Bithionol
Product Information
Molecular Formula
C12H6Cl4O2S
Molecular Weight
356.05
Description
Bithionol is a clinically approved anti-parasitic drug. It has been shown to inhibit solid tumor growth in several preclinical cancer models. It caused dose-dependent cytotoxicity against all ovarian cancer cell lines.
Synonyms
Actamer; Bitin; CP 3438; CP-3438; CP3438; Lorothidol; NSC 47129; NSC-47129; NSC47129
IUPAC Name
2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol
SMILES
C1=C(C=C(C(=C1Cl)O)SC2=CC(=CC(=C2O)Cl)Cl)Cl
InChI
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
InChI Key
JFIOVJDNOJYLKP-UHFFFAOYSA-N
Boiling Point
444.7°C at 760 mmHg
Melting Point
188°C
Purity
>98%
Density
1.61 g/cm3
Solubility
Soluble in DMSO (20mg/mL)
Appearance
White to Off-white Solid
Application
Bithionol is one of the biocides commonly used in metalworking fluids.
Storage
Store at -20°C
LogP
log Kow = 5.91 (est)
Vapor Pressure
1.1e-09 mmHg at 99 °F
Henry's Law Constant
1.0X10-13 atm-cu m/mol at 25 °C (est)
Decomposition
When heated to decomposition it emits very toxic fumes of /hydrogen chloride and sulfur oxides.
Dissociation Constants
4.82
Odor
Odorless or with slight aromatic or phenolic odor
Related CAS
844-26-8 (sulfoxide)
Safety Information
Hazards
H300:
Fatal if swallowed.
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Fatal if swallowed.
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Precautionary Statement
P264:
Wash thoroughly after handling.
P270:
Do not eat, drink or smoke when using this product.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310+P330:
IF SWALLOWED:
Immediately call a POISON CENTER or doctor/physician.
Rinse mouth.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Wash thoroughly after handling.
P270:
Do not eat, drink or smoke when using this product.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310+P330:
IF SWALLOWED:
Immediately call a POISON CENTER or doctor/physician.
Rinse mouth.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Computed Properties
XLogP3
5.8
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
355.881311 g/mol
Monoisotopic Mass
353.884261 g/mol
Topological Polar Surface Area
65.8Ų
Heavy Atom Count
19
Formal Charge
0
Complexity
282
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-10980756-B1 | Methods of treatment | 2020-03-16 |
| WO-2021113419-A1 | Compositions having pesticidal utility and processes related thereto | 2019-12-06 |
| WO-2021107110-A1 | Benzimidazole compound or salt thereof, agricultural and horticultural insecticidal and acaricidal agent comprising said compound, and method for using said insecticidal and acaricidal agent | 2019-11-28 |
| WO-2021107113-A1 | Benzimidazole compound or salts thereof, agricultural and horticultural insecticide/acaricide containing said compound, and method for using same | 2019-11-28 |
| WO-2021105091-A1 | Novel heteroaryl-triazole compounds as pesticides | 2019-11-25 |
| US-2021156767-A1 | Device for extracting a molecule of interest from a sample matrix, and associated methods | 2019-11-22 |
| WO-2021099303-A1 | Novel heteroaryl-triazole compounds as pesticides | 2019-11-18 |
| WO-2021094594-A1 | Soil wetter composition | 2019-11-13 |
| US-2021138066-A1 | Remote-controlled image-guided drug delivery via ultrasound-modulated molecular diffusion | 2019-11-08 |
| WO-2021086044-A1 | Novel compound for crop protectant | 2019-10-29 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 35435491 | 2022-07-01 | Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation | Archives of toxicology |
| 33352258 | 2021-03-01 | In vitro screening for chemical inhibition of the iodide recycling enzyme, iodotyrosine deiodinase | Toxicology in vitro : an international journal published in association with BIBRA |
| 32284327 | 2020-05-22 | Symmetrically substituted dichlorophenes inhibit N-acyl-phosphatidylethanolamine phospholipase D | The Journal of biological chemistry |
| 22898086 | 2012-10-01 | A screen for modulators of large T antigen's ATPase activity uncovers novel inhibitors of Simian Virus 40 and BK virus replication | Antiviral research |
| 22335786 | 2012-05-09 | Chemical evolution of autotaxin inhibitors | Chemical reviews |
| 22342964 | 2012-05-01 | Biochemical and structural characterization of Plasmodium falciparum glutamate dehydrogenase 2 | Molecular and biochemical parasitology |
| 22015988 | 2012-01-05 | An improved thyroid hormone reporter assay to determine the thyroid hormone-like activity of amiodarone, bithionol, closantel and rafoxanide | Toxicology letters |
| 22489155 | 2012-01-01 | The hypoglycemic effect of the kelp on diabetes mellitus model induced by alloxan in rats | International journal of molecular sciences |
| 22194678 | 2011-12-01 | Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps) | PLoS computational biology |
| 21909440 | 2011-09-01 | Efficacy and safety of artemether in the treatment of chronic fascioliasis in Egypt: exploratory phase-2 trials | PLoS neglected tropical diseases |
