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| Other Sizes |
| Targets |
Benproperine phosphate targets ARPC2 (actin-related protein 2/3 complex subunit 2), a component of the Arp2/3 complex that plays a critical role in actin polymerization and cytoskeletal dynamics. By inhibiting ARPC2, the compound disrupts actin cytoskeleton organization, which may affect cell migration, invasion, and other actin-dependent cellular processes. As an antitussive, it is believed to act centrally to suppress the cough reflex.
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| ln Vitro |
In a dose-dependent manner, benproperine phosphate (20–120 μM) reduces cell viability for 24 hours [1]. Benproperine phosphate (10 μM; 24 hours of action) has an IC50 value of 1-2 μM and strongly inhibits the migration of different cancer cells, as well as the migration and invasion of DLD-1 and AsPC-1 cells. In MCF-10A cells, benproperine phosphate (10 μM; 24 hours) has no effect on cortactin-rich lamellipodia [1].
In vitro, Benproperine phosphate inhibits ARPC2, a component of the Arp2/3 complex involved in actin polymerization. The compound's ability to disrupt actin cytoskeleton dynamics makes it a valuable tool for studying cell migration and invasion. Its antitussive activity is likely mediated through central mechanisms suppressing the cough reflex. |
| ln Vivo |
The growth of primary pancreatic tumors is inhibited by benproperine phosphate (50, 100 mg/kg; oral gavage; 5 days per week for 4 weeks)[1]. Benproperine phosphate (56.1% inhibition) dramatically decreased the lung metastasis of mouse AsPC-1 cells. Benproperine phosphate reduced HCT-116 and DLD-1 cells' ability to spread to the liver by 78.9% and 78.2%, respectively[1].
In vivo, Benproperine phosphate (50, 100 mg/kg; oral gavage; 5 days per week for 4 weeks) inhibits primary pancreatic tumor growth. This demonstrates the compound's in vivo anti-tumor efficacy in a pancreatic cancer model. As an antitussive, it increases the latency to first cough and decreases the number of coughs during and after a citric acid aerosol challenge. |
| Enzyme Assay |
For non-cellular in vitro assays, Benproperine phosphate is evaluated for its binding affinity to ARPC2 and the Arp2/3 complex. The compound is incubated with purified Arp2/3 complex or ARPC2, and binding is measured using surface plasmon resonance or other biophysical techniques. The compound's ability to inhibit actin polymerization may be assessed using actin polymerization assays.
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| Cell Assay |
Cell Viability Assay[1]
Cell Types: DLD-1, AsPC-1, CFPAC-1, A375P, A375P, MDA-MB-231, DU145, DU145 cancer cells Tested Concentrations: 20, 40, 60, 80, 100, 120 μM Incubation Duration:For 24 hrs (hours) Experimental Results: Inhibited cell viability in a dose-dependent manner. For in vitro cellular assays, Benproperine phosphate is tested in cancer cell lines to assess its effects on cell migration, invasion, and proliferation. Cells are treated with serial dilutions of the compound, and cell migration and invasion are assessed using transwell or scratch wound healing assays. Actin cytoskeleton organization is examined by immunofluorescence staining. Cell viability and proliferation are measured using standard assays. |
| Animal Protocol |
Animal/Disease Models: Female BALB/c nude mice of 6weeks old with AsPC-1 cells[1]
Doses: 50, 100 mg/kg Route of Administration: Oral gavage; 5 days per week for 4 weeks Experimental Results: Inhibited primary pancreatic tumor growth compared to the vehicle control (47.7% inhibition) without body weights change. For in vivo animal studies, Benproperine phosphate is evaluated in mouse models of pancreatic cancer. Mice bearing established pancreatic tumors are treated with the compound via oral gavage at doses of 50 or 100 mg/kg, 5 days per week for 4 weeks. Tumor growth inhibition is assessed by measuring tumor volumes. Antitussive activity is evaluated in cough models using citric acid aerosol challenge. |
| ADME/Pharmacokinetics |
Pharmacokinetic data for Benproperine phosphate are limited. As a small-molecule compound with a molecular weight of 407.44, it is expected to have favorable oral bioavailability. The compound is administered orally as an antitussive, indicating good oral absorption. Further pharmacokinetic studies would be needed to fully characterize its absorption, distribution, metabolism, and excretion profile.
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| Toxicity/Toxicokinetics |
Toxicological data for Benproperine phosphate are limited to its use as an approved antitussive agent. As a pharmaceutical, it has undergone safety evaluations for its indicated use. Comprehensive toxicology studies would be required for new therapeutic indications such as cancer treatment. The compound is for research use only and not for human use outside of approved indications.
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| References | |
| Additional Infomation |
See also: Amphetamine (note moved to).
Benproperine phosphate is an antitussive agent and ARPC2 inhibitor with a molecular formula of C₂₁H₃₀NO₅P and a molecular weight of 407.44. It is used in the treatment of acute and dry cough and inhibits primary pancreatic tumor growth in vivo (50, 100 mg/kg; oral gavage; 5 days per week for 4 weeks). The compound increases the latency to first cough and decreases the number of coughs. |
| Molecular Formula |
C21H30NO5P
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|---|---|
| Molecular Weight |
407.44
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| Exact Mass |
407.186
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| Elemental Analysis |
C, 61.91; H, 7.42; N, 3.44; O, 19.63; P, 7.60
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| CAS # |
19428-14-9
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| Related CAS # |
2156-27-6; 19428-14-9; 3563-76-6
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| PubChem CID |
167811
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| Appearance |
White to off-white solid powder
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| Boiling Point |
433ºC at 760mmHg
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| Melting Point |
148-153ºC
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| Vapour Pressure |
1.06E-07mmHg at 25°C
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| LogP |
3.539
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
28
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| Complexity |
370
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC(COC1=CC=CC=C1CC2=CC=CC=C2)N3CCCCC3.OP(=O)(O)O
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| InChi Key |
MCVUURBOSHQXMK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C21H27NO.H3O4P/c1-18(22-14-8-3-9-15-22)17-23-21-13-7-6-12-20(21)16-19-10-4-2-5-11-19;1-5(2,3)4/h2,4-7,10-13,18H,3,8-9,14-17H2,1H3;(H3,1,2,3,4)
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| Chemical Name |
1-[1-(2-benzylphenoxy)propan-2-yl]piperidine;phosphoric acid
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| Synonyms |
Benproperine phosphate; ASA 158-5; 19428-14-9; Pirexyl; Benproperine trihydrogen phosphate; S831Z48C5W; ASA158-5; ASA-158-5; BPP
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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 Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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: 125 mg/mL (306.79 mM)
H2O: ≥ 100 mg/mL (245.43 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.11 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 (5.11 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (5.11 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4543 mL | 12.2717 mL | 24.5435 mL | |
| 5 mM | 0.4909 mL | 2.4543 mL | 4.9087 mL | |
| 10 mM | 0.2454 mL | 1.2272 mL | 2.4543 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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