Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H6Cl4O3S |
Molecular Weight | 372.051 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(C=C(Cl)C=C1Cl)[S+]([O-])C2=C(O)C(Cl)=CC(Cl)=C2
InChI
InChIKey=RPAJWWXZIQJVJF-UHFFFAOYSA-N
InChI=1S/C12H6Cl4O3S/c13-5-1-7(15)11(17)9(3-5)20(19)10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
Bithionol sulfoxide is an effective cestocide, and also used as a fasciolicide, usually in combination with other compounds because of its poor efficiency against immature flukes. It has also demonstrated efficacy in vitro as an antiprotozoal agent effective against species causing amoebic gill disease in fish. It has been used for veterinary applications but has more recently been superseded by modern anthelmintic drugs.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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[A Study On The Chemotherapy In Clonorchiasis: Report 1. An Experimental Study On Chemotherapy With Dithiazanine Iodide And Bithionol Sulfoxide In Clonorchiasis]. | 1965 Jun |
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Liquid chromatographic determination of depletion of bithionol sulfoxide and its two major metabolites in bovine milk. | 1987 Sep-Oct |
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Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi. | 2002 Jun 3 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7338961
Three healthy volunteers received an oral dose of 0.5 g of Bithionol sulfoxide. The volunteers provided 20 mL urine samples at 12, 24, and 48 hours after administration. Bithionol sulphoxide was identified in beta-glucuronidase treated urine corresponding to 15.9 % of the administered dose at 48 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21133325
Neoparamoeb spp. were isolated from the gills of AGD-affected Atlantic salmon. Amoebae were allowed to adhere to Petri dishes for approximately 2 hours at 18 deg-C before being washed with seawater and then allowed to re-adhere to Petri dishes overnight at 18 deg-C. Adherent cells were removed by addition of 1 mL Hanks balanced salts trypsin EDTA, washed with seawater and concentrated. Live amoeba were determined by staining with 0.5% trypan blue-seawater 1:1 mix and counting with a hemocytometer. For the in vitro toxicity assay, live amoebae that were adhered to the flat bottom, 96 well microtitre plates with a density of approximately 10,000 cells in 150 micro-L per well were allowed to adhere for 1.5 hours at 18 deg-C and then exposed to different treatments. Test solutions were aerated and brought to 18 deg-C; amoebae were exposed to either bithionol or bithionol sulphoxide at 0, 0.1, 0.5, 1.0, 5.0, 0r 10.0 mg/L in triplicate and repeated 8 times over 72 hours. The number of live amoebae was determined at 0, 24, 48, and 72 hours. Bithionol sulphoxide reduced amoebae numbers significantly when compared to the seawater control at all concentrations and time points. When treated with 10 mg/L of bithionol sulphoxide there were a 57% relative reduction amoebae compared to seawater within the first 24 hours. After 72 hours the relative reduction was 99%.
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C250
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ACTIVE MOIETY