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| Targets |
The molecular targets of Phenithionate have not been extensively characterized in the published literature. Based on its structural features, particularly the presence of the thiocarbamate moiety and the nitro-substituted diphenylamine core, potential targets include enzymes involved in oxidative stress response and xenobiotic metabolism. Thiocarbamates are known to interact with cytochrome P450 enzymes, particularly CYP2E1 and CYP3A4, through coordination to the heme iron or through formation of reactive intermediates. The nitro group may undergo bioreduction to generate reactive species that can alkylate proteins or DNA. Additionally, the compound's diphenylamine structure suggests possible interactions with various receptors or enzymes through hydrophobic and π-π stacking interactions. However, specific target identification would require systematic screening against panels of enzymes, receptors, and other biological targets using techniques such as affinity chromatography, thermal shift assays, or computational docking studies.
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| ln Vitro |
In vitro biological activity data for Phenithionate are limited in the available scientific literature. However, as a thiocarbamate derivative, the compound may exhibit enzyme inhibitory activity against certain hydrolases and transferases. Thiocarbamates have been reported to inhibit acetylcholinesterase and butyrylcholinesterase through carbamoylation of the active site serine residue, with IC50 values typically in the micromolar range. The presence of the nitrophenyl group may enhance electrophilicity and reactivity toward biological nucleophiles. Some diphenylamine derivatives have demonstrated antioxidant and anti-inflammatory activities in cell-based assays, protecting against oxidative damage induced by reactive oxygen species. The compound's ability to act as a metal chelator, similar to other thiocarbamates, could contribute to its biological effects by modulating metal-dependent enzyme activities. Specific in vitro assays including enzyme inhibition studies, cell viability tests, and antioxidant activity measurements would be needed to fully characterize its biological profile.
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| ln Vivo |
In vivo pharmacological data for Phenithionate are not well-documented. As a chemical intermediate primarily used for organic synthesis, it has not been developed as a therapeutic candidate for animal model studies. However, structurally related thiocarbamate derivatives have been evaluated in animal models for various pharmacological activities including anticonvulsant, anti-inflammatory, and antimicrobial effects. For example, some thiocarbamates have shown protection against seizures in rodent models at doses of 10-100 mg/kg. Others have demonstrated anti-inflammatory activity in carrageenan-induced paw edema models. The nitro group in Phenithionate raises the possibility of bioreductive activation in hypoxic tissues, which could be exploited for targeted drug delivery to tumors or inflammatory sites. Nevertheless, the absence of specific in vivo data for this compound limits conclusions about its pharmacokinetic and pharmacodynamic properties in animal systems.
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| Enzyme Assay |
For in vitro enzyme inhibition assays with thiocarbamate compounds like Phenithionate, the following general protocol is employed: the target enzyme (e.g., acetylcholinesterase or a cytochrome P450 isoform) is incubated with the test compound at concentrations ranging from 0.01 to 100 μM in an appropriate buffer system (e.g., 50 mM phosphate buffer, pH 7.4) at 25-37°C for 10-30 minutes. For acetylcholinesterase assays, the substrate acetylthiocholine and the chromogenic reagent DTNB are added, and the rate of thiocholine production is monitored spectrophotometrically at 412 nm. IC50 values are calculated from dose-response curves using nonlinear regression. For P450 inhibition assays, a fluorogenic or luminogenic substrate specific for the P450 isoform is used, with the reaction initiated by addition of NADPH, and fluorescence or luminescence is measured after incubation. Positive controls such as donepezil for AChE or ketoconazole for CYP3A4 are included in each experiment to validate the assay system.
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| Cell Assay |
For in vitro cell-based assays with compounds like Phenithionate, the following typical protocol is used: mammalian cells (e.g., HepG2 liver cells or HEK293 kidney cells) are cultured in DMEM or RPMI-1640 medium containing 10% fetal bovine serum and antibiotics at 37°C in a 5% CO2 atmosphere. Cells are seeded in 96-well plates at 5,000-15,000 cells per well and allowed to attach overnight. The test compound is dissolved in DMSO and diluted in culture medium to final concentrations ranging from 0.1 to 200 μM (final DMSO ≤ 0.1%). After 24-72 hours of treatment, cell viability is assessed using the MTT assay: MTT (0.5 mg/mL) is added and incubated for 4 hours, followed by addition of solubilization solution and measurement at 570 nm. For cytotoxicity screening, the lactate dehydrogenase (LDH) release assay can be used to measure membrane integrity. For assessment of oxidative stress, cells can be treated with the compound and then loaded with the fluorescent probe DCFH-DA to measure reactive oxygen species production.
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| Animal Protocol |
For in vivo animal studies with thiocarbamate compounds, the following general protocol is followed: male or female SPF-grade mice or rats (6-8 weeks old, 20-25 g for mice or 180-220 g for rats) are used. The test compound is formulated in a suitable vehicle (e.g., 0.5% methylcellulose, PEG400, or saline with 1% Tween 80) and administered via oral gavage, intraperitoneal injection, or intravenous injection at doses typically ranging from 1 to 100 mg/kg. For acute toxicity studies, a single dose is administered and animals are observed for 14 days with monitoring of body weight, food consumption, and clinical signs. For efficacy studies in disease models (e.g., inflammation, infection, or tumor models), the compound is administered daily for 7-21 days. Blood samples are collected at various time points via tail vein or retro-orbital puncture for PK analysis. At the end of the study, animals are euthanized and major organs (liver, kidney, heart, lung, brain) are harvested for histopathological examination.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Phenithionate have not been formally characterized. Based on its physicochemical characteristics (molecular weight 365.4 g/mol, predicted LogP ~4-5 due to the aromatic and thiocarbamate groups), the compound is expected to have high lipophilicity, which may limit aqueous solubility but favor membrane permeability and oral absorption. The thiocarbamate moiety is susceptible to hydrolysis by esterases and carboxylesterases, potentially generating a thiol and a carbamate that may undergo further metabolism. The nitro group can be reduced by nitroreductases to the corresponding amine, which may be further metabolized through acetylation or glucuronidation. The compound is predicted to have high plasma protein binding (>90%) due to its lipophilic nature. Metabolism is expected to occur primarily in the liver via cytochrome P450-mediated oxidation and phase II conjugation reactions. The predicted half-life is 1-3 hours based on structural analogs. Comprehensive PK studies are needed to determine actual absorption, distribution, metabolism, and elimination parameters.
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| Toxicity/Toxicokinetics |
The toxicological profile of Phenithionate has not been systematically evaluated in the literature. However, thiocarbamate compounds generally require careful toxicity assessment due to potential hepatotoxicity, neurotoxicity, and reproductive toxicity. The presence of the nitro group is a structural alert for mutagenicity and genotoxicity, as nitroarenes can undergo metabolic activation to reactive intermediates that form DNA adducts. Some thiocarbamates have been reported to cause skin sensitization and irritation. Acute oral toxicity in rats for structurally similar thiocarbamates is typically in the range of 200-2000 mg/kg. The compound should be handled with appropriate safety precautions in a well-ventilated fume hood with personal protective equipment. For any therapeutic development, comprehensive toxicology studies including Ames test for mutagenicity, chromosome aberration test for clastogenicity, and 28-day repeat-dose toxicity study in rodents would be required.
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| Additional Infomation |
Phenithionate is a chemical intermediate used in organic synthesis and has been assigned MeSH Unique ID C037013. Its CAS registry number is 83538-74-3 and it has the molecular formula C19H15N3O3S. The compound is also known as Carbamothioic acid, (4-((4-nitrophenyl)amino)phenyl)-, O-phenyl ester. It belongs to the diphenylamine analogs and derivatives category. The compound's diphenylamine core and thiocarbamate functionality suggest potential applications in materials science, particularly in the development of organic electronic materials or as a precursor for functional dyes. Future research could explore its reactivity in cross-coupling reactions, its potential as a building block for pharmaceutical intermediates, and its biological activities through systematic screening against various therapeutic targets.
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| Molecular Formula |
C19H15N3O3S
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| Molecular Weight |
365.4057
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| Exact Mass |
365.083
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| CAS # |
83538-74-3
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| PubChem CID |
5487655
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| Appearance |
Typically exists as solid at room temperature
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| Density |
1.388g/cm3
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| Index of Refraction |
1.723
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| LogP |
6.076
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
26
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| Complexity |
485
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[O-][N+](C1C=CC(NC2C=CC(NC(OC3C=CC=CC=3)=S)=CC=2)=CC=1)=O
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| InChi Key |
IEACVJXGZMTIIW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C19H15N3O3S/c23-19(26)21-18-11-8-15(12-17(18)13-4-2-1-3-5-13)20-14-6-9-16(10-7-14)22(24)25/h1-12,20H,(H2,21,23,26)
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| Chemical Name |
[4-(4-nitroanilino)-2-phenylphenyl]carbamothioic S-acid
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7367 mL | 13.6833 mL | 27.3665 mL | |
| 5 mM | 0.5473 mL | 2.7367 mL | 5.4733 mL | |
| 10 mM | 0.2737 mL | 1.3683 mL | 2.7367 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.
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