![(2S,4R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoate hydrochloride](/upload/0319/V121012.png)
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| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
The compound itself does not have a direct pharmacological target as it is a synthetic intermediate. However, the structural class it belongs to-specifically the 4-amino-2-methylpentanoate backbone with a biphenyl substituent-is designed to interact with neprilysin (NEP), a zinc-dependent metalloprotease that degrades natriuretic peptides, including atrial natriuretic peptide (ANP) and brain natriuretic peptide (BNP). Inhibition of neprilysin increases the levels of these vasoactive peptides, leading to vasodilation, natriuresis, and diuresis. The (2R,4S) stereoisomer (the enantiomer of the side chain in the final drug) is known to have potent neprilysin inhibitory activity.
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| ln Vitro |
(2S,4R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoate hydrochloride does not possess intrinsic in vitro biological activity itself, as it is a synthetic intermediate and impurity reference standard rather than an active drug. Its purpose is to serve as a chemical building block in the synthesis of active neprilysin inhibitors, which are then evaluated in biochemical enzyme inhibition assays. In those active compounds, the in vitro activity against recombinant human neprilysin is measured using fluorogenic substrates such as Mca-RPPGFSAFK(Dnp)-OH, and IC50 values in the low nanomolar range are typical for fully elaborated neprilysin inhibitors.
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| ln Vivo |
In vivo activity is not associated with this intermediate itself but rather with the final drug products into which it is incorporated. Sacubitril, the neprilysin inhibitor component of Entresto, when administered in combination with valsartan, demonstrates significant cardiovascular benefits in animal models of heart failure. In rats with heart failure induced by myocardial infarction, sacubitril/valsartan (LCZ696) reduces left ventricular end-diastolic pressure, decreases cardiac fibrosis, and improves survival compared to either component alone. Clinical studies have shown that sacubitril/valsartan reduces the risk of cardiovascular death or heart failure hospitalization in patients with heart failure with reduced ejection fraction (HFrEF).
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| Enzyme Assay |
Non-cellular experiments involving this compound are primarily analytical in nature for impurity profiling. A typical HPLC method for monitoring the content of (2S,4R)-Ethyl 5-([1,1'-biphenyl]-4-yl)-4-amino-2-methylpentanoate hydrochloride uses a C18 reverse-phase column (e.g., 4.6 mm × 250 mm, 5 microm particles) with a mobile phase consisting of a mixture of acetonitrile and phosphate buffer (pH 3.0) delivered at 1.0 mL/min. Detection is by UV absorbance at 210 nm or 254 nm. The compound is prepared as a reference standard in methanol or acetonitrile at a concentration of 1.0 mg/mL. LC-MS/MS in positive ion mode can be applied for trace-level impurity quantification following ICH guidelines.
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| Cell Assay |
Cell-based assays are not applicable for this intermediate, as it is a synthetic building block and impurity standard. The compound is designed for chemical transformation, not for direct cellular interaction. The presence of the free amino group and ethyl ester makes it a polar molecule that may not efficiently cross cell membranes. Any cell-based evaluations of neprilysin inhibitory activity would be conducted on the final deprotected active compounds (the free carboxylic acids) after the ethyl ester has been hydrolyzed to the active form.
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| Animal Protocol |
In vivo animal studies are not applicable for this synthetic intermediate. The parent drugs derived from similar intermediates have been extensively tested. A typical study of the neprilysin inhibitor sacubitril in rats involves oral administration at doses ranging from 10 to 100 mg/kg. Blood samples are collected at predetermined time points, and the concentration of the active metabolite (sacubitrilat, the free carboxylic acid form) is measured by LC-MS/MS. In heart failure models, endpoints include echocardiographic assessment of left ventricular ejection fraction, measurement of natriuretic peptide levels, and histological analysis of cardiac tissue.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties are not available for this synthetic intermediate, as it is not a therapeutic agent. The ethyl ester of this compound (which is characteristic of prodrug design) is designed to enhance oral absorption. Following oral administration, the ethyl ester is rapidly hydrolyzed by carboxylesterases in the liver and gut to the active free carboxylic acid metabolite (the neprilysin inhibitor). This strategy improves bioavailability. The compound is typically stored at -20degC in a freezer to maintain stability, and it should be protected from light and moisture.
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| Toxicity/Toxicokinetics |
The toxicological profile of this compound has not been fully characterized, as it is a research-use-only intermediate and impurity standard. Based on its structural features-a primary amine and an ethyl ester-standard chemical safety precautions apply. It may cause skin and eye irritation and may be harmful if swallowed, inhaled, or absorbed through the skin. The hydrochloride salt form makes it water-soluble. It should be handled in a well-ventilated area (fume hood) while wearing appropriate personal protective equipment (lab coat, gloves, safety goggles).
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| Additional Infomation |
Additional information: This compound has a molecular weight of 347.88 g/mol and a purity of 97-98% when sold as a research reagent. Its IUPAC name is ethyl (2S,4R)-5-(4-phenylphenyl)-4-aminopentanoate hydrochloride. Other names include (2S,4R)-ethyl 5-(biphenyl-4-yl)-4-aminopentanoate hydrochloride. The compound is available in various quantities (10 mg, 25 mg, 100 mg, etc.) from commercial suppliers for research use only. It should be stored under inert atmosphere at -20degC for long-term stability.
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| Molecular Formula |
C20H26CLNO2
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| Molecular Weight |
347.88
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| CAS # |
2259707-96-3
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| Appearance |
Typically exists as solids at room temperature
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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 | 2.8746 mL | 14.3728 mL | 28.7455 mL | |
| 5 mM | 0.5749 mL | 2.8746 mL | 5.7491 mL | |
| 10 mM | 0.2875 mL | 1.4373 mL | 2.8746 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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