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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
Structure of BITHIONOLOXIDE

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

HIDE SMILES / InChI

Molecular Formula C12H6Cl4O3S
Molecular Weight 372.051
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 It has been used for veterinary applications but has more recently been superseded by modern anthelmintic drugs.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[A Study On The Chemotherapy In Clonorchiasis: Report 1. An Experimental Study On Chemotherapy With Dithiazanine Iodide And Bithionol Sulfoxide In Clonorchiasis].
1965 Jun
Liquid chromatographic determination of depletion of bithionol sulfoxide and its two major metabolites in bovine milk.
1987 Sep-Oct
Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi.
2002 Jun 3
In vitro toxicity of bithionol and bithionol sulphoxide to Neoparamoeba spp., the causative agent of amoebic gill disease (AGD).
2010 Sep 17
Patents

Sample Use Guides

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
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%.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:47:14 GMT 2023
Edited
by admin
on Sat Dec 16 17:47:14 GMT 2023
Record UNII
6PL3DO2B30
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BITHIONOLOXIDE
INN  
INN  
Official Name English
NSC-523910
Code English
bithionoloxide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
Code System Code Type Description
EVMPD
SUB05858MIG
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
NSC
523910
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL1603949
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
FDA UNII
6PL3DO2B30
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
NCI_THESAURUS
C78040
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
PUBCHEM
68939
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
SMS_ID
100000086342
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
INN
5289
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID5046225
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
CAS
844-26-8
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-679-2
Created by admin on Sat Dec 16 17:47:14 GMT 2023 , Edited by admin on Sat Dec 16 17:47:14 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY