| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
2-Chlorophenothiazine targets multiple human and microbial proteins. Its primary human targets include NADPH oxidase 1 (NOX1), with an IC50 of 253.5 nM, and the cholinesterases (AChE and BuChE), with IC50s of 7400.0 nM and 19200.0 nM, respectively. It also interacts with the amyloid-beta A4 protein (APP) and tubulin (TUBB2B). For microbial targets, it shows activity against Mycobacterium tuberculosis and Mycolicibacterium smegmatis.
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| ln Vitro |
In vitro, 2-Chlorophenothiazine demonstrates potent inhibition of NOX1 with an IC50 of 253.5 nM and blocks Ebola virus entry with an AC50 of 39.81 uM. It exhibits dual cholinesterase inhibitory activity with higher selectivity for AChE. The compound has antioxidant properties, showing 76.4% DPPH free radical scavenging inhibition. It displays weak antiproliferative effects on K562 leukemia cells (IC50 > 100,000.0 nM) but shows moderate cytotoxicity against human SH-SY5Y neuroblastoma cells, reducing viability by 63.3% at 50 uM after 24 hours. Against SARS-CoV-2, it inhibits the 3CL-Pro protease by 16.02% at 20 uM. Its derivatives show enhanced activity against gastric cancer (MGC-803, IC50 0.5 uM; MKN28, MKN45) and leukemia (K-562, IC50 0.8 uM) cells.
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| ln Vivo |
In vivo, 2-Chlorophenothiazine serves as a valuable probe for studying the metabolism of phenothiazine drugs. It is identified as a major in vivo N-oxidation metabolite of Chlorpromazine and Promethazine. In animal models of Alzheimer's disease, its derivatives have demonstrated neuroprotective effects by reducing inflammatory markers and increasing neuroprotective factors. In cancer studies, derivatives of this compound have shown the ability to inhibit cell migration and enhance the efficacy of chemotherapy agents like carboplatin in combination treatments.
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| Enzyme Assay |
Non-cellular biochemical assays for 2-Chlorophenothiazine typically involve enzyme inhibition studies. For NOX1 inhibition, a luminol-based chemiluminescence assay is used. For cholinesterases, a colorimetric Ellman's assay is performed using acetylthiocholine iodide as a substrate; the reaction with 5,5'-dithiobis-(2-nitrobenzoic acid) (DTNB) produces a yellow color measured at 405 nm. The DPPH radical scavenging assay involves mixing the compound with a DPPH methanolic solution and measuring absorbance at 517 nm after incubation.
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| Cell Assay |
Cell-based assays for 2-Chlorophenothiazine are conducted using various cell lines. Cytotoxicity is typically assessed via MTT or Calcein-AM assays. For example, SH-SY5Y cells are seeded in 96-well plates and treated with 0-100 uM of the compound for 24 hours before MTT addition. For antiviral studies, SARS-CoV-2 3CL-Pro inhibition is tested in VERO-6 cells. For anticancer evaluations, cell lines such as MGC-803 or K-562 are treated with compound derivatives for 48-72 hours, followed by viability assessment via MTT assay. Cell migration is evaluated using a wound-healing or transwell assay.
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| Animal Protocol |
Animal studies for 2-Chlorophenothiazine are primarily focused on its metabolism and as a scaffold for new drug derivatives. In a classic metabolic study in rats, Chlorpromazine is administered and urine is collected; 2-Chlorophenothiazine is isolated and identified as a major metabolite via chromatographic separation. For anti-inflammatory assessment, derivatives of 2-chlorophenothiazine are screened against Carrageenin-induced paw edema in albino rats. In an Alzheimer's model, a derivative is administered orally to mice, after which brain tissues are collected for biochemical analysis of inflammatory markers.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic data for 2-Chlorophenothiazine are limited as it is an intermediate rather than a final drug. However, as a metabolite of chlorpromazine, it is formed via N-oxidation in the liver. The compound is a solid at room temperature with good solubility in organic solvents like DMSO (55 mg/mL) and ethanol, but poor solubility in water. It is stored at room temperature as a powder for up to 3 years.
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| Toxicity/Toxicokinetics |
2-Chlorophenothiazine is classified with a WGK Germany hazard class of 3. Phototoxic and photogenotoxic effects have been documented: in a photo-micronucleus test using V79 cells, it was identified as a photogenotoxin. It is a known skin and eye irritant. It has a relatively low acute oral toxicity (LD50 > 1,000 mg/kg in rats). General safety precautions suggest that it is a combustible solid and should be kept away from strong oxidizing agents and light sources due to photodegradation potential.
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| References | |
| Additional Infomation |
Other information: 2-Chlorophenothiazine has a purity of ≥98% from commercial sources and a melting point range of 196-199degC. It is a white to off-white crystalline solid with the RTECS number SN7580000. Its primary value in research is as a fundamental scaffold for developing novel pharmaceuticals, particularly in the fields of oncology and neurology.
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| Molecular Formula |
C12H8CLNS
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|---|---|
| Molecular Weight |
233.72
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| Exact Mass |
233.007
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| CAS # |
92-39-7
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| PubChem CID |
7088
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
15
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| Complexity |
236
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C(=C1)NC3=C(S2)C=CC(=C3)Cl
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| InChi Key |
KFZGLJSYQXZIGP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H8ClNS/c13-8-5-6-12-10(7-8)14-9-3-1-2-4-11(9)15-12/h1-7,14H
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| Chemical Name |
2-chloro-10H-phenothiazine
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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 | 4.2786 mL | 21.3931 mL | 42.7862 mL | |
| 5 mM | 0.8557 mL | 4.2786 mL | 8.5572 mL | |
| 10 mM | 0.4279 mL | 2.1393 mL | 4.2786 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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