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| 1mg |
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| 5mg |
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| Targets |
The primary target of Pipendoxifene hydrochloride is the estrogen receptor (ER), specifically ER-alpha. As a selective estrogen receptor modulator (SERM), it binds to estrogen receptors and modulates their transcriptional activity. In the context of breast cancer, Pipendoxifene hydrochloride acts as an estrogen antagonist, inhibiting estrogen-dependent cell proliferation. It inhibits estrogen binding to ER-alpha with an IC50 of 14 nM. The compound's mechanism involves competitive binding to the estrogen receptor, blocking the action of endogenous estrogens. Its improved selectivity over other SERMs may contribute to a reduced side effect profile.
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| ln Vitro |
Pipendoxifene is an innovative 2-phenylindole selective estrogen receptor modulator (SERM) that has been chosen for additional research to treat metastatic breast cancer due to its superior preclinical pharmacology characteristics [1].
In vitro, Pipendoxifene hydrochloride has demonstrated anti-proliferative effects in breast cancer cell lines, including tamoxifen-resistant cells. It inhibits estrogen-dependent cell proliferation by binding to estrogen receptors and modulating their transcriptional activity. The compound inhibits estrogen binding to ER-alpha with an IC50 of 14 nM. Its activity in tamoxifen-resistant cell lines suggests that it may overcome resistance mechanisms associated with other SERMs. Pipendoxifene hydrochloride has been studied for its potential in treating metastatic breast cancer. Its in vitro activity supports its potential as a therapeutic agent for estrogen-dependent cancers. |
| ln Vivo |
In vivo, Pipendoxifene hydrochloride has been studied in preclinical models of breast cancer. Preclinical studies indicated favorable pharmacokinetics and a good safety profile. The compound has demonstrated antitumor activity in animal models of estrogen-dependent breast cancer. Its improved selectivity may reduce typical SERM-related side effects, such as endometrial hyperplasia and thromboembolic events. Although development did not advance further, the compound remains valuable for studying next-generation SERM mechanisms. Further in vivo studies would be needed to fully characterize its efficacy and safety profile.
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| Enzyme Assay |
The in vitro binding activity of Pipendoxifene hydrochloride can be assessed using cell-free receptor binding assays. A typical protocol involves incubating the compound with recombinant ER-alpha or ER-beta protein and a radiolabeled estrogen ligand (e.g., [3H]-estradiol) in a binding buffer. The reaction is carried out at 4degC for 16-24 hours. Bound and free ligand are separated by charcoal adsorption or filtration, and the radioactivity is measured by scintillation counting. The IC50 value is determined by plotting the percentage of specific binding remaining against the compound concentration. The selectivity of the compound for ER-alpha over ER-beta can be assessed using similar assays with each receptor isoform.
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| Cell Assay |
For in vitro cellular experiments, breast cancer cell lines (e.g., MCF-7, T47D) are cultured in estrogen-depleted media and treated with Pipendoxifene hydrochloride at various concentrations (typically 0.1-100 microM). After treatment, cell proliferation is measured using MTT, BrdU incorporation, or other cell proliferation assays. Estrogen receptor-mediated transcriptional activity is assessed using luciferase reporter assays, where cells are transfected with an estrogen-responsive element (ERE)-luciferase construct and treated with the compound in the presence or absence of estradiol. Gene expression changes (e.g., estrogen-responsive genes such as pS2, PR) are assessed by qRT-PCR or Western blot.
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| Animal Protocol |
In vivo animal experiments with Pipendoxifene hydrochloride would typically involve oral administration in mouse models of breast cancer. A common protocol involves subcutaneous implantation of estrogen-dependent breast cancer cells (e.g., MCF-7) in immunodeficient mice, followed by oral administration of the compound at various doses (e.g., 1-50 mg/kg) once daily. Tumor growth is monitored by caliper measurements, and the compound's effect on tumor growth and survival is assessed. Endometrial thickness and other SERM-related side effects are evaluated by histological analysis. Pharmacokinetic and toxicity studies are also performed to characterize its safety profile.
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| ADME/Pharmacokinetics |
Pipendoxifene hydrochloride has demonstrated favorable pharmacokinetics in preclinical studies. Following oral administration, it is absorbed and distributed to target tissues. The compound has a molecular weight of 493.04 g/mol. Its pharmacokinetic profile is characterized by dose-dependent exposure and a moderate half-life. Preclinical studies indicated a good safety profile, with reduced SERM-related side effects compared to other SERMs. The compound is metabolized in the liver and excreted in the bile and urine. Further studies would be needed to fully characterize its pharmacokinetic properties in humans.
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| Toxicity/Toxicokinetics |
Pipendoxifene hydrochloride has demonstrated a good safety profile in preclinical studies. Its improved selectivity may reduce typical SERM-related side effects, such as endometrial hyperplasia, hot flashes, and thromboembolic events. However, as with any SERM, potential toxicities may include effects on bone density, cardiovascular function, and reproductive tissues. The compound has been evaluated in early clinical studies but did not advance to regulatory approval. The compound should be handled with standard laboratory precautions and is intended for research use only.
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| References | |
| Additional Infomation |
Pipendoxifene hydrochloride (ERA923 hydrochloride) is a selective estrogen receptor modulator (SERM) developed for the treatment of breast cancer. It acts as an estrogen antagonist that binds to estrogen receptors and modulates their transcriptional activity to inhibit estrogen-dependent cell proliferation. The compound inhibits estrogen binding to ER-alpha with an IC50 of 14 nM. Pipendoxifene hydrochloride has demonstrated anti-proliferative effects in tamoxifen-resistant cell lines and improved selectivity that may reduce typical SERM-related side effects. Although development did not advance further, it remains valuable for studying next-generation SERM mechanisms. It is available as a research compound and is not approved for clinical use.
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| Molecular Formula |
C29H33CLN2O3
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|---|---|
| Molecular Weight |
493.0369
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| Exact Mass |
492.217
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| CAS # |
245124-69-0
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| Related CAS # |
Pipendoxifene;198480-55-6
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| PubChem CID |
11755428
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| Appearance |
White to yellow solid powder
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
35
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| Complexity |
611
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=C(N(C2=C1C=C(C=C2)O)CC3=CC=C(C=C3)OCCN4CCCCC4)C5=CC=C(C=C5)O.Cl
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| InChi Key |
FIKCMRKZNTXMKE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C29H32N2O3.ClH/c1-21-27-19-25(33)11-14-28(27)31(29(21)23-7-9-24(32)10-8-23)20-22-5-12-26(13-6-22)34-18-17-30-15-3-2-4-16-30;/h5-14,19,32-33H,2-4,15-18,20H2,1H3;1H
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| Chemical Name |
2-(4-hydroxyphenyl)-3-methyl-1-[[4-(2-piperidin-1-ylethoxy)phenyl]methyl]indol-5-ol;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 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 : ~100 mg/mL (~202.82 mM)
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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 | 2.0282 mL | 10.1412 mL | 20.2823 mL | |
| 5 mM | 0.4056 mL | 2.0282 mL | 4.0565 mL | |
| 10 mM | 0.2028 mL | 1.0141 mL | 2.0282 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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