| Size | Price | Stock | Qty |
|---|---|---|---|
| 500mg |
|
||
| Other Sizes |
|
| ln Vitro |
In saltwater, bithionol (0.1–10 mg/mL, 72 h) exhibits toxicity to fresh Paraamoebae parasites [1]. Adenylyl cyclase (AC) activity is inhibited by bithionol (0-100 μM) at IC50 value. Bithionol (50 and 100 μM, 0-10 min) decreases cAMP and almost inhibits sAC. In cells overexpressing 4-4 Cumulative impact, sAC boosts cAMP.
|
|---|---|
| ln Vivo |
In mice, bithionol exhibits moderate efficacy against immature H. nana (100 mg/kg/day, side wall powder for 12 days) [3].
|
| Animal Protocol |
Animal/Disease Models: Immature H. nana infected mice [3]
Doses: 100 mg/kg/day Route of Administration: Oral administration, 12 days after infection Experimental Results: 48% of mature H. nana eliminated. LD50: 760 mg/kg. |
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Bithionol is ... absorbed to a limited degree from the host digestive tract and detected in blood and especially in bile in which it is excreted from the body. Peak concentrations are found in bile within 2 hr following treatment. Blood concentrations of the drug are significantly lower than those found in bile. When (35)S-bithionol, (35)S-bithionol sulfoxide, or (35)S-bithionol sulfone were fed to rats, urinary excretion of the metabolites ... was very low. Bithionol sulfoxide was excreted mainly in the feces. More than 90% of biliary radioactivity was in the form of glucuronides of the 3 compounds with more than 70% of the glucuronides present as bithionol glucuronide. Metabolism / Metabolites When (35)S-bithionol sulfoxide was orally admin to rats, urine, feces & bile were collected. Eight metabolites were observed in the urine. Paper chromatography & chemical tests identified one of these as inorganic sulfate. A strong acid was identified as 3,5-dichloro-2-hydroxysulfonic acid. Two other cmpd were identified as bithionol sulfone & bithionol. In addition to these, 3 cmpd were identified as glucuronides of bithionol, bithionol sulfoxide, & bithionol sulfone. One other metabolite was not identified. Except for free bithionol sulfone, the same metabolites were found in bile as were present in urine. Quantitative differences, however, were large. The glucuronide of bithionol sulfone comprised 71% of (35)S in bile but only 16.5% in urine. /Bithionol sulfoxide/ When (35)S-bithionol, (35)S-bithionol sulfoxide, or (35)S-bithionol sulfone were fed to rats, urinary excretion of the metabolites ... was very low. ... More than 90% of biliary radioactivity was in the form of glucuronides of the 3 compounds with more than 70% of the glucuronides present as bithionol glucuronide. The sulfone was metabolized to catechol & guaiacol. /Bithionol and bithionol sulfone are major metabolites of bithionol sulfoxide/ |
| Toxicity/Toxicokinetics |
Interactions
Toxicity is moderately to markedly enhanced when bithionol is admin in combination with carbon tetrachloride, sodium antimonyl tartrate, emetine hydrochloride, hexachloroethane, or hexachloroparaxylene. Non-Human Toxicity Values LD50 Rat oral 1430 mg/kg LD50 Mouse oral 2100 mg/kg LD50 Mouse iv 18 mg/kg |
| References |
|
| Additional Infomation |
2,2'-thiobis(4,6-dichlorophenol) appears as white or grayish white crystalline powder with a very faint aromatic or phenolic odor. (NTP, 1992)
Bithionol is an aryl sulfide that is diphenyl sulfide in which each phenyl group is substituted at position 2 by hydroxy and at positions 3 and 5 by chlorine. A fungicide and anthelmintic, it was used in various topical drug products for the treatment of liver flukes, but withdrawn after being shown to be a potent photosensitizer with the potential to cause serious skin disorders. It has a role as an antiplatyhelmintic drug and an antifungal agrochemical. It is an aryl sulfide, an organochlorine pesticide, a dichlorobenzene, a polyphenol, a bridged diphenyl fungicide and a bridged diphenyl antifungal drug. Bithionol, formerly marketed as an active ingredient in various topical drug products, was shown to be a potent photosensitizer with the potential to cause serious skin disorders. Approvals of the NDA's for bithionol drug products were withdrawn on October 24, 1967 (see the Federal Register of October 31, 1967 (32 FR 15046)). Halogenated anti-infective agent that is used against trematode and cestode infestations. Mechanism of Action Bithionol interferes with the neuromuscular physiology of helminths /(the target species)/, impairs egg formation, and may cause the protective cuticle covering the worms to become defective. At the biochemical level, oxidative phosphorylation is inhibited, and the bithionol molecule can chelate iron so that it may inactivate iron-containing enzyme systems. /In the target species,/ bithionol treatment of adult worms in vivo decreases glycolytic and oxidative metabolism. Specifically, succinate oxidation is inhibited. Although the exact mode of action of bithionol is not known, it is suggested that it may depend on phenolic OH groups acting as acceptors of hydrogen that otherwise would enter into reactions associated with succinate oxidation. Interference of these reactions perhaps deprives the fluke of the necessary quantity of energy for maintenance of life. Therapeutic Uses Anti-Infective Agents, Local; Antiplatyhelmintic Agents Bithionol is used in treatment of paragonimiasis in a dosage of 30 to 50 mg/kg body wt, given by mouth on alternate days for 10 to 15 doses. In the treatment of clonorchiasis, the same dose has been given. Bithionol has also been used in a dose of up to 3 g daily on alternate days for 15 doses, in the treatment of fascioliasis. Doses of up to 60 mg/kg body wt, in 2 divided doses about 1 hr apart, have been given in tapeworm infection. Cerebral infection occurs in 0.8% of patients with pulmonary infection. In a group of 24 patients with cerebral infections, bithionol was effective in all in eliminating ova from the sputum & terminating the prodn of rusty sputum. However, in only 9 patients was it effective in control of cerebral symptoms, including loss of vision, frank meningitis, & one case of intradural abscess. The drug is given ... with meals to reduce the incidence of intensity of gastrointestinal symptoms. For more Therapeutic Uses (Complete) data for BITHIONOL (16 total), please visit the HSDB record page. |
| Molecular Formula |
C12H6CL4O2S
|
|---|---|
| Molecular Weight |
356.038
|
| Exact Mass |
353.884
|
| CAS # |
97-18-7
|
| Related CAS # |
Bithionol (sulfoxide);844-26-8
|
| PubChem CID |
2406
|
| Appearance |
White to off-white solid powder
|
| Density |
1.8±0.1 g/cm3
|
| Boiling Point |
444.7±45.0 °C at 760 mmHg
|
| Melting Point |
188°C
|
| Flash Point |
222.8±28.7 °C
|
| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.741
|
| LogP |
5.51
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
2
|
| Heavy Atom Count |
19
|
| Complexity |
282
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
JFIOVJDNOJYLKP-UHFFFAOYSA-N
|
| InChi Code |
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
|
| Chemical Name |
2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol
|
| Synonyms |
Bithionol CP 3438 Bitin CP3438 Lorothidol CP-3438
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ≥ 33 mg/mL (~92.68 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.84 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.84 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8087 mL | 14.0434 mL | 28.0867 mL | |
| 5 mM | 0.5617 mL | 2.8087 mL | 5.6173 mL | |
| 10 mM | 0.2809 mL | 1.4043 mL | 2.8087 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
|
|
|
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
