Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H6Cl4O2S |
Molecular Weight | 356.052 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(SC2=C(O)C(Cl)=CC(Cl)=C2)C=C(Cl)C=C1Cl
InChI
InChIKey=JFIOVJDNOJYLKP-UHFFFAOYSA-N
InChI=1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
Molecular Formula | C12H6Cl4O2S |
Molecular Weight | 356.052 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04813 | https://goo.gl/7Qnwi7 | https://www.ncbi.nlm.nih.gov/pubmed/26961873 | https://www.ncbi.nlm.nih.gov/pubmed/5567745 | https://www.ncbi.nlm.nih.gov/pubmed/23990907
Curator's Comment: description was created based on several sources, including
https://www.drugbank.ca/drugs/DB04813 | https://goo.gl/7Qnwi7 | https://www.ncbi.nlm.nih.gov/pubmed/26961873 | https://www.ncbi.nlm.nih.gov/pubmed/5567745 | https://www.ncbi.nlm.nih.gov/pubmed/23990907
Bithionol is a synthetic sulfanediyl-bis-dichlorphenol), potent photosensitizer with the potential to cause serious skin disorders, formerly marketed as an active ingredient in various topical drug products. Bithionol has antibacterial and anthelmintic properties along with algaecide activity. Bithionol has been shown to be a potent inhibitor of soluble adenylyl cyclase (sAC, Adenylate cyclase type 10 ), an intracellular enzyme important in the catalysis of ATP to cAMP. Bithionol is the first known sAC inhibitor to act through the bicarbonate binding site via a mostly allosteric mechanism. Bithionol is used for treatment of tapeworm infections of dogs, cats, and poultry and for tapeworm and rumen fluke infections of sheep, horses, cattle, and goats.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5854 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26961873 |
4.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Actamer Approved UseUnknown |
Doses
Dose | Population | Adverse events |
---|---|---|
1 % 1 times / day single, topical Studied dose Dose: 1 %, 1 times / day Route: topical Route: single Dose: 1 %, 1 times / day Sources: |
healthy, 22 years n = 1 Health Status: healthy Age Group: 22 years Sex: F Population Size: 1 Sources: |
Other AEs: Contact dermatitis... |
2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: |
unhealthy, mean age 35 years n = 8 Health Status: unhealthy Condition: intestinal capillariasis Age Group: mean age 35 years Sex: M+F Population Size: 8 Sources: |
Other AEs: Abdominal pain aggravated... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Contact dermatitis | 1 % 1 times / day single, topical Studied dose Dose: 1 %, 1 times / day Route: topical Route: single Dose: 1 %, 1 times / day Sources: |
healthy, 22 years n = 1 Health Status: healthy Age Group: 22 years Sex: F Population Size: 1 Sources: |
|
Abdominal pain aggravated | 37.5% | 2.4 g 1 times / day multiple, oral Studied dose Dose: 2.4 g, 1 times / day Route: oral Route: multiple Dose: 2.4 g, 1 times / day Sources: |
unhealthy, mean age 35 years n = 8 Health Status: unhealthy Condition: intestinal capillariasis Age Group: mean age 35 years Sex: M+F Population Size: 8 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs. | 1992 Sep |
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Efficacy of 101 antimicrobials and other agents on the development of Cryptosporidium parvum in vitro. | 1996 Dec |
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Hydrogen peroxide induced stress in human keratinocytes and its effect on bithionol toxicity. | 2001 Aug-Oct |
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Search of chemical scaffolds for novel antituberculosis agents. | 2005 Apr |
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Evaluation of bithionol as a bath treatment for amoebic gill disease caused by Neoparamoeba spp. | 2007 Mar 31 |
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An evaluation of the effects of photoactivation of bithionol, amiodarone and chlorpromazine on human keratinocytes in vitro. | 2007 Oct |
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Novel inhibitors complexed with glutamate dehydrogenase: allosteric regulation by control of protein dynamics. | 2009 Aug 21 |
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Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening. | 2009 Jul 14 |
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Diphyllobothriasis associated with eating raw pacific salmon. | 2009 Jun |
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[Phosphatases of cestodes Bothriocephalus scorpii and influence of some anthelmintic preparations on activities of these enzymes]. | 2009 Mar-Apr |
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Evaluation of marked rise in fecal egg output after bithionol administration to horse and its application as a diagnostic marker for equine Anoplocephala perfoliata infection. | 2009 May |
|
Identification of known drugs that act as inhibitors of NF-kappaB signaling and their mechanism of action. | 2010 May 1 |
|
In vitro toxicity of bithionol and bithionol sulphoxide to Neoparamoeba spp., the causative agent of amoebic gill disease (AGD). | 2010 Sep 17 |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
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An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide. | 2012 Jan 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Bithionol is given orally at a dose of 30 to 50 mg per kg of body weight on alternate days for ten to fifteen doses for the treatment of fascioliasis and paragonimiasis in adults and children.
After oral administration of single bithionol doses of 30 mg/kg body weight to
healthy test persons (fasting, number not stated) no effects were observed, single oral doses of 50 mg/kg body weight caused diarrhoea and 150 mg/kg body weight prolonged diarrhoea, nausea and abdominal pains
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24495391
Cytotoxic effect of BT (Bithionol) was evaluated against a panel of ovarian cancer cell lines (A2780 & A2780-CDDP OVACAR-3, SKOV-3, IGROV-1, and IGROV-1CDDP). A 20 mM stock of BT was prepared in DMSO and all the working dilutions were prepared in DMEM media. Ovarian cancer cell lines (5 × 103 cells/well) were plated into 96-well flat bottom plates (Corning, Inc., Corning, NY) and incubated for overnight. Cells were treated with different concentrations of BT ranging from 0.178 μM to 400 μM and further incubated for 48 hrs or 72 hrs. At least 4–6 hrs before the end of treatment time, presto blue reagent was added and incubated for total of 48 or 72 hrs and fluorescence measured (540 nm excitation/590 nm emissions). DMSO concentration was corrected to 1% in all wells.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:00:09 UTC 2023
by
admin
on
Fri Dec 15 15:00:09 UTC 2023
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Record UNII |
AMT77LS62O
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Record Status |
Validated (UNII)
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Record Version |
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WHO-ATC |
P02BX01
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WHO-VATC |
QD10AB01
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EPA PESTICIDE CODE |
64201
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CFR |
21 CFR 700.11
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WHO-ATC |
D10AB01
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NCI_THESAURUS |
C28394
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WHO-VATC |
QP52AG07
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C77030
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SUB05857MIG
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DB04813
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202-565-0
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m2577
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201
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D001735
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AMT77LS62O
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6380
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DTXSID9021342
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97-18-7
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100000086322
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CHEMBL290106
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BITHIONOL
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3032
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bithionol
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47129
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2406
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3131
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ACTIVE MOIETY |