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| Other Sizes |
| Targets |
Fluphenazine-N-2-chloroethane hydrochloride targets dopamine D2 receptors (DRD2) and calmodulin (CaM). Fluphenazine-N-2-chloroethane irreversibly binds to D2 receptors, acting as a selective, irreversible antagonist (IC50 = 100 nM for D2). The parent compound fluphenazine binds the dopamine D2 receptor with high affinity (Ki = 0.55 nM). It also irreversibly inhibits calmodulin at higher doses (IC50 = 10 uM), which can disrupt calcium-dependent signaling pathways. The alkylating chlorethylamine chain produces irreversible protein binding, making it useful for long-term receptor inactivation studies.
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| ln Vitro |
Fluphenazine-N-2-chloroethane hydrochloride (10 µM) can reduce the NO production induced by 0.1 mM CORM-2 (HY-W033577) in acinar cells [2].
In vitro, Fluphenazine-N-2-chloroethane hydrochloride is a potent irreversible calmodulin antagonist and a selective irreversible antagonist of D2 receptors. It exhibits significant anticancer activity across various human cancer cell lines. At 10 uM, the compound reduces nitric oxide (NO) production induced by 0.1 mM CORM-2 in acinar cells. The compound's unique properties arise from its irreversible binding and dual action on dopamine receptors and calmodulin. No specific IC50 values for anticancer activity are reported. |
| ln Vivo |
No specific in vivo activity data for Fluphenazine-N-2-chloroethane hydrochloride are reported in the search results. As an irreversible D2 antagonist, it has potential for use in animal models of Parkinson‘s disease, schizophrenia, and pituitary tumors. However, due to the irreversible alkylation, it would likely cause long-lasting effects and toxicity. The compound is a research tool for in vitro studies. No specific in vivo studies are described.
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| Enzyme Assay |
The binding of Fluphenazine-N-2-chloroethane to D2 receptors is measured by radioligand binding assays using membrane preparations from cells expressing D2 receptors. The compound is incubated with the membranes and a radiolabeled D2 antagonist (e.g., [3H]spiperone or [3H]N-methylspiperone). After incubation, unbound ligand is removed, and bound radioactivity is measured by scintillation counting. The IC50 for D2 binding is 100 nM. For calmodulin inhibition, a standard calmodulin-dependent phosphodiesterase (PDE) activity assay is used: calmodulin, PDE, and the substrate cAMP are incubated with the compound, and the production of 5‘-AMP is measured. The irreversible nature is confirmed by washing the membranes after incubation and showing that binding is not reversed.
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| Cell Assay |
For cellular assays, cancer cell lines (e.g., HeLa, MCF-7) are seeded in 96-well plates. Cells are treated with Fluphenazine-N-2-chloroethane hydrochloride at graded concentrations (0.1-100 uM) for 24-72 hours. Cell viability is measured by MTT or CellTiter-Glo assays to assess anticancer activity. For D2 receptor studies, cells expressing D2 receptors (e.g., transfected HEK293 cells) are pre-treated with the compound, then washed extensively, and [3H]spiperone binding is measured. For calmodulin studies, cells are treated, and calmodulin activity in cell lysates is measured using a calmodulin-dependent PDE activity assay.
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| Animal Protocol |
No animal experiments for Fluphenazine-N-2-chloroethane hydrochloride are described in the search results. For in vivo evaluation of D2 receptor inactivation, the compound would be administered to rats via intracerebroventricular (ICV) injection. The irreversible binding would allow for long-term studies of D2 receptor function, as the effect would last until new receptors are synthesized. However, due to its potential toxicity and irreversible binding, it is not commonly used in vivo.
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| ADME/Pharmacokinetics |
Fluphenazine-N-2-chloroethane hydrochloride (C22H2₇Cl3F3N3S, MW = 528.89, purity 95.5% by HPLC, CAS 3892-78-2) is a solid powder (white to off-white). For storage, the powder should be kept at -20degC for up to 3 years, sealed and protected from light. For in vitro use, stock solutions in DMSO (100 mg/mL, 189.1 mM) can be prepared and stored at -80degC for up to 6 months or at -20degC for 1 month. For in vivo use, it can be formulated in 10% DMSO / 40% PEG300 / 5% Tween-80 / 45% saline. No detailed PK parameters are reported.
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| Toxicity/Toxicokinetics |
No specific toxicity data for Fluphenazine-N-2-chloroethane hydrochloride are reported. As an alkylating agent, it is likely to be genotoxic and potentially carcinogenic. It is an irritant and should be handled with extreme caution. The compound is not intended for human or veterinary use. Standard laboratory safety precautions for handling alkylating agents should be followed, including the use of gloves, lab coat, safety goggles, and working in a fume hood. No LD50 or formal toxicology studies are available.
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| References |
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| Additional Infomation |
Fluphenazine-N-2-chloroethane hydrochloride (SKF-7171A) is an alkylating derivative of the antipsychotic drug fluphenazine. The parent compound fluphenazine is a typical antipsychotic that tightly binds the dopamine D2 receptor (Ki = 0.55 nM) and is used to treat schizophrenia. The alkylating chlorethylamine chain (nitrogen mustard) in Fluphenazine-N-2-chloroethane produces irreversible protein binding, similar to the mechanism of alkylating chemotherapy drugs. This allows the compound to irreversibly inactivate D2 receptors and calmodulin, making it a valuable research tool for long-term receptor inactivation studies. The compound also exhibits significant anticancer activity across various human cancer cell lines, likely through its effects on calmodulin and D2 receptors. The compound is for research use only and has no clinical applications.
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| Molecular Formula |
C22H27CL3F3N3S
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|---|---|
| Molecular Weight |
528.89
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| Exact Mass |
491.118
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| CAS # |
3892-78-2
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| PubChem CID |
9550045
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| Appearance |
White to off-white solid powder
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| Density |
1.274g/cm3
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| Boiling Point |
553.2ºC at 760 mmHg
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| Flash Point |
288.3ºC
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| Index of Refraction |
1.571
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| LogP |
6.297
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
31
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| Complexity |
544
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| Defined Atom Stereocenter Count |
0
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| SMILES |
Cl.ClCCN1CCN(CCCN2C3=CC=CC=C3SC3C=CC(=CC2=3)C(F)(F)F)CC1
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| InChi Key |
KGXTXMNKUAOQHG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C22H25ClF3N3S.ClH/c23-8-11-28-14-12-27(13-15-28)9-3-10-29-18-4-1-2-5-20(18)30-21-7-6-17(16-19(21)29)22(24,25)26;/h1-2,4-7,16H,3,8-15H2;1H
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| Chemical Name |
10-[3-[4-(2-chloroethyl)piperazin-1-yl]propyl]-2-(trifluoromethyl)phenothiazine;hydrochloride
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| Synonyms |
SKF-7171A hydrochloride
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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) |
DMSO : 10 mg/mL (18.91 mM; with sonication and heat)
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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 | 1.8908 mL | 9.4538 mL | 18.9075 mL | |
| 5 mM | 0.3782 mL | 1.8908 mL | 3.7815 mL | |
| 10 mM | 0.1891 mL | 0.9454 mL | 1.8908 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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