| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
L-type voltage-gated calcium channels (Cav1.2). (R)-Nicardipine binds to the 1,4-dihydropyridine (DHP) binding site on the alpha-1C subunit of the L-type calcium channel. It is described as the less active R enantiomer (compared to the racemate), with the racemic form of nicardipine showing an IC50 of approximately 1 uM for blocking cardiac calcium channels. It is more potent than the (S)-enantiomer but less potent than the racemic mixture, which is likely the most active form.
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| ln Vitro |
In vitro, (R)-Nicardipine inhibits calcium channel activity in a concentration-dependent manner. It relaxes vascular smooth muscle by inhibiting calcium influx through L-type voltage-gated calcium channels, leading to reduced intracellular calcium concentration and vasodilation. It is used as a reference compound for stereospecific binding studies on dihydropyridine calcium channel blockers. In functional assays such as the inhibition of contractile responses of isolated rabbit aortic rings to depolarizing stimuli, the (R)-enantiomer demonstrates greater potency than the (S)-enantiomer but less potency than the racemate.
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| ln Vivo |
No in vivo studies have been reported for the isolated (R)-enantiomer of nicardipine. The racemic formulation of nicardipine is clinically used as an antihypertensive and anti-anginal agent, with effects mediated by both enantiomers, potentially with contribution from (R)-nicardipine. (R)-Nicardipine itself is not intended for therapeutic use in its isolated form, as the racemate provides the optimal pharmacological profile. It may exhibit some stereoselective differences in pharmacokinetics, but detailed in vivo data are lacking.
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| Enzyme Assay |
Non-cellular binding assays are performed using membrane preparations from cells expressing rat or human L-type calcium channel subunits (e.g., HEK293 cells expressing Cav1.2 + alpha2delta + beta subunits). Membranes are incubated with the radiolabeled DHP antagonist [3H]-PN200-110 (or [3H]-nitrendipine, 0.1-1 nM) and varying concentrations of (R)-Nicardipine (0.1-1000 nM) in 50 mM Tris-HCl buffer (pH 7.4) containing 0.1 mM PMSF and 0.1% BSA for 60-90 minutes at 25degC. Non-specific binding is determined with 1 uM nifedipine. Bound radioactivity is separated by filtration through GF/B filters using a cell harvester and counted by liquid scintillation. IC50 and Ki values are calculated from competition curves, with the racemate showing an IC50 of about 1 uM.
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| Cell Assay |
Whole-cell patch clamp electrophysiology assays are performed on HEK293 cells stably expressing human Cav1.2 channels (alpha1C, beta2a, alpha2delta-1 subunits). The whole-cell patch clamp technique in voltage-clamp mode is used to record barium (Ba2+) currents through L-type calcium channels. Cells are held at a holding potential of -80 mV and stepped to a test potential of +10 mV for 200 ms every 10 seconds. (R)-Nicardipine is applied extracellularly via perfusion at increasing concentrations (0.01-100 uM) until a steady-state block is achieved. The IC50 is determined from the concentration-inhibition curve and compared to that of the racemate and (S)-enantiomer. Alternatively, calcium influx assays using calcium-sensitive dyes (e.g., Fluo-4-AM) in FLIPR format can be used.
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| Animal Protocol |
Not applicable for the isolated enantiomer. For the racemic mixture, standard in vivo protocols involve anesthetized normotensive or spontaneously hypertensive rats. Nicardipine (0.1-3 mg/kg) is administered intravenously or orally, and mean arterial blood pressure (MAP) is monitored continuously via a carotid artery catheter. Heart rate is also recorded using electrocardiography (ECG). The antihypertensive effect is evaluated as the maximum reduction in MAP and the duration of action. The (R)-enantiomer itself is not used in animal efficacy studies.
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| ADME/Pharmacokinetics |
No pharmacokinetic data have been reported for the isolated (R)-enantiomer. The racemic form of nicardipine is well-characterized: it is rapidly absorbed after oral administration with a bioavailability of 20-35% due to extensive first-pass metabolism, reaching peak plasma concentration within 30-60 minutes. It is highly (∼95%) bound to plasma proteins. It is extensively metabolized by CYP3A4, with a terminal half-life (t½) of 2-4 hours. The enantiomers may exhibit stereoselective metabolism; however, detailed PK parameters for the individual (R)-enantiomer have not been separately reported.
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| Toxicity/Toxicokinetics |
No toxicity data are specifically reported for the isolated (R)-enantiomer. Racemic nicardipine has an established safety profile based on decades of clinical use. Common adverse effects include peripheral edema, headache, dizziness, flushing, and palpitations. Rare but serious side effects include reflex tachycardia, hypotension, and exacerbation of heart failure. At therapeutic concentrations, no significant genotoxicity, carcinogenicity, or reproductive toxicity has been observed in animal studies. The (R)-enantiomer is not expected to have a safety profile distinctly different from the racemate.
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| References | |
| Additional Infomation |
(R)-nicardipine is the R-enantiomer of nicardipine. It is an antihypertensive drug and a calcium channel blocker. It is the enantiomer of (S)-nicardipine.
(R)-Nicardipine is a research chemical used for stereochemical structure-activity relationship (SAR) studies of dihydropyridine calcium channel blockers. It is not a clinically approved drug for therapeutic use, as the racemic formulation of nicardipine is the approved pharmaceutical agent. This enantiomer serves as a reference compound for stereoselective drug metabolism and action studies. It is available from chemical suppliers for research purposes only, and no regulatory agency has approved it for human consumption. It is often used in conjunction with (S)-Nicardipine for comparative chiral pharmacology experiments. |
| Molecular Formula |
C26H29N3O6
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|---|---|
| Molecular Weight |
479.5250
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| Exact Mass |
479.205
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| CAS # |
76093-35-1
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| Related CAS # |
Nicardipine hydrochloride;54527-84-3;Nicardipine-d3 hydrochloride;1432061-50-1;(S)-Nicardipine;76093-36-2;(R)-Nicardipine-d3;Nicardipine;55985-32-5
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| PubChem CID |
6603948
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| Appearance |
Off-white to light yellow solid powder
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| LogP |
3.8
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
10
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| Heavy Atom Count |
35
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| Complexity |
856
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O(C([H])([H])C([H])([H])N(C([H])([H])[H])C([H])([H])C1C([H])=C([H])C([H])=C([H])C=1[H])C(C1=C(C([H])([H])[H])N([H])C(C([H])([H])[H])=C(C(=O)OC([H])([H])[H])[C@@]1([H])C1C([H])=C([H])C([H])=C(C=1[H])[N+](=O)[O-])=O
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| InChi Key |
ZBBHBTPTTSWHBA-XMMPIXPASA-N
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| InChi Code |
InChI=1S/C26H29N3O6/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19/h5-12,15,24,27H,13-14,16H2,1-4H3/t24-/m1/s1
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| Chemical Name |
5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl (4R)-2,6-dimethyl-4-(3-nitrophenyl)-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) |
DMSO : ~200 mg/mL (~417.08 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 | 2.0854 mL | 10.4269 mL | 20.8538 mL | |
| 5 mM | 0.4171 mL | 2.0854 mL | 4.1708 mL | |
| 10 mM | 0.2085 mL | 1.0427 mL | 2.0854 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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