enterococcus faecalis. Oxyclozanide demonstrated in-vitro antibacterial activity against meticillin-resistant S. pseudintermedius. Reference: Vet Dermatol. 2019 Aug;30(4):314-e87. https://pubmed.ncbi.nlm.nih.gov/31062461/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	90.0	224.19

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 401.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Levinson MR, Blondeau JM, Rosenkrantz WS, Plowgian CB. The in vitro antibacterial activity of the anthelmintic drug oxyclozanide against common small animal bacterial pathogens. Vet Dermatol. 2019 Aug;30(4):314-e87. doi: 10.1111/vde.12755. Epub 2019 May 7. PMID: 31062461. 2. Maiden MM, Zachos MP, Waters CM. The ionophore oxyclozanide enhances tobramycin killing of Pseudomonas aeruginosa biofilms by permeabilizing cells and depolarizing the membrane potential. J Antimicrob Chemother. 2019 Apr 1;74(4):894-906. doi: 10.1093/jac/dky545. PMID: 30624737; PMCID: PMC6735725.

In vitro protocol:

In vivo protocol:

TBD

1: Gokbulut C, Yalinkilinc HS, Aksit D, Veneziano V. Comparative pharmacokinetics of levamisole-oxyclozanide combination in sheep and goats following per os administration. Can J Vet Res. 2014 Oct;78(4):316-20. PubMed PMID: 25356001; PubMed Central PMCID: PMC4170771. 2: Sanabria R, Moreno L, Alvarez L, Lanusse C, Romero J. Efficacy of oxyclozanide against adult Paramphistomum leydeni in naturally infected sheep. Vet Parasitol. 2014 Dec 15;206(3-4):277-81. doi: 10.1016/j.vetpar.2014.09.022. Epub 2014 Oct 7. PubMed PMID: 25458118. 3: Rajamuthiah R, Fuchs BB, Conery AL, Kim W, Jayamani E, Kwon B, Ausubel FM, Mylonakis E. Repurposing salicylanilide anthelmintic drugs to combat drug resistant Staphylococcus aureus. PLoS One. 2015 Apr 21;10(4):e0124595. doi: 10.1371/journal.pone.0124595. eCollection 2015. PubMed PMID: 25897961; PubMed Central PMCID: PMC4405337. 4: Kang YJ, Wakabayashi C, Kim KH. Antihelminthic potential of quinacrine and oxyclozanide against gill parasite Microcotyle sebastis in black rockfish Sebastes schlegeli. Dis Aquat Organ. 2016 May 26;119(3):259-63. doi: 10.3354/dao02997. PubMed PMID: 27225210. 5: Whelan M, Chirollo C, Furey A, Cortesi ML, Anastasio A, Danaher M. Investigation of the persistence of levamisole and oxyclozanide in milk and fate in cheese. J Agric Food Chem. 2010 Dec 8;58(23):12204-9. doi: 10.1021/jf102725b. Epub 2010 Nov 8. PubMed PMID: 21058728. 6: Sakamoto M, Takeba K, Sasamoto T, Kusano T, Hayashi H, Kanai S, Kanda M, Nagayama T. Determination of bithionol, bromophen, nitroxynil, oxyclozanide, and tribromsalan in milk with liquid chromatography coupled with tandem mass spectrometry. J AOAC Int. 2010 Jul-Aug;93(4):1340-6. PubMed PMID: 20922970. 7: Oakley GA, Cockshott ID, Owen B. Acceptability of levamisole and oxyclozanide for the post parturient ewe and newborn lamb. Vet Rec. 1984 Apr 14;114(15):381-2. PubMed PMID: 6730244. 8: Paraud C, Gaudin C, Pors I, Chartier C. Efficacy of oxyclozanide against the rumen fluke Calicophoron daubneyi in experimentally infected goats. Vet J. 2009 May;180(2):265-7. doi: 10.1016/j.tvjl.2008.01.002. Epub 2008 Mar 7. PubMed PMID: 18314360. 9: Corba J, Pacenovský J, Krupicer I, Breza M, Popovic S, Reisz T. [Effectiveness of oxyclozanide in cattle naturally invaded by Liorchis scotiae trematoda]. Vet Med (Praha). 1976;21(8):461-5. Slovak. PubMed PMID: 828347. 10: Björk P, Källberg E, Wellmar U, Riva M, Olsson A, He Z, Törngren M, Liberg D, Ivars F, Leanderson T. Common interactions between S100A4 and S100A9 defined by a novel chemical probe. PLoS One. 2013 May 8;8(5):e63012. doi: 10.1371/journal.pone.0063012. Print 2013. PubMed PMID: 23667563; PubMed Central PMCID: PMC3648463. 11: Khan AR, Akhtar MJ, Mahmood R, Ahmed SM, Malook S, Iqbal M. LC assay method for oxfendazole and oxyclozanide in pharmaceutical preparation. J Pharm Biomed Anal. 2000 Feb;22(1):111-4. PubMed PMID: 10727129. 12: Georgiev B, Gruev A. [Effectiveness of levamisole and oxyclozanide in paramphistomiasis in sheep and cattle]. Vet Med Nauki. 1979;16(3):45-51. Bulgarian. PubMed PMID: 524749. 13: Edwards SR, Campbell AJ, Sheers M, Moore RJ, Montague PE. Studies of the effect of diamphenethide and oxyclozanide on the metabolism of Fasciola hepatica. Mol Biochem Parasitol. 1981 Apr;2(5-6):323-38. PubMed PMID: 7242570. 14: Arafa WM, Shokeir KM, Khateib AM. Comparing an in vivo egg reduction test and in vitro egg hatching assay for different anthelmintics against Fasciola species, in cattle. Vet Parasitol. 2015 Nov 30;214(1-2):152-8. doi: 10.1016/j.vetpar.2015.09.023. Epub 2015 Sep 30. PubMed PMID: 26455573. 15: Fujinuma K, Takeba K, Kamata K. [Concentration in plasma and excretion in milk of lactating cows after oral administration of tribromsalan, oxyclozanide and bromofenofos]. Shokuhin Eiseigaku Zasshi. 2006 Dec;47(6):249-53. Japanese. PubMed PMID: 17228788. 16: Coles GC, Stafford KA. Activity of oxyclozanide, nitroxynil, clorsulon and albendazole against adult triclabendazole-resistant Fasciola hepatica. Vet Rec. 2001 Jun 9;148(23):723-4. PubMed PMID: 11430684. 17: Dinç E, Kanbur M. Spectrophotometric multicomponent resolution of a veterinary formulation containing oxfendazole and oxyclozanide by multivariate calibration-prediction techniques. J Pharm Biomed Anal. 2002 May 15;28(3-4):779-88. PubMed PMID: 12008158. 18: Maffei Facino R, Carini M, Genchi C. Decrease in hepatic microsomal UDP-glucuronosyl-transferase activity in rats and cattle with fascioliasis: impaired in vitro glucuronidation of oxyclozanide. Toxicol Lett. 1985 Jul;26(1):65-71. PubMed PMID: 3927525. 19: Romaniuk K, Lipiński Z. [Evaluation of the effectiveness of oxyclozanide (Zanil-Biowet and Zanil-ICI) and bromphenophos (Acedist IST) in the treatment of fascioliasis in cattle]. Wiad Parazytol. 1982;28(3-4):405-9. Polish. PubMed PMID: 6305038. 20: Ma Y, He YH, Deng P, Zhang SY, Ding YY, Zhang ZJ, Zhang BQ, An JX, Wang YR, Liu YQ. Repurposing Salicylamides to Combat Phytopathogenic Bacteria and Induce Plant Defense Responses. Chem Biodivers. 2023 Nov;20(11):e202300998. doi: 10.1002/cbdv.202300998. Epub 2023 Oct 27. PMID: 37755070.