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| 5mg |
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Felodipine 3,5-dimethyl ester is an aromatic dihydropyridine compound and a voltage-dependent L-type calcium channel modulator. The parent compound felodipine binds to and stabilizes the inactive conformation of L-type calcium channels in vascular smooth muscle cells, preventing calcium influx and subsequent vasoconstriction. This dimethyl ester analogue is likely to have a similar mechanism of action, inhibiting calcium-dependent myocyte contraction by binding to the alpha1 subunit of the L-type calcium channel. The compound also acts as a mineralocorticoid receptor modulator. However, as an impurity standard, it is not used for pharmacological studies [1L36-L37][11L28-L31].
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| ln Vitro |
No in vitro activity data is reported for this compound as a biological agent. It is not characterized for pharmacological potency (IC50, EC50) because it serves exclusively as an analytical reference standard for pharmaceutical quality control. Based on its structural similarity to felodipine (which has IC50 values in the 1-10 nM range for calcium channel blockade in vascular smooth muscle), the dimethyl ester analogue likely retains some calcium channel blocking activity, but no formal assays have been published. The compound is not intended for cell-based or enzyme assays for efficacy.
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| ln Vivo |
No in vivo activity data is available for felodipine 3,5-dimethyl ester as a stand-alone compound. It is not a therapeutic agent and is not administered to animals for efficacy studies. When present as an impurity in felodipine drug product at trace levels (typically <0.1-0.5% of the active ingredient), it is not expected to contribute to therapeutic or adverse effects. Felodipine itself has established in vivo efficacy as an antihypertensive in rat models (ED50 0.5-2 mg/kg oral). The dimethyl ester impurity is considered pharmacologically inert at the levels found in commercial drug products.
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| Enzyme Assay |
Not applicable, as this compound is an analytical impurity standard, not a drug candidate for enzyme assays. For analytical non-cellular characterization: dissolve felodipine 3,5-dimethyl ester in methanol to prepare 0.1-1.0 mg/mL stock solution. Analyze by reverse-phase HPLC (C18 column, 250×4.6 mm, 5 microm) with mobile phase: 0.1% phosphoric acid (A) and acetonitrile (B) in gradient (30-80% B over 30 min). Flow rate 1.0 mL/min, UV detection at 220 nm and 254 nm. Retention time ~10-15 min. Identify by comparison with a certified reference standard. For forced degradation studies, expose to light (1.2 million lux hours), heat (60degC, 48 h), and oxidation (3% H2O2, 2 h). Inject degraded samples into HPLC and monitor impurity profile [12L26-L27].
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| Cell Assay |
No cell-based biological assays are performed with felodipine 3,5-dimethyl ester as it is not a drug candidate. For impurity profiling of felodipine drug substance in pharmaceutical quality control: prepare felodipine sample at 1 mg/mL in mobile phase. Spike with felodipine 3,5-dimethyl ester reference standard at 0.1%, 0.5%, and 1.0% levels relative to felodipine. Separate by HPLC with C18 column. System suitability requires resolution ≥2.0 between felodipine and its impurity. Determine limit of detection (LOD) and quantitation (LOQ) based on signal-to-noise ratio (S/N=3 for LOD, S/N=10 for LOQ). LOD ~0.005%, LOQ ~0.015% relative to felodipine. Calibration curves are constructed using peak area vs concentration (0.05-5 microg/mL). Storage: -20degC, under inert atmosphere, protected from light [12L26-L27].
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| Animal Protocol |
Not applicable for animal studies with the purified impurity. For toxicology evaluation of felodipine drug substance, felodipine 3,5-dimethyl ester as an impurity is present at levels below 0.5% and is considered a process-related impurity with no significant pharmacological activity. No dedicated animal studies have been conducted using this isolated compound alone. For analytical research purposes, the compound may be used as a reference standard without animal administration. Its synthesis involves condensation of 2,3-dichlorobenzaldehyde with ethyl acetoacetate in the presence of piperidine, followed by reduction with sodium borohydride and esterification using methanol [11L41-L46].
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| ADME/Pharmacokinetics |
No pharmacokinetic data is available for felodipine 3,5-dimethyl ester as a stand-alone compound. It is not administered to animals or humans for PK studies. The parent compound felodipine has oral bioavailability of ~15%, reaches peak plasma levels in 2-5 h (Tmax), has a terminal half-life (t½) of 11-16 h, and is extensively metabolized by CYP3A4 to inactive carboxylic acid metabolites. By analogy, the dimethyl ester impurity, if ingested, would likely be rapidly metabolized by esterases and CYP enzymes, but formal studies are lacking. The compound is for research use only and not intended for systemic exposure.
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| Toxicity/Toxicokinetics |
No toxicity data is available for felodipine 3,5-dimethyl ester as a pure compound. In pharmaceutical quality control, the allowable limit of this impurity in felodipine and clevidipine drug substances is controlled based on ICH guidelines: any unspecified impurity ≤0.10%, total impurities ≤0.5%. The compound is not known to be genotoxic, carcinogenic, or teratogenic. Standard laboratory safety precautions apply: avoid inhalation, ingestion, and skin/eye contact. May cause respiratory tract and skin irritation. Use PPE (gloves, lab coat, safety goggles) and work in a well-ventilated fume hood. Waste disposal according to local regulations for pharmaceutical reference standards [12L28].
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| References | |
| Additional Infomation |
Felodipine 3,5-dimethyl ester is also known as Felodipine EP Impurity B, Felodipine Related Compound B, Clevidipine Impurity 3, and Dimethyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. CAS: 91189-59-2. Molecular formula C17H17Cl2NO4, MW 370.23. Melting point: 184-186degC. Appearance: pale yellow to light green solid. Solubility: chloroform (slightly), methanol (slightly). Storage: amber vial, -20degC freezer, under inert atmosphere. For research use only-not for human consumption. Purity typically ≥95%. Meets EP and USP standards for reference materials [12L26-L28][10L3-L9].
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| Molecular Formula |
C17H17CL2NO4
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| Molecular Weight |
370.23
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| Exact Mass |
369.053
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| CAS # |
91189-59-2
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| PubChem CID |
3378865
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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 |
5
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| Heavy Atom Count |
24
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| Complexity |
561
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CC1=C(C(C(=C(N1)C)C(=O)OC)C2=C(C(=CC=C2)Cl)Cl)C(=O)OC
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| InChi Key |
VEACAIASCBTOFS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H17Cl2NO4/c1-8-12(16(21)23-3)14(10-6-5-7-11(18)15(10)19)13(9(2)20-8)17(22)24-4/h5-7,14,20H,1-4H3
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| Chemical Name |
dimethyl 4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
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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 | 2.7010 mL | 13.5051 mL | 27.0102 mL | |
| 5 mM | 0.5402 mL | 2.7010 mL | 5.4020 mL | |
| 10 mM | 0.2701 mL | 1.3505 mL | 2.7010 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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